Nestled between the rolling hills of Tuscany, Val di Chiana is a picturesque tapestry of medieval villages, sprawling vineyards, and sun-drenched landscapes that beckon travelers to explore its charm. The area's rich culinary heritage, celebrated through its renowned wines and hearty local fare, pairs beautifully with stunning architecture that ranges from ancient castles to elegant Renaissance palaces. Within this enchanting backdrop lies an exceptional selection of boutique hotels that embody the essence of this region. At Stelle di Monte, guests can indulge in breathtaking views and rustic elegance, while Podere Le Volte Country House La Mita offers a serene escape amidst olive groves and vineyards, perfect for those seeking tranquility. For a unique experience, Lupaia stands out with its stylish design and personalized service, immersing visitors in the local culture. Together, these Val di Chiana boutique hotels with entertainment promise not just a place to rest, but a memorable journey into the heart of Tuscany. Browse our collection or start planning your escape today!
Exceptional
90 reviews
Nestled amidst the rolling hills of Montepulciano, Stelle di Monte is a romantic hideaway that feels like a painter's dream. Here, luxury meets the tranquility of nature, where beautifully restored historical architecture harmonizes with breathtaking garden views, creating an intimate ambiance perfect for couples and seekers of serene respite.
Romantic Escape - Whisk away your senses in this enchanting sanctuary, where candlelit dinners beneath the stars transform into unforgettable moments against a backdrop of panoramic vistas—the perfect setting for love to blossom.
Culinary Delights - Savor each culinary experience in our charming restaurant, where fragrant herbs mingle with the aroma of expertly crafted French cuisine—each dish prepared with care by chef Igor, ensuring every meal is a work of art.
Historic Elegance - Experience the blend of tradition and modern comfort in elegantly appointed rooms featuring plush bedding and inviting textures, while the rich history of the villa whispers tales of times gone by, inviting you to linger just a little longer.
Guest Experiences - As dawn breaks, the soft scent of warm pancakes wafts through the air, coaxing guests from their luxurious linens to a delightful breakfast spread—where laughter often mingles with the enchanting chirp of birds serenading the morning sun.
Exceptional
104 reviews
Nestled in the serene hills of Civitella in Val di Chiana, Podere Le Volte Country House La Mita is a captivating retreat where time slows down amid rustic elegance and breathtaking landscapes. Here, the air is infused with the scent of blossoming gardens and the warmth of genuine Italian hospitality, making it an idyllic destination for couples seeking romance or wellness enthusiasts yearning for tranquility.
Total Relaxation - Unwind by the sparkling pool surrounded by lush gardens, where comfortable cabanas invite you to linger in the sun-dappled shade and sip on a refreshing drink while listening to the gentle rustle of leaves.
Culinary Delights - Savor homemade Italian dishes crafted from fresh local ingredients, where the aroma of basil and ripe tomatoes fills the air as you indulge in a meal that promises unforgettable flavors—don't miss the legendary tiramisu, said to be the best in Italy.
Country Escape - Bask in the tranquil ambiance of this family-run agriturismo, where every corner tells a story, from the charmingly decorated rooms to the scenic walking paths that beckon you to explore the stunning countryside.
Guest Experiences - As you stroll through the garden, the laughter of fellow travelers mingles with birdsong, and the delightful fragrance of blooming flowers envelops you, creating a tapestry of peace where even the little imperfections—like the occasional hiccup in service—are softened by the warmth of the hosts' smiles.
Exceptional
134 reviews
Perched elegantly on a Tuscan hilltop, Lupaia is an enchanting retreat where rustic charm meets refined luxury. As the sun dips below the rolling hills, the golden light dances off beautifully hand-painted walls and original wooden beams, inviting you to unwind in the embrace of this idyllic sanctuary.
Romantic Break - Whisk your loved one away to a captivating haven, where every corner radiates intimacy—from private terraces adorned with fragrant blooms to evenings spent under starlit skies, savoring exquisite local wines and delectable Tuscan dishes.
Total Relaxation - Nestled amidst verdant landscapes, the hillside outdoor swimming pool beckons with its shimmering waters, the gentle sound of nature surrounding you as you bask in the tranquility of this secluded paradise.
Local Markets - Immerse yourself in the flavors of Tuscany as you stroll through nearby markets, selecting fresh produce and artisanal cheeses that inspire the restaurant's daily changing menu, making each meal a celebration of the region's rich culinary heritage.
Guest Experiences - Amidst the warmth of Lupaia's hospitality, guests are often surprised by thoughtful touches—like discovering little gifts awaiting them in their rooms, or the attentive staff who, without hesitation, offered to wash a delicate wedding gown, returning it impeccably cared for, all while sharing stories of the surrounding vineyards wafting sweet notes of ripe grapes through open windows.
Exceptional
159 reviews
Nestled in the enchanting hills of Montepulciano, Borgo San Vincenzo invites you to indulge in a luxurious escape bathed in Tuscan charm. With its stunning landscapes and serene gardens, this boutique haven is an intimate retreat where romance flourishes and every moment feels like a cherished memory.
Total Relaxation - Unwind in the sun-kissed outdoor swimming pool, surrounded by lush greenery and the gentle sounds of nature. Here, the air is perfumed with blooming flowers, offering a tranquil sanctuary to relish those lazy afternoons.
Romantic Getaways - Each elegantly appointed room boasts rustic charm mixed with modern comforts, inviting couples to linger over sunsets on private terraces while savoring a bottle of local wine. The ambiance is designed for shared moments, from candlelit dinners to starlit strolls through the picturesque grounds.
Cultural Explorations - With the vibrant history of Montepulciano at your doorstep, explore local vineyards and charming markets that burst with color and flavor. Immerse yourself in Tuscan culture as you discover ancient streets, artisanal shops, and stunning vistas that have inspired artists for centuries.
Guest Experiences - As guests sip their morning espresso, they revel in the rich aroma wafting from the kitchens, where homemade pastries whisper promises of indulgence. The warmth of the staff feels like family, each smile adding to the heartfelt experience, making it impossible not to feel at home among the rolling hills.
Exceptional
131 reviews
Nestled in the rolling hills of Montepulciano, Agriturismo Il Serraglio offers an enchanting escape where the simplicity of rustic charm meets modern luxury. Here, the scent of blooming gardens mingles with the warm Tuscan sun, creating a sanctuary for couples and wanderers alike, eager to savor life’s finer moments amidst breathtaking landscapes.
Romantic Retreat - Revel in intimate evenings by the outdoor fireplace, where the crackle of flames dances with laughter under a starlit sky, providing the perfect backdrop for unforgettable conversations.
Stunning Views - Awaken each day to panoramic vistas of lush vineyards and distant mountains; the infinity pool invites you to float while sipping a morning espresso, surrounded by nature's serene beauty.
Wellness Haven - Indulge in leisurely afternoons spent soaking in the hot tub, where the gentle whisper of the breeze through olive trees transforms relaxation into a sensory experience of pure bliss.
Guest Experiences - As you step outside with a cup of coffee, the crisp morning air greets you, while the distant sound of chirping birds fills the tranquil space—every moment feels imbued with a touch of magic, just as Alex, your attentive host, shares insider tips on hidden local gems that make every journey feel personal.
Exceptional
305 reviews
Nestled within the ancient walls of Cortona, Hotel Villa Marsili is a sumptuous retreat that elegantly marries history with modern luxury. Guests are enveloped in an atmosphere of romance and tranquility, where sweeping views of the Tuscan hills and the shimmering expanse of Lake Trasimeno create an inviting backdrop for unforgettable moments.
Total Relaxation - Indulge in the serene surroundings of our lush gardens, where fragrant blooms mingle with the gentle sounds of nature, inviting you to unwind as you sip afternoon tea or simply bask in the sun's warmth.
Historic Charm - Every corner of Villa Marsili whispers stories of centuries past, from the original frescoes that grace the walls to the elegant furnishings that reflect a bygone era, offering guests a chance to step into history while enjoying modern comforts.
Romantic Break - The enchanting ambiance, enhanced by cozy sitting rooms featuring crackling fireplaces, sets the perfect stage for intimate gatherings or silent moments shared over candlelit dinners, making every stay feel like a cherished love story.
Guest Experiences - Imagine waking up to the aroma of freshly brewed coffee mingling with homemade croque monsieurs wafting through the air, while the friendly staff greets you with genuine smiles, always ready to assist, whether it's parking your car or arranging a memorable pasta cooking class.
Exceptional
269 reviews
Nestled in the enchanting hills of Montepulciano, Agriturismo Merigge Wellness & Spa offers a harmonious blend of rustic charm and modern luxury. This idyllic retreat, surrounded by lush vineyards and olive groves, invites couples and wellness seekers alike to indulge in an atmosphere of tranquil elegance. With its infinity pool reflecting the Tuscan sky and a wellness spa designed for relaxation, each moment here feels like a gentle embrace from nature itself.
Total Relaxation - Unwind in the serene embrace of the spa, where soothing scents of essential oils mingle with the soft sounds of nature, creating an oasis of calm that rejuvenates both body and soul.
Romantic Break - Imagine sipping a glass of locally sourced wine on your private terrace as the sun sets, casting golden hues across the landscape—this is romance personified at Agriturismo Merigge, where every corner whispers love.
Culinary Delights - Begin your day with a delightful continental breakfast featuring freshly baked pastries and sun-ripened fruits, the aroma wrapping around you like a warm hug—a perfect prelude to exploring the culinary treasures of Tuscany.
Guest Experiences - As I stepped onto my balcony, the gentle breeze carried the sweet scent of blooming lavender, while the distant laughter of guests echoed softly through the garden, reminding me of the joy found in simple moments shared amidst breathtaking views.
Fabulous
13 reviews
Nestled within the sun-kissed hills of Tuscany, Villa San Sanino is a sanctuary of elegance and tranquility where luxury harmonizes with nature. As you step through the wrought iron gates, the scent of blooming lavender and rosemary wafts through the air, inviting you to unwind in this meticulously curated retreat adorned with exquisite architectural details and sprawling gardens.
Total relaxation - Embrace serenity at the villa's infinity pool, where shimmering waters seamlessly blend into the Tuscan skyline, offering a picturesque backdrop for lazy afternoons spent soaking up the sun or sipping on fine local wines.
Spa breaks - Indulge your senses in the spa, where the soft sounds of gentle chimes and the scent of essential oils create an atmosphere of deep relaxation, making it the perfect setting for rejuvenating treatments and tranquil yoga sessions amid stunning vistas.
Foodies - Savor a culinary journey at the on-site restaurant, where dishes crafted from locally-sourced ingredients tantalize the palate, enveloping you in fragrant aromas that mingle with the clinking of glasses and the laughter of fellow diners under the starry Tuscan sky.
Guest Experiences - One guest recalled the delightful surprise of discovering a hidden nook in the gardens, where they could enjoy morning coffee surrounded by the vibrant colors and sounds of nature—the chirping of birds providing a soothing soundtrack to their peaceful retreat.
Superb
221 reviews
Nestled in the enchanting hills of Chiusi, Poggio Piglia is a haven where rustic charm meets sophisticated luxury. The lush Tuscan landscape unfolds before your eyes, painting a picture of tranquil valleys and sprawling vineyards, inviting couples and adventurers alike to disconnect and immerse themselves in serene elegance.
Romantic Break - Whisk your beloved away to this idyllic retreat where secret garden pathways and intimate nooks inspire whispered conversations. As you savor candlelit dinners under a starry sky, the gentle clinking of glasses and soft melodies from a hidden guitar set the perfect backdrop for romance.
Total Relaxation - Unwind by the glistening infinity pool, where the panoramic views merge seamlessly with the horizon. Here, the scent of sun-warmed lavender fills the air, and the only sounds are the rustling leaves and soft chirps of nearby birds, creating a peaceful cocoon for those seeking solace.
Foodies - Indulge in culinary delights crafted from homegrown ingredients and local treasures, where each meal is a celebration of Tuscany's rich flavors. From freshly picked rocket leaves whisked into a delightful salad to the deep aromas of homemade dishes simmering nearby, every bite tells a story of care and tradition.
Guest Experiences - Imagine returning from a morning run to find a beautifully arranged table awaiting you, complete with a colorful salad and chilled wine, the owner grinning as they share their pride in the vibrant vegetable garden just steps away, a fragrant oasis of fresh herbs and ripe tomatoes.
Superb
105 reviews
Nestled among the rolling hills of Tuscany, Foresteria Il Giardino di Fontarronco is a sanctuary for lovers and explorers alike. Here, romance dances with nature in an enchanting embrace, offering secluded nooks to whisper sweet nothings while surrounded by the intoxicating scents of blossoming orchards and sun-drenched lavender fields.
Total Relaxation - Indulge in serenity as you lounge by the glistening pool, framed by lush gardens that sway gently in the warm Italian breeze. The atmosphere is imbued with a tranquil charm that invites you to unwind completely, leaving the world behind.
Local Exploring - With its ideal location just a whisper from historic towns like Florence and Siena, this charming retreat serves as your gateway to Tuscany's treasures. Wander through cobbled streets, savor artisanal delights at local markets, and immerse yourself in the rich tapestry of culture that lies just beyond your doorstep.
Foodies - Delight in mouthwatering meals at the on-site family-friendly restaurant, where each dish sings of seasonal ingredients and traditional recipes. The aroma of freshly baked cornetti wafts through the air each morning, beckoning guests to savor breakfast under the shade of ancient trees.
Guest Experiences - As dusk falls, the intimate glow of the outdoor barbecue area beckons, where laughter mingles with the crackling of the grill. Guests reminisce about evenings spent sharing stories over hearty meals, all while overlooking the serene landscape—a true taste of Italian hospitality wrapped in the warmth of home.
Exceptional
10 reviews
Nestled in the enchanting hills of Torrita di Siena, Siena House is a modern retreat where rustic charm meets luxury. With sweeping views of the verdant landscape, this idyllic haven invites couples and adventurous souls alike to unwind in serene tranquility, whether lounging by the shimmering pool or savoring exquisite homemade breakfasts that celebrate the region's bountiful flavors.
Total Relaxation - Every corner of Siena House exudes calm, from the soothing sounds of nature that lull you to sleep to the sun-drenched terrace where you can sip your morning coffee while soaking in breathtaking vistas. It's a true escape into peace.
Romantic Break - With its intimate ambiance and charming decor adorned with local artworks, Siena House provides the perfect backdrop for love stories to flourish. Imagine cozy evenings under starlit skies, complemented by the warm glow of laughter and shared memories.
Spa Breaks - Indulge in wellness at Siena House, where the gentle whispers of the garden enhance your relaxation. Enjoy refreshing dips in the outdoor pool, juxtaposed with pampering amenities like plush towels and thoughtful touches that make every moment feel special.
Guest Experiences - Guests often reminisce about the delightful breakfast spread featuring fresh duck and geese eggs, paired with homemade Greek yogurt that dances on their taste buds. The warmth of hosts Malvin and Amanda shines through as they share personal touches, like teaching visitors how to create their own yogurt, making each visit feel like coming home.
Exceptional
71 reviews
Nestled in the picturesque landscape of Bettolle, Relais la Leopoldina is a hidden gem where romance and serenity intertwine. The elegant retreat invites couples and solo travelers alike to indulge in an atmosphere of sophisticated charm, surrounded by lush gardens and stunning vistas that whisper tales of Tuscany's timeless allure.
Total Relaxation - Savor lazy afternoons beside the sparkling seasonal pool, where the gentle sound of water dances with the rustle of fragrant olive trees, enveloping you in tranquility and bliss.
Culinary Delights - Experience an unforgettable dining journey at the hotel's exquisite restaurant, where locally sourced ingredients transform each meal into a celebration of Italian flavors, served with warmth—a perfect way to unwind after a day of exploration.
Chic Comfort - Retreat to your air-conditioned sanctuary, where every detail has been thoughtfully curated—plush bedding, modern amenities, and captivating views ensure a peaceful night's sleep amidst the enchanting Tuscan nights.
Guest Experiences - Each morning unfolds with the rich aroma of freshly brewed Italian coffee wafting through the air, as friendly staff members recall how you like it. Guests have relished those small yet personal touches, from the comforting warmth of hot water for tea before bed to the delightfully clean pool beckoning them for a refreshing dip.
Superb
80 reviews
Nestled among the rolling hills of Le Piazze, La Fontaiola is a hidden gem where rustic charm meets modern luxury. Here, the air is infused with the sweet scent of wildflowers and freshly baked bread, creating an enchanting backdrop for couples and solo travelers seeking solace or adventure alike. With its intimate gardens and stunning mountain views, every corner of this exquisite farm stay whispers romance and relaxation.
Romantic Retreat - La Fontaiola provides the perfect setting for romance to blossom, with private accommodations that exude warmth and allure. Guests can bask in the sun near the shimmering pool or unwind under the stars, surrounded by the serene sounds of nature.
Total Relaxation - Immerse yourself in tranquility as you stroll through lush gardens, dive into refreshing waters, or simply savor the gentle rustle of leaves in the breeze. This haven is designed for those yearning for peace and rejuvenation, away from life's bustling demands.
Culinary Delights - Awaken your senses each morning with an Italian breakfast featuring freshly baked pastries and rich coffee, lovingly prepared by attentive hosts. The aroma of warm bread wafting through the air sets the stage for a day filled with exploration and local flavors.
Guest Experiences - One guest recalled the delightful surprise of fresh bread delivered daily, filling the air with comforting scents as they enjoyed their morning coffee on the terrace. The friendly banter with the hosts, who went above and beyond to ensure every need was met, turned their stay into an unforgettable experience steeped in hospitality.
Superb
378 reviews
Nestled amidst the rolling hills of Tuscany, Villa di Piazzano beckons couples and discerning travelers to a realm of tranquility and romance. This exquisite family-run villa, with its opulent antique furnishings and breathtaking vistas, offers an enchanting escape where time stands still and every moment whispers luxury.
Romantic Getaway - With enchanting gardens that bloom with vibrant colors and the gentle rustle of leaves in the breeze, this sanctuary invites lovers to stroll hand-in-hand along sun-dappled pathways, culminating in intimate dinners under a starlit sky on the terrace.
Culinary Delights - Indulge in Tuscan cuisine that tantalizes the senses at L'Antica Casina di Caccia, where each dish is crafted from local harvests, transforming simple ingredients into gastronomic masterpieces savored against the backdrop of picturesque countryside views.
Serene Escape - The harmonious balance of elegance and comfort permeates the air, as guests unwind by the poolside, enveloped by lush greenery while the soft sounds of chirping birds create a serene soundtrack to their peaceful retreat.
Guest Experiences - Upon arrival, the warm welcome was marked by the effervescent pop of Prosecco being poured, instantly setting a celebratory tone. Guests often mention the blissful sensation of slipping between the crisp, luxurious sheets, drifting off to the distant sound of laughter and clinking glasses echoing through the garden.
Exceptional
28 reviews
Nestled in the heart of the enchanting Tuscan countryside, Fontelunga Hotel & Villas invites you to indulge in an intimate escape where time slows and beauty flourishes. With sprawling gardens that cradle a shimmering pool and charming tennis courts, this retreat envelops you in luxury while offering a serene backdrop for romance and relaxation, creating an atmosphere that's as inviting as it is sophisticated.
Total Relaxation - Unwind beneath the warm Tuscan sun, where every corner of the hotel radiates tranquility; the outdoor pool sparkles enticingly, inviting you to bask in its cool embrace amidst fragrant blooms and whispering leaves.
Romantic Break - Each elegantly designed room boasts breathtaking valley views, perfect for sharing magical moments with your loved one as the golden sun sets, painting the sky in hues of orange and pink—an idyllic canvas for romance.
Culinary Delight - Savor the essence of Italy with dishes crafted from local ingredients at the on-site restaurant, where the tantalizing aroma of freshly prepared cuisine wafts through the air, setting the stage for culinary adventures enhanced by optional cooking classes led by a passionate private chef.
Guest Experiences - Guests often find themselves entranced by the gentle sounds of laughter echoing from the garden during breakfast, where the smell of freshly brewed coffee mingles with the sweetness of ripe figs, creating an atmosphere that feels like home—a place where connections flourish amidst stunning scenery.
Superb
201 reviews
Nestled amidst the sun-kissed olive groves and vineyards of the enchanting Val di Chiana, I Grandi Di Toscana exudes a tranquil charm that beckons romantic souls seeking an idyllic retreat. This restored Tuscan farm estate offers a luxurious sanctuary where traditional elegance meets modern sophistication, enveloped by breathtaking views of rolling hills and distant Cortona.
Total Relaxation - Immerse yourself in serenity as you unwind by the shimmering pool or stroll along private walking trails that wind through lush landscapes. The gentle sounds of rustling leaves and distant birds create an atmosphere perfect for peaceful reflection.
Romantic Break - Indulge in intimate moments with your partner while savoring exquisite local cuisine under a starlit sky. From candlelit dinners to quiet afternoons in beautifully refurbished suites, every detail is designed to cultivate romance.
Outstanding Location - Perched on a hillside that reveals panoramic vistas, the property invites exploration of nearby charming towns and the rich tapestry of Tuscan culture. Each day unveils a new adventure, from delightful wine tastings to leisurely tennis matches against the backdrop of stunning countryside.
Guest Experiences - Guests have marveled at the extensive breakfast spread, where the aroma of freshly brewed cappuccinos mingles with the sweet scent of pastries, creating a morning symphony of flavors. A delightful dinner featuring succulent steak paired with local pasta left one couple reminiscing about their meal, which was punctuated by warm, attentive service that felt like a family gathering.
Superb
402 reviews
Nestled among the rolling hills of Montepulciano, Villa Svetoni Wine Resort is a luxurious retreat where rustic charm meets modern elegance. Here, the air is infused with the earthy scent of nearby vineyards and wildflowers, promising a serene escape for couples seeking romance or travelers in search of adventure.
Romantic Escape - The secluded terraces offer intimate spots to savor breathtaking sunsets, while the whisper of leaves rustling in the gentle breeze creates an enchanting backdrop for stolen moments.
Culinary Delights - Savor exquisite flavors at the on-site Michelin-star restaurant, where every dish is a masterpiece crafted from local ingredients, followed by a glass of robust wine from the estate that dances on your palate.
Wellness Retreat - Unwind by the shimmering seasonal pool, enveloped in the tranquility of meticulously landscaped gardens, as the soothing sounds of nature invite you to let go and rejuvenate.
Guest Experiences - One guest marveled at the vibrant colors of the sunset reflecting off the water, sharing that the friendly staff even arranged a last-minute candlelit dinner when they mentioned celebrating a special occasion, adding a personal touch that made their stay unforgettable.
Superb
222 reviews
Nestled within 15 acres of lush Tuscan countryside, Villa Poggiano is a sanctuary of tranquility and romance, where the soft melodies of nature harmonize with stunning vistas. This family-run estate enchants its guests with a warm embrace, luxurious accommodations, and an enchanting marble pool that invites you to linger under the Italian sun, creating unforgettable moments amidst the hills of Val d’Orcia.
Romantic Escape - Designed as a love letter to intimacy, Villa Poggiano offers elegantly decorated suites that boast breathtaking views of rolling olive groves and golden cornfields, perfect for couples seeking solace and connection in the heart of Tuscany.
Total Relaxation - Indulge in leisurely mornings with a delightful breakfast spread featuring freshly baked pastries, local meats, and artisanal cheeses, all enjoyed while soaking in panoramic views that stretch across the idyllic landscape until late morning.
Local Exploring - A mere five-minute drive leads you to the medieval charm of Montepulciano, where cobblestone streets beckon discovery, with the friendly staff on hand to curate memorable excursions, from vineyard tours steeped in tradition to culinary classes that celebrate the flavors of the region.
Guest Experiences - As the sun dipped below the horizon, guests found joy on their Juliet balconies, savoring the rich aroma of local wines while the soft chirping of crickets serenaded them, offering a blissful backdrop to evenings spent reminiscing about their adventures that day.
Superb
670 reviews
Nestled in the heart of Montepulciano, Il Rondò Boutique Hotel invites you to escape into a world where 18th-century Tuscan charm meets modern luxury. With its lush gardens and intimate ambiance, this enchanting retreat offers couples and travelers alike a serene sanctuary, just a short stroll from the vibrant historic center.
Romantic Retreat - Whisper sweet nothings amidst beautifully decorated rooms adorned with antique furniture, where the air is infused with the scent of blossoming fig and olive trees, creating an idyllic setting for lovebirds.
Culinary Delights - Start your day with a delectable buffet breakfast featuring local products, served al fresco in the garden, as the gentle rustling of leaves and chirping birds serenade you, making every morning feel like a dreamy escape.
Exquisite Gardens - Step into a captivating oasis where bistro tables invite you to enjoy breathtaking views, framed by vibrant flowers and the soothing sounds of nature, perfect for savoring a glass of Montepulciano wine under the Tuscan sun.
Guest Experiences - One guest recalled the delightful surprise of enjoying figs straight from the garden, their sweetness complemented by the warmth of the hosts who shared heartfelt recommendations, making each moment feel personal and cherished.
Superb
431 reviews
Nestled amidst the rolling hills of Montepulciano, Villa Cicolina exudes an enchanting blend of antiquity and charm. This historic retreat, once the summer haven of a noble family, invites you to unwind in its lush gardens and bask in breathtaking views of the idyllic Tuscan landscape, where every corner whispers stories of the past.
Romantic Escape - With its candlelit dinners under a starlit sky and intimate corners adorned with exquisite frescoes, Villa Cicolina is a sanctuary for lovers seeking a timeless romance amidst the beauty of Tuscany.
Total Relaxation - Soak in the serene ambiance while lounging by the hydro-massage pool surrounded by fragrant olive groves, where the gentle sound of rustling leaves and distant birds creates a perfect backdrop for peace and tranquility.
Culinary Delight - Savor the essence of Tuscany at the on-site restaurant, where each dish celebrates local produce and traditional flavors, making every meal a delightful exploration of regional cuisine that guests eagerly return for night after night.
Guest Experiences - Awake to the aroma of freshly baked pastries wafting through your window, a reminder of the abundant breakfast spread waiting just outside. As you step into the sun-drenched courtyard, the vibrant colors of blooming flowers and the soft chatter of fellow travelers create a welcoming symphony, inviting you to linger just a moment longer.
Superb
519 reviews
Nestled within the ancient stone walls of a beautifully restored monastery, Monastero di Cortona Hotel & Spa exudes a sense of serene luxury and romance. As sunlight dances through the stained glass, you’ll find yourself embraced by an atmosphere of tranquility, where every detail whispers tales of history against the backdrop of rolling Tuscan hills.
Romantic Break - Enjoy intimate moments on your private balcony, where the scent of blooming jasmine mingles with the soft sound of rustling leaves, while you gaze upon the enchanting vistas of Cortona’s charming village.
Spa Breaks - Indulge in personalized wellness experiences at our luxurious spa, where each treatment is tailored to rejuvenate your spirit, accompanied by soothing sounds and the subtle aroma of essential oils that envelop you in pure relaxation.
Total Relaxation - Relax by the pool, sipping a refreshing cocktail as you soak in breathtaking views; the gentle lapping of water and the sun's warm embrace create a perfect escape from everyday life.
Guest Experiences - Guests often reminisce about the delightful breakfast served on the terrace, where the aroma of freshly brewed coffee and pastries wafts through the air, accentuated by the friendly staff who greet you with warm smiles and small treats that feel like home.
Superb
737 reviews
Perched amidst the rolling hills of Tuscany, Villa Schiatti is a romantic sanctuary where time slows and tranquility reigns. As you step into this historic villa, the aroma of freshly baked pastries wafts through the air, welcoming you to indulge in the rich flavors of Italian cuisine, all while basking in panoramic views that stretch across the vibrant valleys below.
Romantic Retreat - Nestled within beautifully landscaped gardens, the outdoor pool invites couples to unwind under the Tuscan sun, while evenings come alive with candlelit dinners on the terrace—each sunset painting a breathtaking backdrop for your intimate moments.
Culinary Delights - Savor the heart of Tuscany at the on-site restaurant, offering a delightful blend of traditional Tuscan specialties and classic Italian fare, with each dish prepared using locally sourced ingredients that tantalize the taste buds and create a feast for the senses.
Outdoor Adventures - Venture beyond the villa's serene confines to explore winding trails perfect for hiking or mountain biking, as the surrounding hills beckon adventure seekers to immerse themselves in nature’s splendor, culminating in wine tasting tours that uncover the region's hidden gems.
Guest Experiences - Guests often find themselves captivated by the inviting ambiance of the communal balcony, a cherished spot adorned with plush seating where laughter mingles with the soft sounds of nature—the perfect place to sip a glass of Chianti while enjoying the gentle breeze.
Superb
263 reviews
Nestled amidst the enchanting hills of Cortona, Locanda agli Amici is a sanctuary for romance and relaxation, where every moment feels like a private escape. The allure of luxury intertwines seamlessly with the warm embrace of Italian hospitality, inviting couples and adventure seekers alike to unwind in its elegantly appointed spaces, all while basking in breathtaking views that stretch across the picturesque landscape.
Romantic Break - Every corner of Locanda agli Amici exudes intimacy, from the serene garden where lovers can linger over a glass of wine to the charming terrace that offers sunsets painted in vibrant hues—a true haven for those seeking a romantic getaway.
Total Relaxation - The seasonal outdoor swimming pool beckons with crystal-clear waters, surrounded by lush greenery—an idyllic spot for delightful afternoons spent lounging under the sun, punctuated by gentle breezes and the distant sound of cicadas as you sip on refreshing cocktails.
Culinary Delights - Savor the authentic flavors of Italy at the on-site restaurant, where each meal is crafted with fresh, local ingredients—guests rave about the extraordinary breakfast spread, featuring everything from rich pastries to made-to-order egg dishes, all complemented by stunning views that enhance every bite.
Guest Experiences - Imagine waking up to an aromatic blend of freshly brewed coffee and the sweet scent of pastries wafting through your open window, only to discover that the friendly staff has arranged a specially packed breakfast for your early departure, ensuring you leave with delicious memories in tow.
Superb
468 reviews
Nestled within the embrace of rolling hills and ancient vineyards, LaChiusa Tuscany offers a serene escape into the heart of the Tuscan countryside. Housed in a lovingly restored oil mill, this enchanting retreat exudes rustic charm and elegance, with stone walls whispering tales of history and gardens that entice you to linger among their fragrant blooms.
Panoramic Gardens - Step outside to discover lush gardens adorned with sun loungers, where breathtaking views of the Montepulciano landscape stretch endlessly before you. The gentle rustle of leaves and distant sounds of nature create a tranquil backdrop for unwinding under the Tuscan sun.
Culinary Delights - Indulge in an exquisite dining experience at the on-site restaurant, where the aroma of freshly prepared local specialties mingles with fine wines from nearby vineyards. With charming arched brick walls and a welcoming ambiance, every meal becomes a celebration of Tuscany's rich culinary heritage.
Romantic Retreat - Spacious rooms echo the allure of Tuscany with wood-beamed ceilings and rustic décor, offering intimate hideaways enhanced by stunning garden views. Each moment spent here feels like a romantic interlude, perfect for couples seeking both adventure and relaxation amid the picturesque scenery.
Guest Experiences - Imagine waking to the soft light filtering through your window, the scent of fresh pastries wafting from the breakfast terrace—where guests rave about the delightful spread enjoyed with panoramic views. One visitor spoke of finding peace in the massive jacuzzi, surrounded by medieval-like design, evoking fairy-tale tranquility in every bubble.
Superb
278 reviews
Tucked away in the sun-drenched hills of Cortona, Agriturismo I Pagliai invites you to experience an enchanting blend of rustic charm and modern comfort. Here, the aroma of freshly baked focaccia wafts through sunlit rooms, while gentle breezes rustle the leaves of sprawling trees. This romantic retreat offers a serene escape, where every moment is infused with the essence of Tuscany's breathtaking landscapes.
Total Relaxation - Unwind beside the sparkling outdoor pool, where the rhythmic sound of nature embraces you. With shaded lounging areas and vibrant gardens surrounding you, it's an idyllic spot for intimate moments or leisurely afternoons soaked in tranquility.
Romantic Break - Experience cozy evenings under a star-studded sky, as you sip on local wines and share tales of adventure with your loved one. The warmth of flickering candles and the soft glow from the nearby terrace create an intimate atmosphere that lingers in your memory long after your stay.
Local Exploring - Discover the hidden gems of Cortona and its picturesque surroundings during leisurely strolls through charming streets. Engage in delightful conversations with friendly locals at nearby markets, where the vibrant colors of fresh produce beckon with the promise of culinary delights.
Guest Experiences - Guests have cherished the warm embrace of the agriturismo, noting how the scent of homemade breakfast fills the air each morning, enticing them to the dining area. There's something comforting about sinking into plush bedding after a day spent exploring, knowing that the laughter of smiling staff and the delicious taste of home-cooked meals will greet them again tomorrow.
Guest Review: Chose this hotel outside Cortona for its views and pool and neither disappointed. The grounds and pool are beautifully kept, and plenty of seating/sunbeds with shade if you want it (I do!). Dinner on the terraced outdoor restaurant was also accompanied by a fab sunset over the valley. Room had character, was clean, and with quiet aircon. Breakfast was a veritable feast if you wanted it, and the variety, even for those of us wanting savoury options, was excellent. The location was only a 10-minute drive from Cortona, which had ample parking.
Guest Review: I loved it, I certainly will be back. It was quaint..The host were extraordinary. Very kind and thoughtful.
Guest Review: I do not know where to begin! 😀 The hotel, surroundings and the location 10/10! The staff is very firendly, kind and always smiling so the atmosphere is very nice! They were very helpful with my gluten free diet (I am coeliac) and they gave us a great recommendations for Cortona attractions 😀 The balcony with the pool is divine with a spectacular view of the village. Breakfast at the balcony is a five star experience 😀
Guest Review: It’s a beautiful estate in the country side surrounded by amazing nature. The house is spacious and has all the things you need. The host are super nice and informative.
Guest Review: We visited for 4 days March 24-28. Unfortunately it rained 60% of the time we were there which has an influence on this review. First, the property is gorgeous! Exceeded my expectations! The food was amazing. The staff went above and beyond to meet my dietary restrictions (gf, df). Thank you Lavenia! Thoroughly enjoyed the hot tub. We did the wine tasting with Anita which was awesome! Also enjoyed the organized dinner with Anita.
For an entertaining stay in Val di Chiana, consider Agriturismo Merigge Wellness & Spa Montepulciano for its wellness and spa facilities or Borgo San Vincenzo, known for its lively atmosphere and events. Both provide unique experiences that blend relaxation with fun.
Yes! Families can enjoy a delightful stay at Podere Le Volte Country House La Mita, which offers spacious accommodations and outdoor activities, or Agriturismo Il Serraglio, perfect for kids with its farm setting and engaging experiences.
Indulge in luxury at Villa di Piazzano - Small Luxury Hotels of the World, where opulence meets stunning views, or Hotel Villa Marsili, known for its elegant interiors and exceptional service, making them ideal choices for a lavish getaway.
For a romantic escape, Lupaia offers enchanting landscapes and intimate settings, while Foresteria Il Giardino di Fontarronco boasts cozy accommodations surrounded by nature, perfect for couples seeking tranquility and connection.
Travelers on a budget can opt for La Fontaiola, which provides charming rooms at great prices, or Siena House, offering a delightful experience without breaking the bank, ensuring comfort and affordability.
For visually stunning stays, check out Fontelunga Hotel & Villas known for its contemporary design and breathtaking views, or Poggio Piglia, celebrated for its stylish interiors and artistic vibe, both perfect for design enthusiasts.