Great Barrington Vacation Rentals

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Vacation Rentals in Great Barrington

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Interior
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Private Estate, Heated YEARROUND Outdoor Pool
Fridge, microwave, oven, stovetop
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (13)
"The country setting provided a quiet retreat. The home is well equipped: plenty of beds, multiple gathering places, pool with towels (although it was pretty cold until the pool guy came and provided help). The outdoor grill provides additional cooking space. The home is within easy driving to many places of interest. We had a nice week at this home."
Private Estate, Heated YEARROUND Outdoor Pool
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Perfect Vacation Get Away - Historical New Marlborough
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.4 out of 10, Exceptional, (54)
"It was a pleasure to find this gem of a cabin available for a night so we could attend a concert at Tanglewood, despite living out of state. The location was lovely, convenient and quiet; the cabin was impeccably appointed (thanks for the fresh flowers in every room and bottle of Riesling!) and very clean with every possible amenity; and the hosts were communicative, friendly and helpful. Overall, this was an idyllic mix of quaint/cute/unique and function/comfort/ease. I will absolutely seek out...
Perfect Vacation Get Away - Historical New Marlborough
Peaceful, Post and Beam Loft, Sleeps 9
1 bedroom, iron/ironing board, WiFi, bed sheets
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (14)
"House and grounds are large! Firepit is great! Local hiking and restaurants were fantastic! Enjoyed the large rooms and decor and artworks and prints."
Peaceful, Post and Beam Loft, Sleeps 9
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
7 bedrooms, free WiFi, bed sheets
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
10.0 out of 10, Exceptional, (25)
"It was a quirky and interesting house!"
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Great Barrington Get Away
Fridge, microwave, oven, stovetop
Great Barrington Get Away
9.2 out of 10, Wonderful, (22)
"Well-located home, comfortable home with a well-stocked kitchen and plenty of space. We hope to return! "
The price is CA $382
CA $707 total
includes taxes & fees
Nov 25 - Nov 26
Great Barrington Get Away
Micosta Leisure Inn
Balcony
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (88)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is CA $157
CA $169 total
includes taxes & fees
Nov 17 - Nov 18
Micosta Leisure Inn
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (220)
"A quick weekend! Repeat guests! Place is always immaculate- and easy check in/check out. "
The price is CA $199
CA $306 total
includes taxes & fees
Nov 18 - Nov 19
Berkshire Village Carriage House - Super Private!!
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (208)
"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
9.8 out of 10, Exceptional, (37)
"Beautiful property located in the woods with plenty of privacy. 3 floors with a lot of elbow room and a tennis court also! Very good communication with the owners with easy check in/check out instructions. "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (195)
"My husband and I loved our stay there.. The house was very clean with a beautiful scenic back yard. Enjoyed the porch and the view of the lake. Easy check in and check out.. I would highly recommend this place."
Peace and quiet on the lake
Serene Acreage - Pond - Hiking Trails Nearby
Terrace/patio
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (6)
"Wonderful accommodation."
Serene Acreage - Pond - Hiking Trails Nearby
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (9)
"Enjoyed the foliage and some nice hikes. House was comfortable and clean. Owner was responsive and helpful. We arrived at night and had trouble locating the property when our gps failed. Owner was helpful guiding us to the house. I suggest arriving in the light of day. "
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshire Lake access
Lake
Berkshire Lake access
10.0 out of 10, Exceptional, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access
The Meadows House @ Otis Ridge w/ 7-person hot tub
Outdoor spa tub
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (24)
"We stayed at the Meadow House over Labor Day weekend. Lars was super accommodating to us and made sure we were taken care of. Really quick responses from him and he’s even working with us to return something one of the friends I was with left behind. Definitely recommend this house if you’re looking to escape the city or go hiking near by."
The Meadows House @ Otis Ridge w/ 7-person hot tub
Quintessential 6-BR Berkshires Lodge
Exterior
Quintessential 6-BR Berkshires Lodge
9.8 out of 10, Exceptional, (8)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge
Cheerful 3-bedroom cottage with woodstove
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (29)
"Sabrina saw to everything. The house even came equipped with a spice drawer, games like badminton equipment, a kid’s bedroom with games and books, and nice touches like vases of flowers. Our family was amazed and impressed. The outdoor area in the front (and back) was big enough for our grandchildren to play badminton. We very highly recommend this place!"
The price is CA $329
CA $702 total
includes taxes & fees
Nov 6 - Nov 7
Cheerful 3-bedroom cottage with woodstove
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.
9.8 out of 10, Exceptional, (16)
"Clean, house has plenty of room. Lovely property. "
Amore Estate - beautiful room with many places to explore and relax in.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Great Barrington you may be interested in

Quality Inn
Standard Room, 2 Queen Beds, Non Smoking
Quality Inn
2.5 star property
8.2 out of 10, Very good, (1001)
"Great location, within a short walk to Greater Barrington. Room is clean and breakfast was good. A few areas could use some upkeep."
The price is CA $99
CA $111 total
includes taxes & fees
Nov 19 - Nov 20
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Standard Room
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (560)
"The holiday inn express was very clean and comfortable"
The price is CA $164
CA $183 total
includes taxes & fees
Nov 20 - Nov 21
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.2 out of 10, Wonderful, (671)
"Great hotel with nice staff and facilities. Close to grocery, restaurants and Stockbridge tourist attractions."
The price is CA $188
CA $210 total
includes taxes & fees
Nov 7 - Nov 8
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a vacation rental in Great Barrington?

Yes, there are vacation rentals close to the most popular points of interest in Great Barrington, or you can select a secluded option if you're looking for relaxation. Visitors like the top-notch restaurants and live music in Great Barrington. Leave some time to check out the ski slopes and theater scene during your trip.

What are some of the best vacation rentals in Great Barrington?

Private Estate, Heated YEARROUND Outdoor Pool: This highly rated vacation home rental in Great Barrington offers a balcony, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind. Our travelers also rate Lakefront Berkshires Retreat w/ Deck, Dock & Boat! as a favorite home for rent in Great Barrington.

How many vacation rentals are there in Great Barrington?

With 91 Expedia vacation rentals, you're sure to find just the right place for your Great Barrington stay.

What can I see and do in Great Barrington?

Cultural attractions include Mahaiwe Performing Arts Center and Art et Industrie, whereas Housatonic River Walk and Housatonic River are a couple of picturesque spots to enjoy the outdoors. Ski Butternut and Lake Buel are other places to visit while you're in town.

What are vacation rentals like in Great Barrington?

Vacation rentals are privately owned properties you can reserve for several days or more in Great Barrington. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family getaway.