Great Barrington Holiday Rentals

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Holiday Rentals in Great Barrington

The Freeman - Newly Renovated 14K SF Estate on 40 Acres
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Moose Lodge by AvantStay | Luxe Berkshires Escape
Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
"It was unique, with unusual amenities, like the home theater and fabulous game room. Our weather was wintery, so this was such a comfortable and fun way for the family to spend time together!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
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, (39)
"This house was the perfect get away house for out family! The place was clean and the kitchen well stocked! We had wonderful large family dinners and enjoyed heading into town for meals and fun too. We had the best hikes with are wonderful dog that we got to include, it was a very special week. Great location and the most peaceful and amazing views from the deck and the dock. Would stay here again for sure! Thank you for sharing your home."
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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Perfect Vacation Get Away - Historical New Marlborough
Property grounds
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is HK$1,172
per night
6 May - 7 May
Perfect Vacation Get Away - Historical New Marlborough
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, (23)
"Interesting and lovely! We had a great time and the hosts were very welcoming and responsive"
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Peace and quiet on the lake
Interior
Peace and quiet on the lake
9.6 out of 10, Exceptional, (182)
"We loved our two night stay in the forest :) The house was super clean, well appointed, quiet and relaxing. We didn't have great weather so didn't get to take advantage of the perfect spot on the lake or any of the kayaks or boats, but the location was a great jumping off point for visiting the various Berkshires towns."
Peace and quiet on the lake
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"
Berkshire Village Carriage House - Super Private!!
Micosta Leisure Inn
Balcony
Micosta Leisure Inn
3.0 star property
8.8 out of 10, Excellent, (70)
"I needed a place to sleep while attending several events in the area and this was perfect; clean, safe, warm, great snacks. The only negative was the icy steps and deck. I had to break up the ice and clear with my boots. Place could use an electric kettle for tea. Other than that it was a great place for me and my elderly dog. "
The price is HK$980
per night
5 May - 6 May
Micosta Leisure Inn
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, (195)
"The house is beautifully remodeled and clean. Nice open area with all like new kitchen appliances. My friend and I are thinking of going back in the summer to enjoy the lake"
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Pristine Home In Becket Woods
Fridge, microwave, oven, stovetop
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...
Pristine Home In Becket Woods
Fox Hollow Luxury Ranch Laurel Lake
Fridge, microwave, oven, stovetop
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
"Generous facility, nicely located, accommodating host."
Fox Hollow Luxury Ranch Laurel Lake
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Stockbridge Home, Come Experience The Berkshires!
Fridge, microwave, oven, stovetop
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (10)
"The hosts have made this ranch house into an artsy, cozy place for families to rest and relax! Plenty of space for family hang outs and game playing, but also enough rooms for tweens or teens to get away and have alone time. Beautiful spaces throughout. We would have loved to enjoy the backyard space and screened-in porch if it hadn't been winter, but appreciated watching the snow falling while sipping coffee by the kitchen window! Close to Catamount ski area and minutes from Stockbridge shops...
Stockbridge Home, Come Experience The Berkshires!
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
Property grounds
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - On Largest Fresh Water Reservoir in Mass. 24' Pontoon boat
Chic Pittsfield Home With A View!
Property grounds
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."
Chic Pittsfield Home With A View!
Romantic and Secluded Berkshire's Gem
Fridge, microwave, oven, stovetop
Romantic and Secluded Berkshire's Gem
10.0 out of 10, Exceptional, (9)
"My friends and I had an amazing time staying in the cozy cabin. 9 of us slept comfortably, the place was spotless, and so cute. We hope to visit again."
Romantic and Secluded Berkshire's Gem
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Fridge, microwave, oven, stovetop
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Serene Acreage - Pond - Hiking Trails Nearby
Property grounds
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
"Perfect place to relax and have dogs as part of a mini vacation. Very clean, organized, and provided helpful local information. Will definitely stay there again."
Serene Acreage - Pond - Hiking Trails Nearby
Cozy Cabin in the Berkshires
Property grounds
Cozy Cabin in the Berkshires
10.0 out of 10, Exceptional, (3)
"Cant wait to book again. Great place for familys. Owner thinks of everything that you would need during your stay."
Cozy Cabin in the Berkshires
Quintessential 6-BR Berkshires Lodge
Exterior
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."
Quintessential 6-BR Berkshires Lodge
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See all available properties in Great Barrington
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.

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
8.0 out of 10, Very good, (1000)
"Generally a good stay, great value"
The price is HK$626
per night
5 May - 6 May
Quality Inn
Monument Mountain Motel
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (588)
"Easy access, very clean, nearby restaurants "
The price is HK$520
per night
6 May - 7 May
Monument Mountain Motel
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, (645)
"Employees were excellent. Very nice location to stay. Pool was nice and well kept "
The price is HK$1,258
per night
27 May - 28 May
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.

Search for holiday rentals in Great Barrington on Expedia! You can easily find your home rentals, villas, holiday apartments in Great Barrington using one of the methods below:

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Look no further and take a look at our great range of rental properties in Great Barrington!

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.

How many holiday rentals are there in Great Barrington?

With 104 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 Housatonic River are a couple of picturesque spots to enjoy the outdoors. Ski Butternut and Catamount Ski Area 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.

Recent reviews of Great Barrington properties
Expedia verified reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

5/5 Excellent
"Very good. "
A verified traveller stayed at The Yankee, Trademark Collection by Wyndham
Posted 11 hours ago
The Yankee, Trademark Collection by Wyndham