Great Barrington Holiday Rentals

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Holiday 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
Micosta Leisure Inn
Balcony
Micosta Leisure Inn
3.0 star property
9.2 out of 10, Wonderful, (89)
"Great! Had everything you could need and a great view of you wanna sit outside! Very friendly and handsome kitty walking around!!! Thank you!"
The price is HK$899
HK$971 total
includes taxes & fees
25 Nov - 26 Nov
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 HK$1,113
HK$1,721 total
includes taxes & fees
25 Nov - 26 Nov
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 HK$1,494
HK$2,781 total
includes taxes & fees
20 Dec - 21 Dec
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
Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library
Fridge, microwave, oven, stovetop
Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library
9.6 out of 10, Exceptional, (84)
"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."
Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library
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
1 bedroom, premium bedding, pillow-top beds, desk
Quality Inn
2.5 star property
8.2 out of 10, Very good, (1030)
"The young man who worked the Saturday evening shift until 11 ,was a true gentleman "
The price is HK$554
HK$619 total
includes taxes & fees
5 Dec - 6 Dec
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Premium bedding, pillow-top beds, in-room safe, desk
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 HK$918
HK$1,026 total
includes taxes & fees
3 Dec - 4 Dec
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 HK$1,183
HK$1,321 total
includes taxes & fees
25 Nov - 26 Nov
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 holiday rental in Great Barrington?

Yes, there are holiday rentals close to the most popular sights in Great Barrington, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and live music in Great Barrington. Leave some time to check out the ski slopes and theatre scene during your trip.

What are some of the best holiday rentals that Great Barrington has to offer?

Private Estate, Heated YEARROUND Outdoor Pool: This highly rated holiday 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 that you can cook with friends or family. Make the most of books in this rental home to help you unwind. Our travellers also rate Lakefront Berkshires Retreat w/ Deck, Dock & Boat! as a favourite home for rent in Great Barrington.

How many holiday rentals are there in Great Barrington?

With 92 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Great Barrington?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Great Barrington. Holiday rentals offer amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family trips.