Boutique hotels in Berkshire County

Find and book unique boutique hotels on Airbnb

Top-rated boutique hotels in Berkshire County

Guests agree: these boutique hotels are highly rated for location, cleanliness and more.

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Superhost
A spacious king bed is prominently featured, adorned with a colorful decorative pillow. A wall-mounted Roku TV is visible, along with a small kitchenette featuring a mini-fridge and coffee supplies. Light filters through the window, while gray curtains frame the room.
Hotel room in Great Barrington
4.8 out of 5 average rating, 5 reviews

Studio|King Bed|Wifi|Dog-Friendly| Near Tanglewood

Designed for a long weekend or intimate stay, with or without your furry family member. This is East Rock Inn's brand new King Studio, featuring a king bed, bathroom with a walk-in shower, and Roku TV. Quiet and comfortable. Our central location, 1 mile from downtown Great Barrington and 1 mile from Butternut Ski Area, means you're close to all the shops, restaurants, and outdoor activities the Berkshires have to offer. A $35/day pet fee applies. Please be sure to indicate if you have a pet.

Superhost
A well-lit room features two spacious queen beds with natural wood headboards, complemented by crisp white linens. A small dining table with black chairs is positioned beside the window, which is framed by light grey curtains. A wall-mounted television is also visible.
Hotel room in Great Barrington
4.86 out of 5 average rating, 7 reviews

Prime Berkshires Studio|WiFi|Sleeps 4|Pet-friendly

Perfect for a family or friend getaway with or without your dog. This unit features two luxury pillow-top queen beds, premium linens, dining table and chairs for work or eating, a sparkling clean bathroom with shower and separate sink/vanity area, Roku Smart TV, and individually controlled AC and heat. With full access to East Rock Inn's outdoor dining tables and Adirondack chairs for lounging or enjoying your morning coffee. A $40/day pet fee applies, capped at $160 for stays of 5+ days.

Guest favourite
The exterior of a three-story resort building is shown, featuring a light-colored facade and multiple balconies. A tranquil pond reflects the structure, surrounded by well-maintained grass and scattered rocks. Lush greenery is visible in the background, enhancing the peaceful setting.
Hotel room in Lee
4.9 out of 5 average rating, 30 reviews

Cozy 2-bedroom apartment with WiFi, fitness room

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

Top guest favourite
A three-story resort building is depicted, featuring a light-colored exterior and a multi-gabled roof. Lush green grass surrounds the structure, and a small pond reflects its image. Nearby trees add a natural element to the scenery, enhancing the relaxing atmosphere.
Hotel room in Lee
5 out of 5 average rating, 7 reviews

Cozy 2-bedroom apartment with AC, fitness room

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

Superhost
A three-story building with a light exterior is surrounded by a grassy area featuring a pond. The calm water reflects the structure and nearby greenery. Pathways and covered decks are visible, suggesting convenient outdoor access.
Hotel room in Lee

Cozy 2-bedroom apartment, AC in welcoming Lee

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

Superhost
The image captures a multi-story building, featuring a light exterior and multiple balconies. A grassy area with scattered rocks surrounds a reflective pond, which mirrors the structure and greenery. Soft morning light enhances the serene landscape.
Hotel room in Lee

Cozy 2-bedroom apartment, AC in welcoming Lee

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

Superhost
A three-story resort building is seen alongside a lush green lawn, featuring multiple balconies and a light-colored exterior. A small pond reflects the structure, surrounded by rocks and grass, creating a serene outdoor setting.
Hotel room in Lee

Cozy 2-bedroom apartment, in enjoyable Lee

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

Superhost
A resort-style building with three levels is surrounded by lush greenery and a tranquil pond. The reflection of the structure can be seen in the water, with rocks lining the edge and a wooden walkway visible in the background.
Hotel room in Lee

Cozy 2-bedroom apartment, WiFi in fabulous Lee

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE.  **Additional charge 

A cozy sleeping area features a spacious bed with a floral-patterned coverlet. There are two bedside tables, each topped with lamps. The room is flanked by windows dressed with plaid curtains, while framed artwork adorns the walls, adding a welcoming touch.
Hotel room in Cummington
4.81 out of 5 average rating, 101 reviews

Singing Bridge Harmony Room

Great views of the Berkshire hilly forests, and hiking trails along a scenic river. Couples, families, and pets feel right at home in our recently renovated kitchen and warm, and friendly lodge with four bedrooms, electric baseboard heat and queen-sized beds. The sunny loft has a comfy queen. Gas heat. Call an hour before arrival if you don't have AT&T or Verizon cell service- other carriers may be inconsistent in the area. Wifi enabled. Pets are welcome for a $25 fee.

A cozy bedroom features a spacious bed draped in a soft down comforter, accompanied by a tray with champagne and fruit. A corner fireplace is surrounded by light curtains and adorned with decorative vases. A blue armchair and a small table enhance the inviting atmosphere.
Hotel room in Lenox
5 out of 5 average rating, 5 reviews

★ Private Peerless Room with Jacuzzi Tub & Fireplace

Known as the Peerless Room, this romantic second-floor space features a Queen bed, corner gas fireplace, and private bath with a Jacuzzi tub. Located in the Carriage House of our historic property, this room offers luxurious amenities and privacy, just a short walk from downtown Lenox. Enjoy daily full breakfast, A/C, HDTV, Wi-Fi, and access to our heated pool (seasonal, Memorial Day - Labor Day). Professionally managed by Hampton Terrace Inn.

The Sunol Room features a cozy layout with a spacious bed adorned with patterned linens. A gas fireplace is set within a white mantel, and a small desk is positioned nearby. Two chairs provide additional seating, with natural light filtering through the window treatments.
Hotel room in Lenox
5 out of 5 average rating, 3 reviews

★ Beautiful Room with Fireplace & Jacuzzi Tub

Known as the Sunol Room, this elegant second-floor space features a Queen bed, corner gas fireplace, and private bath with a Jacuzzi tub. Located in the Carriage House of our historic property, this room offers luxurious amenities and privacy, just a short walk from downtown Lenox. Enjoy daily full breakfast, A/C, HDTV, Wi-Fi, and access to our heated pool (seasonal, Memorial Day - Labor Day). Professionally managed by Hampton Terrace Inn.

A cozy bedroom features a spacious bed with decorative pillows and a warm red throw draped across the foot. Standing lamps provide soft lighting beside the bed. A wooden dresser and a comfortable chair with a green pillow are positioned nearby, creating a restful atmosphere.
Hotel room in Lenox
4.83 out of 5 average rating, 18 reviews

★ Romantic Room with Jacuzzi Tub & Fireplace

Known as the Rarus Room, this moody and romantic second-floor space features a Queen bed, corner gas fireplace, and private bath with a Jacuzzi tub. Located in the Carriage House of our historic property, it offers privacy and is a short walk to downtown Lenox. Enjoy daily full breakfast, A/C, HDTV, Wi-Fi, and access to our heated pool (seasonal, Memorial Day - Labor Day). Professionally managed by Hampton Terrace Inn.

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