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 $420
CA $759 total
includes taxes & fees
Dec 3 - Dec 4
Great Barrington Get Away
Micosta Leisure Inn
Balcony
Micosta Leisure Inn
3.0 star property
9.2 out of 10, Wonderful, (89)
"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 $161
CA $174 total
includes taxes & fees
Nov 25 - Nov 26
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, (225)
"One of the best properties i've ever stayed at "
The price is CA $200
CA $309 total
includes taxes & fees
Nov 25 - Nov 26
Berkshire Village Carriage House - Super Private!!
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
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
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
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, (209)
"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
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!
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
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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
Private Island - Largest Fresh Water Reservoir in Mass....
Outdoor dining
Private Island - Largest Fresh Water Reservoir in Mass....
9.0 out of 10, Wonderful, (7)
"From beginning to end, could not have dreamed of a better island getaway, in the Berkshire’s none-the -less. Bill was a wonderful host. Very friendly, responsive and helpful. Super welcoming. The home was simple, quaint, and super cozy. Perfect for a nice long relaxing weekend for both the dogs and people. The views from the sun room were lovely. The deck/patio area had a beautiful view of the water. The fire pit was a nice perk in the evening. Surrounded by water, the place felt so private....
Private Island - Largest Fresh Water Reservoir in Mass....
Big farmhouse in the foothills of the Berkshires
Property grounds
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (128)
"Our stay was wonderful. Host was great with communication. We arrived in the evening, all the lights were on and pellet stove running for us. "
The price is CA $268
CA $499 total
includes taxes & fees
Dec 20 - Dec 21
Big farmhouse in the foothills of the Berkshires
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
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, (1050)
"The young man who worked the Saturday evening shift until 11 ,was a true gentleman "
The price is CA $99
CA $111 total
includes taxes & fees
Dec 8 - Dec 9
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, (564)
"Look clean, great staffs."
The price is CA $165
CA $184 total
includes taxes & fees
Dec 3 - Dec 4
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, (672)
"Great hotel with nice staff and facilities. Close to grocery, restaurants and Stockbridge tourist attractions."
The price is CA $212
CA $237 total
includes taxes & fees
Nov 25 - Nov 26
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.
Beautiful view of the beach with palm trees

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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 92 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 Lake Mansfield Park 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.