A large stone church with a tall bell tower and arched windows.

Great Barrington Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Great Barrington holiday rentals

Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is HK$2,118
HK$3,189 total
includes taxes & fees
29 Jul - 30 Jul
Home in Great Barrington
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (20 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is HK$1,870
HK$2,843 total
includes taxes & fees
10 Aug - 11 Aug
Cozy Riverside Berkshires Retreat
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (6 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,461
HK$10,440 total
includes taxes & fees
6 Aug - 7 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Coffee/tea maker, fridge, microwave, oven

Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.0 out of 10, Very good, (1 review)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is HK$812
HK$1,213 total
includes taxes & fees
9 Aug - 10 Aug
Cozy 1-bedroom studio in serene Great Barrington with AC
TV, fireplace, stereo

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (50 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
The price is HK$9,619
HK$15,591 total
includes taxes & fees
2 Aug - 3 Aug
Great Barrington, Cabin Sleeps 14, Walk To Town
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,027 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is HK$943
HK$1,228 total
includes taxes & fees
26 Aug - 27 Aug
Berkshire Mountain Lodge
Outdoor dining

Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood

Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood
New Lebanon
The price is HK$3,621
HK$6,278 total
includes taxes & fees
29 Jul - 30 Jul
Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood
TV, fireplace, DVD player, books

Hudson Valley Multi-Unit Escape: Secluded + Scenic

Hudson Valley Multi-Unit Escape: Secluded + Scenic
Claverack
Hudson Valley Multi-Unit Escape: Secluded + Scenic
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (8 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is HK$1,765
HK$2,978 total
includes taxes & fees
2 Aug - 3 Aug
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (159 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is HK$1,087
HK$1,217 total
includes taxes & fees
3 Aug - 4 Aug
Micosta Leisure Inn
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (13 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is HK$3,137
HK$5,510 total
includes taxes & fees
29 Jul - 30 Jul
Guesthouse Cabin vacation rentals in Berkshire County
Beach nearby

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
The price is HK$2,470
HK$4,660 total
includes taxes & fees
6 Aug - 7 Aug
Beachwood Cottage
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is HK$2,784
HK$5,256 total
includes taxes & fees
26 Aug - 27 Aug
Treetop Hideaway in Tyringham
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,176
HK$1,493 total
includes taxes & fees
28 Jul - 29 Jul
The Brooks Motel: Exceptional Suite
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is HK$1,694
HK$3,452 total
includes taxes & fees
28 Jul - 29 Jul
stylish Berkshires Retreat
Coffee/tea maker, fridge, microwave, stovetop

Berkshire House Stay: 5BR/5BA

Berkshire House Stay: 5BR/5BA
Lee
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
Berkshire House Stay: 5BR/5BA
Exterior

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is HK$2,294
HK$4,282 total
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature
Smart TV, books

Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is HK$2,878
HK$5,379 total
includes taxes & fees
26 Aug - 27 Aug
Spacious Central Berkshires Home for Groups
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is HK$1,804
HK$2,978 total
includes taxes & fees
28 Jul - 29 Jul
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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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Top Great Barrington Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"There were no amenities but breakfast, which was absolutely adequate. The staff was very helpful, parking easy and the room was comfortable with good showers. The water pressure needed some help and a hair dryer would have been helpful but all in all the location made up for it."
Joanna 2-night trip
Posted 19 hours ago
Quality Inn Great Barrington

Find out more about Great Barrington

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:

  • View our selection of featured holiday rentals in Great Barrington
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  • Enter your travel dates to view the best deals on holiday rentals in Great Barrington while they last

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 in Great Barrington close to Mahaiwe Performing Arts Center, 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?

Cozy Riverside Berkshires Retreat: This highly rated holiday home rental in Great Barrington is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Great Barrington?

With 98 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?

Housatonic River Walk and Housatonic River are a couple of scenic spots to enjoy the outdoors, whereas Art et Industrie is one of the cultural attractions. Mahaiwe Performing Arts Center and Lake Mansfield Park 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.