The 12 Best Boutique Hotels with Entertainment in Windsor (2025)

Nestled in the heart of Eton's historic High Street, The Christopher Hotel exudes a timeless charm that marries its rich 16th-century heritage with contemporary elegance. Picture yourself unwinding in your beautifully appointed room, where every detail is designed for comfort and sophistication, making it the perfect romantic getaway or serene retreat for cultured explorers.

Romantic Break - With its enchanting ambiance and intimate settings, The Christopher Hotel is the ideal backdrop for love stories to blossom, whether you’re savoring a candlelit dinner or enjoying quiet moments on the sun-kissed deck.

Outstanding Location - Located just steps from Windsor's iconic sights, guests can lose themselves in local markets, historical landmarks, and blooming gardens, all within a leisurely stroll down the picturesque streets filled with character.

Total Relaxation - Indulge in blissful tranquility as you sink into luxurious Hypnos beds, complemented by complimentary treats that awaken your senses. The delightful aroma of freshly brewed coffee mingles with warm pastries at breakfast, promising a perfect start to your day.

Guest Experiences - Arriving to an upgraded suite adorned with chocolates and a personalized card, one couple found their anniversary weekend transformed into an unforgettable escape, with the friendly staff always ready with a warm smile and a welcome drink to elevate their stay.

Nestled in the picturesque village of Winkfield, The Winning Post is an enchanting retreat that effortlessly marries modern elegance with rustic charm. With its inviting atmosphere and meticulously restored 18th-century features, this boutique inn beckons couples and travelers alike to unwind amidst lush garden terraces and intimate nooks, all just a stone's throw from the historic splendor of Windsor.

Romantic Escape - Whisk away your loved one to a haven designed for romance, where candlelit dinners showcase locally sourced delicacies and whispering breezes invite moonlit strolls through the gardens.

Total Relaxation - Indulge in the serene ambiance enhanced by thoughtfully refurbished rooms, each adorned with plush furnishings, while the gentle hum of nature outside lulls you into blissful tranquility.

Culinary Delight - Savor an exquisite culinary journey with dishes crafted from fresh local produce; revel in the delightful aromas wafting from the kitchen as you enjoy a warm, inviting meal paired with a curated selection of fine wines and seasonal cocktails.

Guest Experiences - Guests have relished the cozy pub feel, often lingering over a fantastic Bloody Mary as laughter mingles with the clinking of glasses, while others have cherished the personalized warmth from the staff, who go above and beyond to ensure every detail enhances their stay.

Nestled in the heart of Royal Windsor, overlooking the majestic Windsor Castle, Macdonald Windsor is an exquisite blend of modern luxury and historic charm. With its romantic ambiance and boutique flair, this hotel invites couples and travelers alike to indulge in a sanctuary of comfort, where every detail whispers elegance and every moment feels extraordinary.

Outstanding Location - Step outside and feel the pulse of history as Windsor Castle beckons from across the street, creating an enchanting backdrop for your stay. The vibrant energy of the High Street invites exploration, with the delightful sounds of the Changing of the Guard echoing through the air on weekends.

Romantic Retreat - With individually styled rooms that exude warmth and intimacy, each corner of Macdonald Windsor offers a perfect setting for romance. Plush bedding, soft textures, and thoughtful details like bathrobes and slippers create an inviting atmosphere, ideal for lovebirds seeking a tranquil escape.

Culinary Delight - Savor the flavors of Caleys Restaurant, where a menu crafted from seasonal and organic produce tantalizes your palate. The aroma of freshly brewed coffee mingles with the delicate scents of breakfast fare, creating a symphony of tastes that promises to awaken your senses each morning.

Guest Experiences - Imagine unwinding in a cozy lounge area, where despite the bustling street just outside, a serene hush envelops you, allowing whispered conversations and laughter to flourish. A friendly staff member named Mathew ensures your every need is met, effortlessly turning moments into memories while the rich smell of fresh pastries lingers in the air.

Nestled in the historic heart of Windsor, The Castle Hotel offers an exquisite sanctuary where luxury meets royal charm. With the majestic Windsor Castle as your backdrop, each moment unfolds against a canvas of timeless elegance and vibrant local life, making it a perfect romantic getaway or a serene escape for discerning travelers.

Romantic Retreat - Indulge in intimate surroundings that whisper romance at every turn, from the plush furnishings in your luxurious suite to the stunning views of the nearby castle, creating an enchanting atmosphere for couples.

Culinary Delights - Savor the essence of British cuisine at our chic restaurant, Leaf, where the aroma of freshly brewed coffee mingles with the scent of seasonal dishes, offering a delightful brunch experience that lingers long after your meal.

Unmatched Location - Step outside and find yourself in the midst of history, as the sights and sounds of Windsor's vibrant main street dance around you, with the regal 'Changing of the Guards' parade captivating your senses just steps from your door.

Guest Experiences - Guests have relished the delightful surprise of free room upgrades, stepping into beautifully styled junior suites where soft linens and inviting décor create an ambiance of comfort, complemented by a hearty breakfast that sets the tone for a day of exploration.

Nestled between the tranquil banks of the River Thames and the majestic Windsor Castle, the Sir Christopher Wren Hotel offers an enchanting escape steeped in history and wrapped in modern luxury. With the gentle sounds of the river lapping at its edges and the grandeur of the castle standing sentinel nearby, this 17th-century gem invites guests to indulge in romance, relaxation, and the spirited charm of Windsor.

Historic Charm - Step into a world where history whispers through elegant corridors adorned with classic English decor. Each room, uniquely dressed in contemporary style, harmonizes the warmth of tradition with modern comforts, creating a haven that feels both timeless and fresh.

Culinary Delights - Savor the art of dining at The Brasserie, where seasonal ingredients take center stage against a backdrop of stunning river views. Rise each morning to the enticing aroma of a full English breakfast, expertly crafted to awaken your senses and set the tone for a day of exploration.

Outstanding Location - Positioned just moments from the historic Windsor Castle and vibrant local eateries, the hotel serves as a perfect base for cultural explorers and adventure seekers alike. A mere two-minute stroll brings you to the Windsor & Eton Riverside station, effortlessly connecting you to London’s heartbeat.

Guest Experiences - Guests have been charmed by the friendly smiles of staff who greet you like old friends, ensuring every moment is filled with warmth. Imagine enjoying breakfast while gazing out at the shimmering waters of the Thames, the sunlight dancing across your plate—a simple delight that transforms every meal into a cherished memory.

Nestled in the heart of Berkshire's picturesque parkland, Coworth Park - Dorchester Collection exudes an air of refined elegance and tranquility. With its enchanting landscapes and luxurious amenities, this five-star country house invites guests to indulge in a symphony of relaxation and romance, where every detail is designed to awaken the senses and create unforgettable memories.

Total Relaxation - Immerse yourself in the eco-friendly spa, where the soothing fragrances of fresh herbs embrace you as you enter. Enjoy bespoke treatments that harmonize with stunning contemporary architecture, creating an oasis of serenity—a perfect retreat for wellness enthusiasts seeking rejuvenation.

Romantic Escape - Stroll hand-in-hand through 240 acres of manicured grounds, where the gentle sounds of nature provide an idyllic backdrop. The Drawing Room, with its plush furnishings and inviting ambiance, is the perfect setting for intimate afternoon tea, complete with delicate pastries and fragrant brews—all while basking in the soft glow of golden hour.

Adventure Seekers - Experience the thrill of equestrian pursuits at the hotel's exclusive polo fields, or take guided horse-riding lessons tailored to all skill levels. For those who prefer to explore on two wheels, the scenic cycling paths winding through the estate offer breathtaking views of the rolling countryside, inviting exploration at your own pace.

Guest Experiences - Picture the delight of discovering the scrumptious scent of freshly baked treats wafting from the café as you wander the gardens. Guests have relished moments like spotting majestic horses grazing near the hotel while enjoying a morning coffee—an unexpected touch of pastoral charm that enhances the luxury experience.

Nestled in the heart of Slough, Pinfield Boutique Hotel is a romantic retreat that marries chic decor with intimate charm, offering guests an oasis of tranquility just moments from vibrant city life. With its warm ambiance and dedicated service, the hotel invites you to indulge in relaxation while enjoying the comforts of home—an exceptional hideaway where every detail whispers luxury.

Romantic Retreat - Each room at Pinfield exudes a cozy sophistication, featuring exquisite furnishings that invite you to unwind and recharge after a day of exploring. The intimate atmosphere is accentuated by soothing colors and soft textiles, creating a sanctuary perfect for couples seeking a romantic escape.

Total Relaxation - Step into a private world where serene comfort reigns supreme; enjoy spacious en-suite bathrooms equipped with double sinks and luxurious toiletries, making your morning routine a pampering experience. Guests have noted the tranquil ambiance, highlighted by the gentle rustle of leaves outside as you drift into blissful relaxation.

Outstanding Location - Conveniently located near Heathrow Airport yet secluded enough to offer peaceful surroundings, Pinfield serves as a gateway for adventure seekers and cultural explorers alike. Just a short drive away, discover local markets brimming with artisanal delights and scenic walks that reveal the beauty of the English countryside.

Guest Experiences - Upon arrival, the welcoming scent of fresh linens filled the air, and the owner’s thoughtful gesture of pre-warming the room made us feel instantly at ease. As we settled into the cozy lounge with a good book, the quiet hum of the garden outside added a serene soundtrack to our delightful stay.

Nestled within 50 acres of stunning gardens, Great Fosters - Near Windsor is a lavish retreat where Elizabethan grandeur meets contemporary luxury. An oasis of romance and tranquility, it invites couples and solo travelers alike to escape the bustle of everyday life and indulge in its timeless charm.

Romantic Escape - With its beautiful grounds dotted with ancient trees and blooming flowers, every corner of Great Fosters whispers romance. Guests often find themselves enchanted by serene walks through the maze or by the picturesque pond, perfect for quiet moments together.

Culinary Delights - Savor a culinary journey at The Estate Grill, where locally sourced ingredients are transformed into mouthwatering dishes that celebrate simplicity. For those seeking an elevated experience, the sophisticated tasting menus at Tudor Pass provide a delightful exploration of flavors crafted by Head Chef Alex Payne.

Wellbeing Retreat - The hotel’s heated pool beckons for leisurely afternoons under the sun, surrounded by the soothing ambiance of nature. Though deck chairs might show some wear, the overarching relaxation is palpable, allowing guests to unwind while sipping refreshing drinks amid gentle murmurs of laughter and splashes.

Guest Experiences - Upon arrival, the warm welcome from attentive staff set the tone for a memorable stay, turning a birthday into something extraordinary when an unexpected room upgrade brought sheer delight. The scent of fresh pastries wafting from breakfast filled the air, creating an inviting start to the day.

Nestled amid beautifully manicured gardens and serene woodlands, the Macdonald Berystede Hotel & Spa exudes the charm of a French chateau, inviting you to escape into a world of tranquility and indulgence. This luxurious haven is just a stone's throw from the excitement of Ascot Racecourse, making it an ideal retreat for romance, relaxation, and unforgettable moments.

Spa Retreat - Immerse yourself in the soothing ambiance of the Vital Spa, where the gentle ripples of the indoor pool reflect the lush garden views, creating a serene oasis. Savor rejuvenating treatments that awaken your senses, or luxuriate in the outdoor hydrotherapy pool, enveloped by nature’s embrace.

Culinary Delights - Acanthus Restaurant offers a gastronomic journey with its AA Rosette-rated European cuisine, served in an elegant setting that spills onto a sun-kissed terrace. The aroma of freshly prepared dishes mingles with the scent of blooming flowers, making each meal a delightful sensory experience.

Romantic Escape - The intimate atmosphere of the hotel beckons couples seeking a romantic getaway, where elegantly styled rooms provide a cocoon of comfort. Soft white towels and plush robes await after a day spent exploring nearby attractions, enveloping you in pure luxury as you unwind together.

Guest Experiences - One guest delightfully noted how the staff went above and beyond, anticipating their needs with genuine warmth, while another couldn't help but mention the soft touch of the freshly laundered linens that made sinking into the spacious bed feel like a dream come true.

Nestled amidst the lush embrace of National Trust gardens, Cliveden House stands as a timeless testament to elegance and refinement. This historic Italianate mansion, with its palatial architecture, offers an enchanting retreat just a heartbeat away from London, where opulent luxury meets the tranquil whispers of nature.

Romantic Getaway - Indulge in intimate moments under the grandeur of four-poster beds, where every corner invites you to linger a little longer, and the soft rustle of leaves outside serenades your stay with a gentle lullaby.

Spa & Relaxation - Rejuvenate your senses in the luxurious spa, where soothing aromas dance through the air and expert therapists craft bespoke treatments that melt away the day's stresses, leaving you cocooned in serenity.

Outstanding Location - With panoramic views of rolling countryside and a picturesque bend in the River Thames, each sunrise paints your morning with breathtaking colors, inviting you to explore miles of scenic walks and hidden nooks within the estate.

Guest Experiences - One guest marveled at the splendid stillness of the gardens, where they could hear the soft chirping of birds and feel the cool breeze on their skin while sipping tea, enveloped in a world that felt like a secret escape from reality.

Nestled in the heart of Beaconsfield, The Chequers Inn exudes a timeless charm that marries history with modern luxury. As you step into this enchanting 17th-century retreat, the warm glow of an open fire and the inviting scent of freshly prepared meals embrace you, setting the stage for a romantic getaway or a serene escape from the bustle of city life.

Romantic Break - With delicately furnished rooms featuring antique pine furniture and the allure of private terraces overlooking lush gardens, every corner invites couples to unwind and indulge in quiet moments together.

Total Relaxation - Savor leisurely afternoons in the expansive garden, where the gentle rustle of leaves creates a calming symphony, or enjoy an intimate dinner paired with exquisite wines in the award-winning restaurant that champions local flavors.

Historic Charm - The original bar, adorned with oak beams and hardwood floors, radiates character, offering a nostalgic backdrop to sip on carefully selected ales while forging unforgettable memories with friends or loved ones.

Guest Experiences - Amid the tranquility, guests have relished the unexpected delight of a cozy seating area by the fireplace, where the flickering flames cast a warm glow on their conversations, all enhanced by the faint aroma of homemade dishes wafting from the kitchen.

Nestled in the picturesque village of Cookham, Bel and The Dragon-Cookham invites you to experience an enchanting blend of modern luxury and timeless charm. As you approach the hotel, the fragrant blooms of the garden greet you, while the warm glow from the elegantly designed interiors promises an intimate retreat perfect for couples and adventurers alike.

Romantic Break - The atmosphere exudes romance, with thoughtfully decorated rooms that whisper comfort, and a cozy restaurant where candlelight dances across the tables, making every meal feel like a special occasion.

Total Relaxation - Unwind in serene surroundings, whether you choose to indulge in a quiet moment on the garden terrace or explore the nearby scenic walks that invite nature lovers to breathe deeply and reconnect.

Boutique - Each room tells a story, adorned with local artworks and plush textiles that enhance the sense of place; here, every detail is curated to create a chic yet inviting ambiance.

Guest Experiences - Guests have relished the delightful surprise of complimentary whiskey upon arrival, with one visitor noting how this small gesture transformed their evening, as they settled into the inviting nook by the fire, savoring the warmth and sharing laughter with friends.