Best Lodging Options 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. "

Downtown Great Barrington Enjoy Mountain Views offers accommodations in Great Barrington, 9.3 miles from Norman Rockwell Museum and 14 miles from Cranwell Spa & Golf Club. This vacation home offers air-conditioned accommodations with a patio. Tanglewood Musical Center is 14 miles away and Tanglewood is 14 miles from the vacation home. With free Wifi, this 3-bedroom vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Guests can relax in the garden at the property. Great Falls is 13 miles from the vacation home, while Canaan Village Historic District is 13 miles from the property. Bradley International Airport is 47 miles away.

- "Wonderful" - "Please see above" - "EXCELLENT!!!!! Beautiful, comfortable home and gardens!" - "Great location for a girls weekend."

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.

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

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.

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

Bedding/Linens • Balcony/Terrace • Kitchen • Child Friendly

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.

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

In 2016 Smithsonian Magazine deemed Great Barrington, "The Best Small Town in America." Manor Lane is a private French Country Estate located only 5 minutes from the heart of the Berkshires. Situated 10 minutes to both Butternut and Catamount ski mountains and 25 minutes to Tanglewood.
Manor Lane is a private Estate where each room has been endowed with notable charm. A French Manor House with private pool and tennis court, formal living and dining rooms, fireplace, study and unique Gauguin Bar. The house has welcomed numerous noteworthy guests along the way including: Donovan, Roger McGuinn and Leslie Gore, jazz artists; Bobby Watson, John Hicks and Victor Lewis.
Settle into the relaxing tempo of Manor Lane and let us indulge you with the kind of thoughtful extras that we take pleasure in providing.

- "Lovely house" - "A romantic Chateau in the Berkshires" - "This is one of the most beautiful homes we have stayed in, in years of VRBO stays around the world. Excellent in every way, down to the last detail. Ash, NYC" - "We were taking our first family ski trip and were lucky to stay at this great house which is only 10 minutes from Butternut. Super convenient, very comfortable and the huge kitchen was a perfect place for our family to gather after a day on the slopes. We loved it and would happily return next year!"

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

Located in the beautiful Berkshires, MA, the 5000 sqf home is located in a desired neighborhood known as "the Hill.” The sun filled house is on a quiet no outlet road and sits on 2.5 acres of landscaping including blueberry bushes, maple tree, lawns, mature flowers, and custom cobblestone. In spite of being only a 15 min walk from downtown, it feels very away from it all with trees in every window and privacy.

Connections to the Appalachian trail within 10 minutes. Lake Mansfield is a 15 min walk. The Green River, with a swimming hole, is a 15 min hike through the woods. The Mahaiwe, a movie theater and the great thriving restaurants, boutiques, toy stores and coffee shops of downtown are a 15 minute walk. Tanglewood is a 20 minute drive. Butternut is a 10 minute drive.

The historic home was built in 1905 and was one of the first in Great Barrington to receive electricity. It has been lovingly renovated and restored from the ground up. Many original details were restored to new condition (windows, radiators and the like) and modern conveniences added. There is central air conditioning, whole home audio system, movie room w/ mounted 65 inch 4k television, surround sound, double pane windows, heated floors in the bathrooms and kitchen. There is a second 4k television in the den for when the kids don't want to watch the same movie as the adults - also with high end surround sound. Sony Playstation and multiple streaming devices all updated to 4K technology. The gourmet cook's kitchen includes a large granite prep area, 2 deep sinks, Wolf Stove, large SubZero, and 2 Bosch dishwashers for easy clean up.

The house is oversized but still cozy with brand new sheets from Brooklinen, new towels, lots of blankets, and well designed locally bought furniture and rugs. There are games and a library of classics and NYTimes bestsellers for ages 2 - adult. In keeping with the classic feel, there is a high end record player in the library for afternoons playing chess and cards. Two large wood burning fireplaces make it homey during the winter.

Enjoy the fresh summer air on the large screened in porch, play ping pong, or enjoy a meal in the fresh air on the screened porch dining table. Ample lawns and private outdoor space, especially for an in town property. Weber Grill on large stone patio for for preparing summer meals, nine person sunken hot tub on mahogany deck and a wood swing set and slide set up for the kids.

Nursery was painted and set-up in 2022 and has toddler toys available for use. Farrow and Ball paint and natural fiber rugs used throughout most of the house. Fragrant free and organic or non-toxic cleaners used. Plates and serving ware for 12 from Crate and Barrel, new in Fall 2024.

Also available for seasonal or year-long rental.

- "On a quiet street and walking distance to town, this renovated Victorian was a great place for the family to relax. Many alcoves for privacy or work were a real plus. Only issue is slow Wi-Fi, but a great overall stay." - "We loved the home. It was very conducive to relaxing and spending time with family. There are many spots to hang out in, nap, or read. We enjoyed walking to town for coffee at Fuel each morning. We also did some fantastic hikes. We also loved the fancy appliances and gadgets in the kitchen. And the ping pong table was a nice distraction during the warmest part of the day. The host was very responsive and we will definitely return."

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.

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

Well appointed Vacation Cottage, newly renovated by the Owners; An Architect and an Interior Designer as a Modern Farmhouse.
5 bedrooms, 4 bathrooms, 2 large living rooms, an entertaining playroom and a well-equipped Kitchen, Front and Rear covered porches w/ a Hot Tub overlooking the open forest view.
The large open lawn hosts volleyball net, soccer goals, picnic tables with lighting for outdoor dining, Solo fire pit sitting area, BBQ grill and yoga matts for your early am flow.
The Hot Tub for 5 is conveniently located under the covered rear porch overlooking the forest. 5 min drive from Lake Mansfield and the town of Great Barrington and other beautiful surrounding hiking trails.
Complete privacy yet only about 10 min drive from 2 Ski resorts, Butternut & Catamount. 5 min drive from Lake Mansfield and the town of Great Barrington and other beautiful surrounding towns with many options for Restaurants, Shopping, Balling Ally’s, Music & Theatre events and festivals & hiking trails, one would never get bored.

Climbing only 3 steps to the front deck, entering the house into a double ht. foyer that leads to an open floor plan

The house is fully air-conditioned/heated with ample storage and closets for shoes, ski gear and coats. Walking into an open floor plan; Kitchen, Dining & couched Fireplace sitting area & Living Rooms.

The kitchen is fully equipped and has an eat-in island (sits 5). The dining table is large enough to for great family and friends gatherings.

The house has 2 separate large Living Rooms, each equipped with 75” HD smart TV and large sectional sofas.

The playroom includes a full size double Pop-A-Shot (double hoop basketball game), Air Hockey table, a Foosball table, XL Janga, Remi cube, Bingo and other board games.

The Laundry room equipped with 2 Washer machines and 2 Dryers.

The 2nd floor includes a Yoga space / Sitting area overlooking the forest, 2nd Master bedroom, oversized King room with office space and anther bathroom with tub.

Bedrooms:
#1 - Master Bedroom #1 - On First Floor - Queen size bed with private oversize bathroom & jungle shower with 2 windows overlooking the woods while you shower.
The Bedroom includes a comfortable armchair & side table, light night, closet and dresser.

#2 - Master Bedroom #2 - On 2nd Floor - Queen size bed with private bathroom & jungle shower.
The Bedroom includes a comfortable armchair & side table, 2 light night, closet and dresser.

#3 - King Bedroom - On 2nd Floor - Extra Large bedroom with a King size bed and a pull out twin bed and a twin open sofa The room has an eclectic collection of furniture to provide comfort and function with a reading nook. The Bedroom includes a comfortable armchair & side table, light night, closet and dresser.
The full bathroom with a tub is across from it.

#4 - Queen Bedroom - Queen size bed with a built-in loft over it with a twin mattress. The Bedroom includes a side table, light night, closet and
Dresser.

#5 - Bunk Bedroom - Sleeps 4 on twin size mattresses on 2 bunk beds. The Bedroom light night for each bed personal cabbie unit for each of the 4 guest.

The 4th full bathroom is located on the first floor.

Each Queen bed has 4 pillows (2 down pillows and 2 alternatives and a down comforter).

- An Office / Open Gallery Space is located on the upper floor with a sofa and a trundle bed under it, providing additional two twin size sleeping beds arrangement.
Each guest gets 2 large towels.
Important highlight features - Covid prevention Committed, Completely fenced backyard, private parking spaces, Strong WiFi, the house is Fully Air-Conditioned.

Night light for each bed and Designated storage space for each of the guests
European comfort - all bed linens are are 100% Cotton/400-600 thread.
Down pillows & white goose Down comforters.

The Cottage has an Alarm system and security cameras that are directly connected 24/7 Fire & Police departments. Outdoor Solar lights around the back yards. And a smokeless fire pit (Solo) & Hot Tub for 5.

- "House is beautiful and very comfortable. Each bedroom and bath was welcoming and cheerful. The kitchen is well stocked with cookware, dishes, and spices!! Big fenced well-tended yard with lots of seating choices. BBQ grill made cooking easy. Air-conditioners worked well and Wi-Fi strong to make it a very nice comfortable and productive stay (if you have to do some work). Great house that is 10min drive to Great Barrington Town Center making foods pharmacy, and other shopping very easy. Shay was always responsive making any issues easy to solve. Thanks Shay for a great stay."

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.

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

Built in 2015, this lovely 4 bedroom, 2500 sq.ft. home on a knoll is set back 175 feet from the street. This charming home offers privacy and flexibility for multi generational groups. There are 2 queen bedrooms, and 2 bedrooms with two twin beds each. The house has three full bathrooms (2 up, 1 down), a brand new kitchen with all new appliances, and a dining area which seats 8-10 people comfortably. You will also find a large living room with a gas fireplace, a separate sitting room, a laundry room, and several closets. Cable TV, wireless internet, and a land line phone are included. The house is located just a short distance from Main Street, Great Barrington. It is convenient to Tanglewood, Norman Rockwell Museum, Berkshire Theater Festival, swimming, and all Berkshire attractions. It is close to South Egremont and Sheffield for antique hunters. It is 1/2 a mile from Egremont Country Club which is open to the public for lunch or golf. It is also 5 miles to Catamount and 5 1/2 miles to Butternut Basin for skiers of all ages.

- "Lovely home in a great location which fit our needs well. It was in great condition and quite comfortable.Wish we had more time to enjoy as there is so much to do in the area." - "The house in Great Barrington is charming, comfortable, convenient to all, and very well-stocked with all the essentials you need for a great stay in the Berkshires. We would gladly return the next time we are in the area." - "Have stayed at Marianne’s house before and would 10 stars if that was an option!"

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.

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

Welcome to Moose Lodge – A 7,500 Sq. Ft. Berkshires Luxury Retreat

Experience the pinnacle of comfort and entertainment at Moose Lodge, a stunning 7,500 sq. ft. retreat nestled in the heart of the Berkshires. Perfect for gathering with friends and family, this expansive property offers an abundance of space, luxurious amenities, and a secluded location while keeping you close to vibrant local communities and attractions.

Why You’ll Love Moose Lodge:
Expansive Living Space: Spread out and relax in 7,500 sq. ft. of thoughtfully designed interiors, perfect for both quiet moments and lively gatherings.
Fully Appointed Outdoor Cooking Area: A chef’s dream with everything you need to prepare and enjoy meals al fresco.
Entertainment for Everyone:
Home Theater: A state-of-the-art space for cozy movie nights.
Game Room: Enjoy a billiards table, foosball, poker table, and blackjack table—perfect for hours of fun and friendly competition.
Luxurious Bedrooms: Rest and recharge in plush, comfortable accommodations with serene views.
Outdoor Bliss: Relax on the spacious patio, take in the fresh air, and enjoy evenings by the fire pit under the stars.
The Perfect Berkshires Location:
Nature’s Playground: Explore nearby hiking trails, lakes, and scenic drives, all just steps away from Moose Lodge.
Cultural Gems: Minutes from charming towns with farm-to-table dining, boutique shops, and iconic attractions like Tanglewood and the Norman Rockwell Museum.
With its sprawling 7,500 sq. ft. layout, Moose Lodge is ideal for creating unforgettable memories. Whether you’re enjoying a movie in the theater, competing in the game room, or dining under the stars, this luxurious retreat has everything you need for the perfect escape.

Book your stay at Moose Lodge today and let the adventure begin!

- "We had a wonderful stay at Moose lodge. We had a family wedding and this just made our weekend even better. We love the house and we love Wendy!!!" - "This was the perfect stay for our work retreat!!! Wendy took care of everything - tons of communication, literally everything you need to entertain / cook / hang out. The amenities are stunning - the theater and game room was a highlight for the 15 of us. And the Moose theme is so cool! Couldn’t recommend enough :)"

16 miles from Cranwell Spa & Golf Club in New Marlborough, Rustic Berkshires Cottage at Lake Buel with Kayaks! offers accommodations with access to a spa center. This vacation home features accommodations with a patio. Free Wifi is available throughout the property and Norman Rockwell Museum is 13 miles away. The air-conditioned vacation home is composed of 1 separate bedroom, a living room, a fully equipped kitchen with an oven and microwave, and 1 bathroom. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Tanglewood Musical Center is 16 miles from the vacation home, while Tanglewood is 16 miles from the property. Bradley International Airport is 42 miles away.

- "better then expected" - "Would go back in a heartbeat!"

This apartment is located in a renovated barn on a large private estate, centrally located in the heart of the Berkshires, on fifty acres of beautifully landscaped farming land. The property has a large pond, woodland trails, and abuts onto Beartown Forest with large boating lake and picnic areas. It is located less than five miles from Stockbridge and Great Barrington town centers, and ten miles drive from Lenox and Tanglewood.

The apartment consist of living-room, Kitchen, 1 bedroom with a full size bed and a full size sofa bed, and 1 bathroom.

Minutes drive to restaurants, shops, art galleries and other local attractions including: The Berkshire Theater, Barrington Stage, Shakespeare and Company, Jacob's Pillow, Norman Rockwell Museum, Mass MOCA, Berkshire Botanical Garden, Hancock Shaker Village, Edith Wharton 'The Mount' and other cultural venues.

Year-round outdoor activities include hiking, biking, canoeing, golfing, nature tours, and historic house tours. Winter activities include skiing at Butternut Basin, Catamount Mountain, and Jiminy Peak.

- "I'm never staying anywhere else again when I come to the Berkshires for Tanglewood, etc. The apartment was immaculate and well-equipped, and it's elegant and cozy at the same time. The property is so gorgeous that even the lovely photos don't do it justice. It's pin-drop quiet yet a short drive from both downtown GB and Beartown State Park. A magical place!" - "This charmingly renovated stable, is advertised as being on a 50 acre farm. Truth is, it sits on a baronial estate, complete with hilltop Manor, house, orchards, pond and large greenhouse filled with flowers for the well manicured grounds. Our most lasting memory was sipping wine while sitting in, the Adirondack chairs overlooking the pond and watching swallows swoop down for their evening meal of floating insects."

Cozy Great Barrington Home about 1 Mi to Ski Resort! is located in Great Barrington, just 14 miles from Cranwell Spa & Golf Club and 14 miles from Tanglewood Musical Center. This vacation home provides accommodations with a patio. Free Wifi is available throughout the property and Norman Rockwell Museum is 11 miles away. The air-conditioned vacation home is composed of 4 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. Towels and bed linen are featured in the vacation home. For added privacy, the accommodation features a private entrance. Tanglewood is 14 miles from the vacation home, while Great Falls is 16 miles away. Bradley International Airport is 43 miles from the property.

Accessibility • Child Friendly • Security/Safety • Fireplace/Heating • Internet • Guest Services • Other • Parking

Don't hesitate reach out about availability even if dates look unavailable. We are happy to review avails with you.

A working farm located on more than 1000 feet of the Green River. Over 160 acres of beautiful woods and agricultural fields. Large indoor gymnasium with full basketball court, also good for indoor skating and roller blading. Babbling stream with pond right out the side door. A summer time wonder—but close to the local mountains for ski season.

No weddings, parties, or events.

- "We were a family of 6 adults with an 11 year old. The house is very large and comfortable. There is a lot of space to relax and read our work on a puzzle or project. The grounds are lovely with a nice path cut through the wildflower field. The owners are very responsive and wonderful to work with. Would highly recommend this house." - "We had a beautiful weekend with old friends and family. Lots of space for hanging out both inside and out. The river was a wonderful source of fun and cooking off, bring tubes! Nick was fantastic regarding communication and trip planning. Looking forward to next time!"