Great Barrington Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Great Barrington holiday rentals

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, (4 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$4,436
HK$10,409 total
includes taxes & fees
2 May - 3 May
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,586
HK$2,516 total
includes taxes & fees
4 May - 5 May
Home in Great Barrington
Interior

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (26 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
The price is HK$2,311
HK$5,784 total
includes taxes & fees
13 May - 14 May
Modern Victorian Walk to Main Street
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$2,350
HK$4,182 total
includes taxes & fees
3 May - 4 May
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,586
HK$2,481 total
includes taxes & fees
5 May - 6 May
Cozy Riverside Berkshires Retreat
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (142 reviews)
"Steven is the most helpful and kind host I've ever experienced! The property is lovely, and the rooms are cozy. I would definitely recommend staying here especially as a solo traveler."
United States
Salvio
The price is HK$1,018
HK$1,140 total
includes taxes & fees
8 May - 9 May
Micosta Leisure Inn
Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is HK$1,535
HK$4,337 total
includes taxes & fees
2 May - 3 May
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (145 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is HK$1,449
HK$2,699 total
includes taxes & fees
3 May - 4 May
Big farmhouse in the foothills of the Berkshires
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$768
HK$1,036 total
includes taxes & fees
3 May - 4 May
All comforts of home
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$1,410
HK$3,334 total
includes taxes & fees
3 May - 4 May
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (36 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is HK$2,812
HK$5,687 total
includes taxes & fees
4 May - 5 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Dining

Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub
Stottville
The price is HK$1,329
HK$2,419 total
includes taxes & fees
4 May - 5 May
Pet-Friendly Hudson Escape w/ Hot Tub
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,856
HK$3,946 total
includes taxes & fees
13 May - 14 May
Cheerful 3-bedroom cottage with woodstove
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is HK$4,230
HK$6,858 total
includes taxes & fees
3 May - 4 May
Whispering Estate Guest House - A Romantic Countryside Getaway
Smart TV, books

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
The price is HK$1,255
HK$3,090 total
includes taxes & fees
4 May - 5 May
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$3,721
HK$6,685 total
includes taxes & fees
28 May - 29 May
Spacious 5-bedroom house in charming Lee with WiFi
Fridge, microwave, oven, stovetop

A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is HK$6,972
HK$11,538 total
includes taxes & fees
4 May - 5 May
A Country Lodge Straight Out of the Pages of a Great Novel
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is HK$2,100
HK$4,415 total
includes taxes & fees
5 May - 6 May
Treetop Hideaway in Tyringham
Fridge, microwave, oven, stovetop

Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape
Stottville
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$1,305
HK$2,387 total
includes taxes & fees
6 May - 7 May
Hudson Hot Tub & Pet Escape
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The room and the stay was incredible. The kitchen was fully stocked. I would just suggest maybe serving breakfast "
dana 2-night trip
Posted 7 hours ago
Berkshire Mountain Lodge

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:

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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 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. Our travellers also rate Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut! as a favourite home for rent in Great Barrington.

How many holiday rentals are there in Great Barrington?

With 106 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.