The 6 Best Boutique Hotels with Entertainment in The Berkshires (2025)

Nestled in the tranquil embrace of New Marlborough, Gedney Farm emerges as a sanctuary where rustic charm meets modern luxury. Surrounded by lush gardens and rolling hills, this intimate retreat invites couples and adventurers alike to unwind in its serene ambiance, evoking a sense of peace that lingers long after your departure.

Total relaxation - Indulge in rejuvenation at our inviting hot tubs, where the delicate sounds of nature mingle with the soothing warmth of the bubbling water, providing an oasis for contemplation and bliss.

Romantic Break - Experience romance redefined—stroll hand-in-hand through picturesque walking trails or savor intimate candlelit dinners at our on-site restaurant, where each dish is a celebration of local flavors crafted with care.

Country Escape - Embrace the simplicity of rural life, with opportunities to explore local markets brimming with artisanal goods and hiking trails that reveal breathtaking vistas, perfect for creating unforgettable memories with loved ones.

Guest Experiences - The gentle rustle of leaves and distant chirps create a peaceful soundtrack as you sip morning coffee on the terrace, while the charming imperfections of vintage furnishings add character to each room, making it feel like a cherished escape from the everyday.

Step into a world where history meets luxury at The Red Lion Inn, nestled in the quaint charm of Stockbridge, Massachusetts. Here, each room whispers tales of yesteryear, adorned with antiques that evoke nostalgia, while modern comforts promise an unforgettable experience for romantic getaways or serene solo retreats.

Historic Charm - Wander through hallways that are alive with character, where every nook offers a glimpse into the past, from delicate birdcage elevators to delightful tea pots gracing the rooms. Guests often find themselves lost in the enchanting details reminiscent of a bygone era.

Culinary Delights - Savor exquisite American cuisine in the hotel’s elegant dining spaces, where the clinking of silverware harmonizes with the soft murmur of conversation and occasional laughter, creating the perfect backdrop for a memorable meal. Each dish is crafted not just to satisfy hunger but to ignite the senses.

Intimate Relaxation - Unwind by the year-round outdoor pool or luxuriate in the hot tub, enveloped by the gentle sounds of nature and the fresh scent of blooming gardens. Whether you're soaking in the warmth or sharing stories with friends on the sun-soaked patio, tranquility is just a heartbeat away.

Guest Experiences - Guests delight in the unexpected, like discovering the cozy basement bar filled with jazz melodies and attentive bartenders, while sipping cocktails under the dim lights. The sight of 'Jane,' the friendly inn cat, weaving through the guests adds an extra touch of homely charm, making conversations feel like old friends reuniting.

Nestled in the heart of Hudson, Wm. Farmer and Sons envelops you in a chic and romantic ambiance, where modern elegance meets rustic charm. From the moment you step inside, the subtle scent of freshly brewed coffee mingles with the cozy warmth of gas fireplaces, inviting you to unwind and indulge in a peaceful retreat away from the bustling world outside.

Romantic Break - Experience an enchanting escape with beautifully designed rooms that boast sumptuous bedding and soft lighting, perfect for intimate evenings and cozy cuddles.

Cultural Explorers - Immerse yourself in local culture as you wander through charming streets lined with unique boutiques, art galleries, and historic sites, all just a stone's throw away from your luxurious hideaway.

Spa & Relaxation Lovers - Indulge in well-deserved relaxation as you soak in the deep bathtubs, wrap yourself in plush robes, and surrender to the soothing atmosphere of this boutique sanctuary.

Guest Experiences - After a long day of exploring, guests have cherished the delightful service from staff like Minnie, whose thoughtful gestures—like recommending dog-friendly dining options—transform a simple stay into a memorable adventure filled with genuine care.

Nestled in the heart of Albany, The Argus Hotel & Cocktail Lounge invites guests to experience a harmonious blend of historic charm and modern luxury. With its warm ambiance and stylishly appointed interiors, this boutique hotel serves as an intimate retreat, perfect for couples seeking romance or solo travelers yearning for personal rejuvenation.

Romantic Break - Indulge in quiet moments amidst elegant surroundings, where each room encapsulates a sense of serenity, allowing lovebirds to unwind and connect while gazing out at the charming city views.

Cultural Explorers - Immerse yourself in Albany's rich history, with cultural landmarks just a stone’s throw away; from the ornate New York State Capitol to the dynamic performances at The Egg Center, adventure awaits around every corner.

Total Relaxation - Revel in the tranquil garden setting or sip crafted cocktails in the lounge, where the soft murmur of conversation blends seamlessly with the clinking of glasses, creating an inviting atmosphere to relax after a day of exploration.

Guest Experiences - As you step into the lobby, the friendly warmth of Jess, the receptionist, instantly envelops you. Her enthusiasm is contagious, making you feel less like a guest and more like an old friend returning home. And as you sink into the plush bed, the comforting scent of fresh linens fills the air, promising a restful night ahead.

Nestled amidst the lush landscape of Washington, Connecticut, The Mayflower Inn & Spa beckons with its luxurious charm and serene elegance. As you step into this exquisite retreat, you're enveloped in a world where timeless sophistication meets intimate hospitality, setting the perfect tone for romance, rejuvenation, or simply an escape from the everyday.

Total Relaxation - Indulge in unparalleled calm at the award-winning spa, where the soothing sounds of nature blend seamlessly with the gentle melodies of soft music. Here, expert therapists will guide you on a journey to wellness, enveloping you in aromatic scents that linger long after your treatment ends.

Romantic Break - Experience moments that spark joy as you stroll through the immaculately landscaped gardens, where vibrant blooms and whispering trees create an idyllic backdrop for love. Pair your leisurely walk with a cozy evening by the fire, sharing s'mores under a star-studded sky—an enchanting experience that feels both intimate and unforgettable.

Spa Breaks - The Mayflower Inn's spa is a sanctuary of serenity, inviting guests to unwind in plush robes while sipping herbal tea infused with local herbs. Each treatment promises not just relaxation but a sensory feast, from the warm oils that glide over your skin to the tranquility that wraps you like a soft blanket.

Guest Experiences - Guests have shared heartwarming tales of connection—like when Chris greeted them with genuine warmth upon arrival, ensuring their every need was catered to, or how Katy’s late-night conversations and thoughtful gestures, like serving s'mores by the crackling fire, added a personal touch that transformed their stay into an experience filled with cherished memories.

Nestled amidst the breathtaking peaks of the Green Mountains, The Equinox Golf Resort & Spa is a sanctuary of sophistication and serenity. With its rich history echoing through elegant halls and lush grounds, this retreat invites you to indulge in luxury while savoring the enchanting allure of Vermont's natural beauty.

Spa Retreat - Step into a haven of tranquility at the full-service spa, where the soothing scents of essential oils mingle with the sound of gentle water features, creating an ambiance perfect for rejuvenation. Each treatment is designed to whisk you away from the everyday, enveloping you in pure bliss.

Culinary Delights - Experience culinary artistry at The Chop House, where sumptuous cuts of steak are expertly paired with fine wines, or unwind outdoors at the Dormy Grill, savoring fresh seasonal dishes kissed by the mountain breeze. Every meal feels like a celebration against the stunning backdrop of the landscape.

Adventure Awaits - From the thrill of off-road driving through picturesque trails to horseback riding that immerses you in nature’s splendor, every experience beckons adventure seekers to embrace the great outdoors. Explore the charming trails or cozy up by a crackling fire after a day filled with excitement.

Guest Experiences - A couple relished their morning coffee on the terrace, the aroma mingling with crisp mountain air, as they shared laughter over stories told by the attentive staff who made them feel cherished and special. Meanwhile, the vibrant autumn leaves painted a breathtaking panorama, creating picture-perfect moments at every turn.