Boutique hotels in Berkshire County

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Top-rated boutique hotels in Berkshire County

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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
4.92 out of 5 average rating, 39 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(WAIVED).  **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, 9 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 (WAIVED).  **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(WAIVED) .  **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(WAIVED) .  **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(WAIVED).  **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 corner room features a Queen bed adorned with a sheer net canopy and vintage-style throw pillows. A small table with breakfast items sits beside the bed, while a cozy fireplace is visible. Leaded glass windows allow natural light to brighten the walls of patterned green.
Hotel room in Lenox
5 out of 5 average rating, 4 reviews

★ Vintage Romance with Fireplace & Spa Tub

The Spencer Room is a romantic corner retreat located in the main building, a historic Gilded Age mansion now operating as a boutique inn. It features a Queen bed with a net canopy, vintage throw pillows, antique furniture, leaded glass windows, a corner fireplace, and a private bath with a 72" Ultra spa tub/shower. 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.

Guest favourite
A spacious room features a 4-poster bed with a light quilt, complemented by a cozy seating area with a beige sofa and a small table. A gas fireplace adds warmth, while soft lighting enhances the tranquil blue walls and decorative artwork.
Hotel room in Lenox
5 out of 5 average rating, 6 reviews

★ Romantic King Room w/ Double Jacuzzi & Fireplace

Located in the King Suite Cottages building behind the Main House, the Marion Slocomb Suite is a spacious, private room perfect for a romantic retreat. It features a private entrance, sitting porch, living room area with a gas fireplace, hot tub-size Jacuzzi, wet bar, fridge, 4-poster King bed, A/C, HDTV, and private bathroom. Enjoy daily full breakfast, Wi-Fi, and access to our heated pool (seasonal, Memorial Day - Labor Day). Professionally managed by Hampton Terrace Inn.

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, 104 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.

The spacious Pearl Davis Suite features a four-poster King bed with soft bedding, a comfortable sitting area with a cozy sofa, and an elegant rug with floral patterns. A jetted tub is prominently displayed in the corner, accompanied by fresh flowers in a vase.
Hotel room in Lenox
5 out of 5 average rating, 6 reviews

★Romantic! Fireplace, Jacuzzi & Private Entrance

The spacious and private Pearl Davis Suite in our King Cottage building is perfect for romantic getaways. It features a private entrance, sitting porch, living room with a gas fireplace, 2-person jetted tub, wet bar, fridge, 4-poster King bed, A/C, HDTV, and private bath with a tub/shower combination. Enjoy daily full breakfast, 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 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.

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