The 19 Best Boutique Family Hotels in Cortona Countryside (2025)

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.

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.

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.

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.

Nestled among the verdant hills of Cortona, Villa Borgo San Pietro is a sanctuary of romance and tranquility, where ancient stone walls whisper tales of history under the Tuscan sun. This exquisite historic farmhouse invites you to indulge in luxurious surroundings, complete with an enchanting outdoor pool that mirrors the azure skies above, creating a private oasis for couples and wanderers alike.

Romantic Break - Savor intimate moments as you explore the lush gardens, stroll past the ancient well, or unwind by the serene pool, all while surrounded by breathtaking views of the picturesque landscape, perfect for rekindling passion or celebrating love.

Total Relaxation - Experience pure bliss as you sink into plush bedding, embracing the charm of beamed ceilings and terracotta floors, while the gentle rustle of leaves outside lulls you into a state of deep relaxation and peace.

Local Exploring - With Cortona just a short drive away, embark on adventures through charming cobblestone streets, indulging in local markets and eateries that tantalize your taste buds with authentic Tuscan flavors and inviting aromas.

Guest Experiences - Upon arrival, guests are greeted not only with a glass of wine but also by the warm smiles of staff members who go above and beyond, like Alessandro, whose thoughtful recommendations help travelers uncover hidden gems, making each visit feel like coming home.

Nestled in the tranquil hills of Cortona, Monastero San Silvestro invites you to retreat into a world where history meets modern elegance. This former monastery, steeped in tradition, offers a sanctuary of romance and relaxation, enveloped by breathtaking countryside vistas and the soothing sounds of nature.

Romantic Getaway - Discover intimate corners perfect for lovers—enjoy a glass of local wine on your private terrace as the sun sets over rolling green hills, painting the sky with hues of pink and gold.

Total Relaxation - Unwind in our saltwater pool, surrounded by lush gardens filled with fragrant herbs. Join a calming yoga class at dawn, where the gentle rustle of leaves creates an idyllic backdrop for meditation.

Local Exploring - Venture just a short drive to Cortona’s charming streets, where cobblestone pathways lead you to bustling markets and delightful restaurants, allowing you to immerse yourself in the rich Tuscan culture.

Guest Experiences - As you step into your spacious apartment, the rustic charm captures your heart—the scent of aged wood mixes with fresh pastries from breakfast, while the soft chatter of nearby horses fills the air, reminding you that this serene escape is as much about comfort as it is about connection to nature.

Nestled in the serene embrace of Tuscany’s rolling hills, Relais Villa Baldelli is a 17th-century villa that invites you to indulge in timeless luxury amidst nature's splendor. With its elegant blend of vintage décor and modern comforts, this hidden gem promises an intimate escape where romance flourishes and tranquility reigns supreme.

Romantic Getaway - Cocoon yourself in an atmosphere of love, as soft whispers of the countryside serenade your evenings on the terrace, with twinkling stars above creating the perfect backdrop for unforgettable moments.

Historic Charm - Wander through the villa's enchanting halls adorned with period decorations, where echoes of history mingle with the scent of blooming flowers from the gardens, enveloping you in a unique sense of time and place.

Total Relaxation - Take a dip in the fabulous outdoor pool, framed by lush greenery; the gentle sound of water cascading nearby creates a soothing soundtrack while you bask in the sun or unwind with a book on a plush lounge chair.

Guest Experiences - One evening, as the sun set over the hills, the cozy warmth of the antique fireplace filled the breakfast room, where guests shared laughter and stories, making friends who would reminisce about their travels long after the holiday ended.

Nestled in the heart of Tuscany, Il Falconiere Relais & Spa exudes an exquisite blend of elegance and warmth, inviting couples and luxury seekers to experience a romantic retreat amidst rolling vineyards and age-old olive groves. The air is imbued with the scent of fresh herbs and blooming flowers, setting the stage for unforgettable moments in this enchanting 17th-century manor just outside Cortona.

Total Relaxation - Unwind in the serene embrace of the Thesan Etruscan Spa, where soothing aromas mingle with soft music as you indulge in sensory showers, luxurious massages, and rejuvenating treatments designed to refresh your spirit and pamper your senses.

Culinary Delights - Savor traditional Tuscan cuisine in a converted orangery, the Michelin-starred restaurant offering seasonal dishes crafted from local ingredients, each bite bursting with flavors that whisk you away on a culinary adventure paired with the estate's own Baracchi wines.

Scenic Escape - Bask in the breathtaking views of the surrounding hills while lounging by the outdoor pool, where sun-drenched days melt into starlit evenings, surrounded by the whispered rustle of leaves and the tranquil sounds of nature, creating a private sanctuary for relaxation and reflection.

Guest Experiences - Imagine waking up to the gentle sound of chirping birds and slipping into a beautifully designed room where the decor speaks to the rich history of the manor. Guests have cherished the delightful breakfast ambiance, often sharing stories of the charming staff who make every morning feel like a special occasion, accompanied by the enticing aroma of freshly brewed coffee wafting through the air.

Nestled in the heart of Cortona, Italy, Relais La Corte dei Papi is a luxurious haven where elegance meets the enchanting charm of Tuscany. With its meticulously manicured gardens and the soothing sounds of nature, this oasis offers an intimate escape for couples and wellness seekers alike, wrapped in the warmth of Italian hospitality.

Romantic Retreat - Each room is a sanctuary of serenity, adorned with soft linens and delicate artwork, inviting you to unwind on your private patio while sipping a local Chianti as the sun sets behind rolling hills.

Wellbeing Sanctuary - Indulge in rejuvenating treatments at the spa or relax in the hot tub under a starlit sky, where every moment is designed to elevate your sense of peace and comfort amidst breathtaking surroundings.

Culinary Delights - Savor an array of exquisite dishes crafted from fresh, local ingredients in the hotel's restaurant, where each bite tells a story of Tuscan tradition and innovation, complemented by attentive service that makes every meal a special occasion.

Guest Experiences - As you stroll through the lush gardens, the scent of blooming jasmine fills the air, while the owner David's genuine laughter resonates warmly, making you feel like part of the family—just before you retreat to your room where the soft glow of candles creates an ambiance of tranquil romance.

Nestled in the charming town of Foiano della Chiana, Boutique Hotel L'Imperatrice radiates an air of modern elegance infused with local character. With its chic décor and inviting atmosphere, guests are enveloped in a serene embrace, where every corner invites romance and rejuvenation amidst the stunning Tuscan landscape.

Romantic Break - Set against a backdrop of rolling hills, indulge in intimate evenings on the terrace as you sip local wines and bask in the golden hues of sunset, creating cherished memories that linger long after your stay.

Total relaxation - Rejuvenate your senses in thoughtfully designed rooms adorned with local artworks, where the soft rustle of the breeze through the windows harmonizes with the subtle aroma of fresh coffee brewing nearby—an experience for both the body and soul.

Cultural explorers - With a plethora of nearby historic gems waiting to be discovered, embark on a journey through time as you wander cobblestone streets, savoring the rich tapestry of art and tradition that defines this enchanting region.

Guest Experiences - Morning at L'Imperatrice begins with a warm greeting from your hosts, their laughter mingling with the scent of freshly baked pastries wafting through the halls—each breakfast feels like a lovingly prepared family gathering, setting the perfect tone for the day.

Nestled amidst the rolling hills of Tuscany, Villa Vignacce - Boutique Country Resort is a serene escape where luxury meets rustic charm. With stunning views and meticulously tended gardens, this boutique resort invites couples and travelers alike to unwind in an oasis of tranquility, enveloped by the gentle sounds of nature and the warm embrace of Italian hospitality.

Romantic Getaway - The intimate ambiance of Villa Vignacce sets the stage for love; guests are often seen savoring quiet moments together under the shade of olive trees or sharing sunset strolls through fragrant gardens, making it the perfect backdrop for romantic memories.

Boutique Charm - Each room tells its own story with antique furnishings and unique decor, offering a cozy yet chic retreat. Guests relish the tactile experience of high-quality linens and the aroma of fresh Mediterranean herbs wafting through the air during leisurely breakfasts on their private terraces.

Total Relaxation - Soak in the sun by the inviting pool, elegantly framed by lush greenery and blooming flowers, where laughter mingles with the soft splashes of water. The gentle hum of cicadas creates a peaceful soundtrack as you recline on plush loungers, cocktail in hand, savoring the slow pace of Tuscan life.

Guest Experiences - One guest fondly recalls the delightful surprise of finding a hidden nook in the garden, where they could sip wine and listen to the rustling leaves, while another described Anna's warm welcome that felt like reuniting with an old friend, as she effortlessly catered to their every need with genuine enthusiasm.

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.

Nestled in the serene embrace of Tuscany's rolling hills, Agriturismo Podere La Rocca is a romantic retreat where time slows down and every detail exudes charm. As you step into this beautifully restored 18th-century mansion, the warmth of rustic elegance envelops you, inviting you to indulge in luxurious comfort amidst nature's breathtaking tapestry.

Romantic Break - With enchanting views of lush vineyards and golden sunsets, each moment at Agriturismo Podere La Rocca feels like a scene from a love story, perfect for couples seeking an intimate escape.

Total Relaxation - The tranquil gardens, punctuated by the gentle sounds of chirping birds and rustling leaves, are ideal for lounging by the sparkling pool, creating a peaceful sanctuary for wellness enthusiasts and relaxation seekers alike.

Culinary Delights - Savor the essence of Tuscany at the on-site restaurant, where the aroma of freshly prepared dishes fills the air, mingling with laughter and conversation as guests share in the joy of exquisite local flavors.

Guest Experiences - Imagine waking up to soft sunlight filtering through your window, accompanied by the enticing scent of homemade pastries wafting from the kitchen. Guests often reminisce about how the caring staff would go out of their way to provide personalized recommendations, turning simple meals into cherished memories shared over candlelit dinners.

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.

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.

Nestled in the enchanting landscape of Bettolle, Albergo La Foresteria invites guests to indulge in a serene escape where modern comforts meet rustic charm. With its lush gardens and inviting terraces, this boutique hotel creates an intimate atmosphere, perfect for romantic getaways or tranquil retreats amidst the rolling hills of Tuscany.

Culinary Delights - Savor the essence of Italy as you wake up to a sumptuous breakfast featuring freshly brewed espresso and a tantalizing selection of homemade pastries that waft their sweet aroma through the air, crafted by talented chefs who pour their heart into every dish.

Idyllic Location - Surrounded by breathtaking vistas, Albergo La Foresteria offers easy access to local markets and historical treasures, making it a haven for cultural explorers eager to uncover the rich tapestry of Tuscan heritage just a short ride away.

Personalized Service - The attentive staff at this charming hotel ensure your stay is nothing short of exceptional, greeting you with genuine warmth and seamlessly accommodating your every need, creating a friendly ambiance that feels like visiting cherished friends.

Guest Experiences - As you sip your morning coffee on the terrace, the soft chirping of birds fills the air, a reminder that tranquility reigns here. Guests fondly recall evenings spent chatting with the owners, whose delightful anecdotes about the region add a personal touch to the experience.

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.

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.

Nestled atop a serene hill in Montepulciano, Precise Tale Poggio Alla Sala is where elegance meets tranquility. With panoramic views of the Tuscan landscape, each moment here feels like a scene from a romantic film, offering couples and luxury seekers an enchanting retreat to unwind and reconnect.

Total Relaxation - Indulge in a sanctuary designed for rejuvenation, where a state-of-the-art spa beckons with soothing treatments and serene relaxation spaces, while the indoor pool and sauna invite you to escape into pure bliss.

Romantic Break - Imagine savoring exquisite cuisine under the stars on the terrace, where every bite tells the story of local flavors, complemented by the soft sounds of nature that enhance your evening escape.

Outstanding Location - Situated just moments away from charming vineyards and historic towns, this hotel offers an irresistible blend of adventure and exploration, perfect for cultural explorers eager to immerse themselves in Tuscany's rich heritage.

Guest Experiences - As you step into the lobby, the warm scents of mulled wine envelop you, instantly making you feel at home. A leisurely morning unfolds as you indulge in a buffet breakfast, where the array of artisanal cheeses tempts you to linger longer, savoring each taste while gazing out at the breathtaking valley view.