Boutique hotel vacation rentals in Berkshire County

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Top-rated boutique hotel rentals in Berkshire County

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

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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

5 out of 5 average rating, 4 reviews

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

Perfect for a family or friend getaway with or without your dog in tow, this unit features two luxury pillow-top queen beds, premium linens, a dining table and chairs for work or eating, a sparkling clean bathroom with a shower and a separate sink/vanity area, Roku Smart TV, and individually controlled AC and heat. Quiet, comfy, and comes with full access to East Rock Inn's outdoor dining tables and Adirondack chairs for lounging or enjoying your morning coffee while listening to birdsong.

Top guest favorite

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

5 out of 5 average rating, 9 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 

Superhost

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

Cozy 2-bedroom apartment with AC, fitness room

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

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

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

Superhost

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

4.82 out of 5 average rating, 97 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 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.

A studio room is displayed with a spacious bed and a kitchenette featuring cabinets and essential appliances. A dining area with a wooden table and chairs is present, accented by a vase of flowers. Natural light filters through a window, providing a warm atmosphere.

Hotel room in Becket

Studio Room, with full kitchen

Situated in the charming mountain of Berkshire, MA, The Becket Motel, close to a variety of area attractions, including a scenic hiking, culture activities, (include Jacob's pillow) and shopping. The motel features comfortable accommodations. This room is a studio room with full kitchen inside the room, with all you need and a dinning area. Private bathroom with bathtub include towels and soap.

Superhost

A spacious room is highlighted by a king-sized bed with decorative pillows and a cozy sitting area featuring a queen-size sofa bed. Two small stools are positioned in front of the seating area. Sliding glass doors open to an outdoor space, with a harmonious color palette.

Hotel room in Great Barrington

4.5 out of 5 average rating, 8 reviews

Luxe Unit in Berkshires|King Bed|Sleeps 4|Wifi

Welcome to East Rock Inn, ideally located 1 mile from downtown Great Barrington. Stretch out in our completely renovated Mountain View King Deluxe Room, featuring a king-sized bed, an ample sitting area with a queen-size sofa bed, a bathroom with tub/shower, separate vanity, and amenities from Public Goods. Sliding glass doors lead out to our sprawling backyard and East Rock Mountain.

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

4.75 out of 5 average rating, 4 reviews

Studio|King Bed|Wifi|Dog-Friendly|Prime Berkshires

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 one mile from downtown Great Barrington means you're close to all the shops, restaurants and outdoor activities the Berkshires has to offer.

Superhost

The bedroom features a spacious bed with a plaid blanket and decorative pillows, including one with a bear motif. A wooden bench sits at the foot of the bed. A dining table with two chairs is positioned near a window adorned with white blinds.

Hotel room in Hillsdale

Ultimate Mountain Access Catamount Ski In/Out

Welcome to Catamount! Just steps away from the slopes, our rooms feature exceptional views, unparalleled access, and ideal privacy. You'll also be in the perfect jumping off point for further adventures in Hudson, NY and the rest of the Hudson Valley, or to Great Barrington, MA and the Berkshires beyond. Welcome to the best kept secret in the New York Berkshires!