Best Short-Term Rentals in Great Barrington

Wainwright Inn offers accommodations in Great Barrington, 14 miles from Tanglewood Musical Center and 14 miles from Tanglewood. 9.3 miles from Norman Rockwell Museum and 13 miles from Cranwell Spa & Golf Club, the property offers a garden and a terrace. The bed and breakfast also features free Wifi, free private parking, and facilities for disabled guests. Some accommodations include a balcony and a seating area with flat-screen TV, as well as air conditioning and heating. At the bed and breakfast, some units are allergy-free. À la carte and American breakfast options with fresh pastries, pancakes, and fruit are available each morning at the bed and breakfast. Skiing, cycling, and hiking are possible within the area, and Wainwright Inn offers ski storage space. Great Falls is 12 miles from the accommodation, while Canaan Village Historic District is 12 miles from the property. The nearest airport is Bradley International Airport, 51 miles from Wainwright Inn.

- "Exceeded our expectations. Breakfast was delicious and bed very comfortable" - "Our stay was comfortable and pleasant." - "Thanks to Chris and Barb, I'm looking forward to staying there again!" - "Very enjoyable time with everything we needed and more. Would definitely stay there again."

Bed & breakfast with free parking, in the vicinity of Ski Butternut
This smoke-free bed & breakfast features coffee/tea in a common area, concierge services, and express check-in. Free WiFi in public areas and free self parking are also provided. Other amenities include express check-out.
The Barrington offers 7 accommodations with complimentary bottled water and coffee/tea makers. These individually decorated accommodations have separate sitting areas and include desks. Beds feature premium bedding. Flat-screen televisions come with premium cable channels.

Bathrooms include bathrobes, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and portable fans. Housekeeping is provided daily.

- "Great stay, the room was as advertised, delicious breakfast included and great location. Will stay again. " - "As always, our stay at The Barrington was wonderful. The rooms are large, lovely and the bed comfortable. The service is great and everyone is so friendly and accommodating! The breakfast is delicious. We truly enjoy our stay, every time!" - "We absolutely loved our stay at The Barrington. The staff is lovely. The room was huge, beautiful and quiet. The breakfast was incredible. We will definitely be back. "

Located in New Marlborough, 17 miles from Norman Rockwell Museum, The Old Inn On The Green provides accommodations with a seasonal outdoor swimming pool, free private parking, a garden and a restaurant. With a bar, the 4-star inn has air-conditioned rooms with free WiFi, each with a private bathroom. Tanglewood is 21 miles away and Haystack Mountain State Park is 11 miles from the inn. At the inn, each room includes a closet. At The Old Inn On The Green each room has bed linen and towels. Guests at the accommodation will be able to enjoy activities in and around New Marlborough, like hiking. Cranwell Spa & Golf Club is 20 miles from The Old Inn On The Green, while Tanglewood Musical Center is 20 miles away. The nearest airport is Bradley International Airport, 37 miles from the inn.

- "Nice trip in the Berkshires." - "Charming stay."

Inn with free breakfast, near Questing
A restaurant, a bar/lounge, and a coffee shop/cafe are available at this inn. Free continental breakfast is provided, as well as free WiFi in public areas, free self parking, and a free manager's reception. Additionally, a seasonal outdoor pool, a meeting room, and a garden are onsite.
The Old Inn On The Green offers 11 air-conditioned accommodations with hair dryers and complimentary toiletries. Rooms open to balconies or patios. Each accommodation is individually furnished and decorated. Beds feature premium bedding. Televisions come with cable channels. Guests can surf the web using the complimentary wireless Internet access. Housekeeping is provided daily.
Recreational amenities at the inn include a seasonal outdoor pool.

- "It was great experience. " - "Everything was wonderful - the food was delicious and the staff very attentive at dinner. The only thing that was a bit off-putting was that there were two leftover red wine glasses left out on the table on the balcony that we wished had been removed before our arrival, but that's just a little thing. " - "What a wonderful experience, including the exceptional restaurant!" - "Built in 1750, The Old Inn On The Green is a rare and remarkable testament to colonial America, Under the deft leadership of owner Peter Platt with the meticulous guidance of his superlative dining manager, Eric, the Inn offers an authentic bygone-era dining and lodging experience unlike any other. From the moment you step inside, you are transported back to the 18th century. The inn’s structure, largely untouched by time, is steeped in history, with its original wooden beams and creaking floorboards preserving the aura of its storied past. But perhaps what sets the atmosphere apart is the dining room— menu changes with the seasons, reflecting the bounty of the surrounding area. Exquisite dishes of finely roasted, richly-flavored choice meats in velvety sauces takes you back to the days when hunters supplied the village of New Marlborough with game. Fresh fish and seafood delicacies from New England’s fabled coastal fishing fleet are transformed into succulent briny ocean masterpieces that would rival any Michelin-starred restaurant in New York or Paris. The inn offers authentic 18th-century coach house accommodations that further immerse guests in the past. Each room is meticulously furnished with period-appropriate decor, from wood hewed beds draped in fine linens to hand-crafted wooden chests and writing desks. The Old Inn is not just a place to eat and sleep—it is an experience, a living museum of New England’s colonial past. HIGHLY RECOMMENDED!! "

Berkshire Vacation Rentals: Great Barrington Walkable To Lake And Town is located in Great Barrington, just 14 miles from Cranwell Spa & Golf Club and 14 miles from Tanglewood Musical Center. The air-conditioned accommodation is 10 miles from Norman Rockwell Museum. Canaan Village Historic District is 13 miles away and Holley Williams House Museum is 19 miles from the vacation home. With free Wifi, this 3-bedroom vacation home features a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the vacation home. The accommodation has a fireplace. Guests can relax in the garden at the property. Tanglewood is 14 miles from the vacation home, while Great Falls is 13 miles from the property. Bradley International Airport is 48 miles away.

Fireplace/Heating • Internet • Parking • Air Conditioner • View • Security/Safety • Pet Friendly

Colonial inn with a nightclub and a coffee shop
Along with a restaurant, this smoke-free inn has a nightclub and a bar/lounge. Free WiFi in public areas and free self parking are also provided. Other amenities include a coffee shop/cafe, a meeting room, and dry cleaning.
The Egremont Village Inn offers 10 accommodations with complimentary toiletries. Beds feature premium bedding. This South Egremont inn provides complimentary wireless Internet access, with a speed of 250+ Mbps (good for 3–5 people or up to 10 devices). Irons/ironing boards and hair dryers can be requested. Housekeeping is provided daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

- "The restaurant/bar on the premises was EXCELLENT, and allowed us to visit the country and have the freedom to have a drink and shoot some pool. A great place, with incredibly friendly owners." - "Our stay was wonderful. We came into town for my grandmothers funeral, we were a little confused as check in is contactless, but we met Rosa and communicated via text and it was easy sailing after that. They did inform me of contactless check in, it just slipped my mind with all going on. The property was great, loved spending one morning with the cows and later with the two pups on site. Really loved that the animals were rescues. Our room was small, but cozy, plenty of other rooms to relax in or play cards. But the heart of this Inn lies with Rhonda, who took very good care of us during our stay. She was so empathetic and warm and welcoming and helped ease the burden of what could have been a very stressful trip back. It was a healing expierence, and ill never forget that, and I thank her and everyone else there. I hope to visit and stay again sometime."

Berkshire Vacation Rentals: Peaceful Post and Beam Loft Sleeps 9 offers accommodations in New Marlborough, 15 miles from Norman Rockwell Museum and 17 miles from Cranwell Spa & Golf Club. This vacation home features air-conditioned accommodations with a patio. Great Falls is 14 miles from the vacation home and Canaan Village Historic District is 14 miles away. With free Wifi, this 1-bedroom vacation home provides a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and microwave. Towels and bed linen are provided in the vacation home. For added privacy, the accommodation features a private entrance. Guests can also relax in the garden. Tanglewood Musical Center is 17 miles from the vacation home, while Tanglewood is 18 miles away. Bradley International Airport is 40 miles from the property.

Pet Friendly • Air Conditioner • Internet • Security/Safety • View • Parking • Fireplace/Heating

Hotel in Great Barrington with free breakfast and a restaurant
A restaurant, a bar/lounge, and a refrigerator in a common area are available at this hotel. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include conference space, wedding services, and a garden.
Gedney Farm offers 16 air-conditioned accommodations with hair dryers and complimentary toiletries. Each accommodation is individually furnished. This Great Barrington hotel provides complimentary wireless Internet access. Microwaves, refrigerators, and irons/ironing boards can be requested. Housekeeping is provided daily.
The recreational activities listed below are available either on site or nearby; fees may apply.

- "The grounds were beautiful and staff were so nice! Dinner was delicious!" - "It's been the fourth time I stayed at the Gedney Farm. IT's gorgeous, beautiful setting, friendly hosts, amazing room with whirlpool in the old barn. I will come back!" - "Quiet surrounding is great to rekax" - "Absolutely a wonderful experience. It was just what i was looking for. Truly unique, very comfortable, surrounded by beauty and nature. Gracious host. Win, win. We will be back."

Berkshire Vacation Rentals: High End Berkshires Getaway offers accommodations in East Hillsdale, 16 miles from Norman Rockwell Museum and 20 miles from Cranwell Spa & Golf Club. This vacation home features air-conditioned accommodations with a patio. Tanglewood Musical Center is 21 miles away and Tanglewood is 21 miles from the vacation home. With free Wifi, this 4-bedroom vacation home offers a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are featured in the vacation home. The accommodation has a fireplace. Great Falls is 15 miles from the vacation home, while Canaan Village Historic District is 15 miles away. Bradley International Airport is 54 miles from the property.

Air Conditioner • Security/Safety • Pet Friendly • Parking • Fireplace/Heating • Internet

Comfortable inn with free breakfast and business center
This smoke-free inn features an outdoor pool, a restaurant, and a bar/lounge. Free buffet breakfast, free WiFi in public areas, and free self parking are also provided. Other amenities include a snack bar/deli, a business center, and a meeting room.
Housekeeping is available once per stay.
Thornewood Inn offers 13 air-conditioned accommodations with complimentary toiletries. Beds feature premium bedding. Cable television is provided. Bathrooms include bathtubs or showers.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include desks and phones; free local calls are provided (restrictions may apply). Housekeeping is offered daily and hair dryers can be requested. Housekeeping is provided once per stay.

- "We loved the quaintness and character of Thornwood Inn plus the history of it being run by the same family for almost 40 years! Terry and David were wonderful hosts, chatting with us and always ready to answer any questions we had. Homemade breakfast each morning was delicious and presented in a very appetizing way with fresh fruit every day and Terry’s baked “goodies” were a treat!! Short drive to Great Barrington and Stockbridge for shopping and eating out with a variety of restaurants available. Also a number of hiking trails were just a quick drive away. We thoroughly enjoyed our stay at the Thornwood Inn and hope to return again. Claudia J."

Berkshire Vacation Rentals 1900s Factory Turned Modern Berkshires Retreat is located in Great Barrington, just 6.2 miles from Norman Rockwell Museum and 11 miles from Tanglewood Musical Center. Both free Wifi and parking on-site are accessible at the vacation home free of charge. Great Falls is 15 miles from the vacation home and Canaan Village Historic District is 15 miles away. Berkshire Vacation Rentals 1900s Factory Turned Modern Berkshires Retreat features 4 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. A TV is available. The accommodation has a fireplace. Guests can relax in the garden at the property. Tanglewood is 11 miles from the accommodation, while Cranwell Spa & Golf Club is 12 miles from the property. Bradley International Airport is 48 miles away.

Child Friendly • Parking • Air Conditioner • View • Internet • Fireplace/Heating • Security/Safety

Hotel in North Egremont with a sauna and spa services
This smoke-free hotel features an outdoor pool, a restaurant, and a bar/lounge. Free WiFi in public areas and free self parking are also provided. Other amenities include a sauna, a coffee shop/cafe, and spa services.
Housekeeping is available once per stay.
Prospect Berkshires offers 49 accommodations with minibars and hair dryers. Beds feature Egyptian cotton sheets, down comforters, and premium bedding. Guests can surf the web using the complimentary wireless Internet access (speed: 500+ Mbps (good for 6+ people or 10+ devices)). Housekeeping is offered once per stay and in-room massages can be requested. Housekeeping is provided on a limited basis.
Recreational amenities at the hotel include an outdoor pool, a sauna, and complimentary bicycles.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "So fantastic!! The cabins are gorgeous and very well appointed. We are going back!" - "It was clean and environment is relaxing." - "Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway "

Berkshire Vacation Rentals: Private Estate Heated YEARROUND Outdoor Pool offers accommodations in North Egremont, 12 miles from Norman Rockwell Museum and 16 miles from Tanglewood Musical Center. Both free Wifi and parking on-site are available at the vacation home free of charge. The vacation home also offers an outdoor swimming pool and a garden for guests to relax in. Berkshire Vacation Rentals: Private Estate Heated YEARROUND Outdoor Pool features 7 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 5 bathrooms with a hair dryer. Towels and bed linen are provided in the vacation home. For added privacy, the accommodation features a private entrance. Tanglewood is 17 miles from the accommodation, while Cranwell Spa & Golf Club is 19 miles away. Albany International Airport is 50 miles from the property.

Pool • View • Fireplace/Heating • Ev Charge Station • Security/Safety • Air Conditioner • Parking • Pet Friendly • Internet

While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and free WiFi, as well as air conditioning and laundry facilities. Other amenities include premium bedding, a memory foam bed, towels, and luggage storage.

Parking • Other • Bedding/Linens • Internet • Laundry • Fireplace/Heating • Guest Services • Pool • Security/Safety • Toiletries • Air Conditioner • Wellness Facilities

Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To Town offers accommodations in Great Barrington, 8.9 miles from Norman Rockwell Museum and 13 miles from Cranwell Spa & Golf Club. This vacation home provides air-conditioned accommodations with a patio. Great Falls is 13 miles away and Canaan Village Historic District is 13 miles from the vacation home. With free Wifi, this 3-bedroom vacation home features a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Guests can relax in the garden at the property. Tanglewood Musical Center is 13 miles from the vacation home, while Tanglewood is 13 miles from the property. Bradley International Airport is 47 miles away.

Security/Safety • View • Fireplace/Heating • Parking • Air Conditioner • Pet Friendly • Internet

Hotel in Great Barrington with free breakfast and a fitness center
This smoke-free hotel features a fitness center, coffee/tea in a common area, and a microwave in a common area. Free on-the-go breakfast is provided, as well as free WiFi in public areas, free self parking, and a free manager's reception. Other amenities include a 24-hour front desk, free newspapers, and barbecue grills.
Change of towels is available on request.
Quality Inn offers 63 air-conditioned accommodations, which are accessible via exterior corridors and feature coffee/tea makers and complimentary weekday newspapers. Rooms open to balconies or patios. Pillowtop beds feature premium bedding. Premium cable television is provided. Rooms have partially open bathrooms. Bathrooms include shower/tub combinations with deep soaking bathtubs and hydromassage showerheads, complimentary toiletries, and hair dryers.

This Great Barrington hotel provides complimentary wireless Internet access. Business-friendly amenities include desks along with free local calls (restrictions may apply). Additionally, rooms include irons/ironing boards and fans. Microwaves and change of towels can be requested. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Property was clean and comfortable." - "Everything was great! We'll be back." - "Good value. Nice staff" - "Great breakfast! Good size rooms! Comfortable beds! Slept better than in my own bed. Location is also quite a plus, ten steps from town, and quite a lovely town!! " - "It’s in “downtown” Great Barrington very close to the Mahawie theatre. Very clean rooms. Only criticism I have is that the Wi-Fi was not working. Good continental breakfast. Friendly and helpful staff. "

Located in Great Barrington, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires has air-conditioned rooms with free WiFi. Featuring family rooms, this property also provides guests with a playground. Tanglewood Musical Center is 12 miles away and Tanglewood is 12 miles from the hotel. The hotel offers a buffet or continental breakfast. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires offers 3-star accommodations with an indoor pool, fitness center and hot tub. Guests at the accommodation will be able to enjoy activities in and around Great Barrington, like hiking and skiing. Free private parking and a business center are available, as well as a 24-hour front desk. Norman Rockwell Museum is 7.6 miles from Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, while Cranwell Spa & Golf Club is 11 miles from the property. Bradley International Airport is 47 miles away.

- "Recent visit." - "Exceptionally clean & very friendly staff. Will definitely go back!" - "Excellent stay. Super nice staff" - "Perfect for a skiing weekend with family" - "Enjoyable, convenient location." - "AWESOME" - "The staff was friendly, the hotel was quiet allowing everyone to sleep when they wanted to." - "Very good stay with nice friendly staff." - "Very comfortable room and excellent location." - "Great hotel near outlets for a quick getaway"

Motel in Great Barrington with free parking
Along with barbecue grills, this smoke-free motel has a picnic area and free self parking. WiFi in public areas is free.
Monument Mountain Motel offers 17 air-conditioned accommodations with coffee/tea makers and hair dryers. Cable television is provided. Refrigerators and microwaves are provided. Bathrooms include shower/tub combinations and complimentary toiletries.

This Great Barrington motel provides complimentary wired and wireless Internet access. Business-friendly amenities include phones along with free local calls (restrictions may apply). Housekeeping is provided daily.

- "Very convenient and affordable price!!" - "No frills, but very clean. Furniture is old, but bedding is new. Shower area recently redone. Two feet between dresser and bed, which is plenty. Side table on each side of bed. Excellent value." - "It was convenient to everything and everyone was delightful. " - "Clean and comfortable. Perfect for an over night in the Berkshires. Very reasonable priced for the area. " - "Place was small, but clean & comfortable. Loved that it had microwave & mini fridge"

Great Barrington’s Thornewood Inn is a bed and breakfast that features antique furniture throughout the property. The inn has an outdoor pool and a deck facing the Berkshire Hills. The Point is Thornewood Inn’s on-site restaurant and serves continental cuisine. They offer a complimentary breakfast in the morning and have scheduled live entertainment. Rooms are decorated with antique furniture and individual themes. Each room has an en suite bathroom and access to free Wi-Fi. The Norman Rockwell Museum is located 7 miles from the property, and Ski Butternut is 6 minutes drive from the inn.

Pool • Internet • Balcony/Terrace • Air Conditioner • Wheelchair Accessible • Child Friendly • Parking • Pet Friendly • Breakfast

Hotel with free breakfast, near Housatonic River Walk
An indoor pool, a 24-hour fitness center, and coffee/tea in a common area are available at this smoke-free hotel. Free continental breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, a business center, a meeting room, and dry cleaning are onsite.
Housekeeping is available on request.
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires offers 93 accommodations with safes and complimentary newspapers. 49-inch flat-screen televisions come with premium cable channels. Refrigerators, microwaves, and coffee/tea makers are provided. Bathrooms include complimentary toiletries and hair dryers.

This Great Barrington hotel provides complimentary wired and wireless Internet access. Business-friendly amenities include desks and desk chairs, as well as phones; free local calls are provided (restrictions may apply). Additionally, rooms include irons/ironing boards and blackout drapes/curtains. Change of towels and change of bedsheets can be requested. Housekeeping is provided daily.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "The staff was extremely, I can not stress this enough, extremely nice and helpful." - "Very friendly and helpful staff. " - "My family and I went to a religious event. The hotel staff was aware of the event; they were very welcoming. Customer service was amazing; continental breakfast was great! " - "Excellent service during breakfast, friendly staff and clean facility. " - "Great property. The pool and hot tub were nice, but over chlorinated. "