Great Barrington Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Great Barrington vacation rentals

Fridge, microwave, oven, stovetop

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is CA $220
CA $367 total
includes taxes & fees
Mar 2 - Mar 3
Home in Great Barrington
Interior

Vacation Home in Great Barrington

Family Ski Getaway in the Berkshires
9.0 out of 10, Wonderful, (11 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is CA $277
CA $430 total
includes taxes & fees
Mar 1 - Mar 2
Family Ski Getaway in the Berkshires
TV, fireplace, printers

Vacation Home in Great Barrington

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (3 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 CA $778
CA $1,818 total
includes taxes & fees
Feb 27 - Feb 28
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Smart TV, DVD player, books, stereo

Vacation Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is CA $390
CA $713 total
includes taxes & fees
Mar 1 - Mar 2
Great Barrington Get Away
3 bedrooms, iron/ironing board, WiFi, bed sheets

Vacation Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
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 CA $465
CA $800 total
includes taxes & fees
Mar 1 - Mar 2
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Dining

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is CA $253
CA $440 total
includes taxes & fees
Mar 3 - Mar 4
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

Mobile Home in Chatham

BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is CA $258
CA $446 total
includes taxes & fees
Mar 10 - Mar 11
BLUSH: Boutique TINY home*private spa*walk to town
Exterior

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (137 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
The price is CA $178
CA $199 total
includes taxes & fees
Mar 1 - Mar 2
Micosta Leisure Inn
Dining

Cottage in Stottville

Pet-Friendly Hudson Escape w/ Hot Tub
The price is CA $232
CA $426 total
includes taxes & fees
Mar 1 - Mar 2
Pet-Friendly Hudson Escape w/ Hot Tub
Interior

Cabin in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is CA $547
CA $961 total
includes taxes & fees
Mar 2 - Mar 3
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Vacation Home in Russell

Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is CA $246
CA $467 total
includes taxes & fees
Mar 6 - Mar 7
Big farmhouse in the foothills of the Berkshires
Property grounds

Vacation Home in Hudson

All the comforts of home
9.2 out of 10, Wonderful, (29 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
The price is CA $145
CA $193 total
includes taxes & fees
Feb 27 - Feb 28
All the comforts of home
Property grounds

Apartment in Hudson

All comforts of home
9.6 out of 10, Exceptional, (54 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is CA $134
CA $181 total
includes taxes & fees
Mar 1 - Mar 2
All comforts of home
House (3 Bedrooms) | Interior

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
The price is CA $268
CA $757 total
includes taxes & fees
Mar 1 - Mar 2
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior detail

Vacation Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
The price is CA $246
CA $417 total
includes taxes & fees
Mar 2 - Mar 3
3-bedroom house in beautiful Berkshires, close to amenities!
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is CA $217
CA $276 total
includes taxes & fees
Mar 1 - Mar 2
The Brooks Motel: Exceptional Suite
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is CA $351
CA $741 total
includes taxes & fees
Mar 23 - Mar 24
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Apartment in Salisbury

Dugway Hideaway Walking Distance to Lime Rock Park
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is CA $274
CA $431 total
includes taxes & fees
Mar 1 - Mar 2
Dugway Hideaway Walking Distance to Lime Rock Park
Exterior

Vacation Home in Stockbridge

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (34 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is CA $409
CA $889 total
includes taxes & fees
Mar 2 - Mar 3
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Outdoor pool, a heated pool

Vacation Home in Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
9.8 out of 10, Exceptional, (30 reviews)
"The home was as described. Exceptional. It was immaculate and well stocked."
United States
judy h.
The price is CA $827
CA $1,510 total
includes taxes & fees
Mar 3 - Mar 4
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
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
"Overall pleasant stay; great facilities, staff, and location"
Casey 2-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Find out more about Great Barrington

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Great Barrington. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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?

Family Ski Getaway in the Berkshires: This highly rated vacation home rental in Great Barrington is located on a river and has a fireplace, a garden, and laundry facilities 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Great Barrington are Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut! and 5 Minutes from Catamount Ski Area.

How many vacation rentals are there in Great Barrington?

With 106 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 Housatonic River are a couple of picturesque spots to enjoy the outdoors. Lake Mansfield Park and Great Barrington Historical Society & Museum 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.