Great Barrington Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Great Barrington vacation 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
$1,193 nightly
The price is $1,332
Apr 1 - Apr 2
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
$270 nightly
The price is $302
Apr 1 - Apr 2
Total with taxes and fees
Cozy Riverside Berkshires Retreat
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
$275 nightly
The price is $307
Apr 23 - Apr 24
Total with taxes and fees
Home in Great Barrington
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.
$461 nightly
The price is $515
Apr 13 - Apr 14
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
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.
$270 nightly
The price is $305
Apr 1 - Apr 2
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
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
$133 nightly
The price is $150
Apr 1 - Apr 2
Total with taxes and fees
Micosta Leisure Inn
House (4 Bedrooms) | Interior

52-acre Berkshires Farmhouse Fire Pit, Outdoor Dining + Trails Copper Kettle Farm by Avantstay

52-acre Berkshires Farmhouse Fire Pit, Outdoor Dining + Trails Copper Kettle Farm by Avantstay
3.0 star property
Ashley Falls
52-acre Berkshires Farmhouse Fire Pit, Outdoor Dining + Trails Copper Kettle Farm by Avantstay
House (3 Bedrooms) | 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
$499 nightly
The price is $554
Apr 1 - Apr 2
Total with taxes and fees
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, (144 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
$322 nightly
The price is $340
Apr 1 - Apr 2
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
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.
$377 nightly
The price is $421
Apr 1 - Apr 2
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Property grounds

3-Bedroom Cabin Getaway With Rustic Charm

3-Bedroom Cabin Getaway With Rustic Charm
Cornwall
8.4 out of 10, Very Good, (6 reviews)
"Absolutely beautiful cottage exactly as pictured inside and out. "
United States
Michaela C.
$476 nightly
The price is $540
Apr 1 - Apr 2
Total with taxes and fees
3-Bedroom Cabin Getaway With Rustic Charm
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, (35 reviews)
"A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!"
United States
Susan
$648 nightly
The price is $724
Apr 1 - Apr 2
Total with taxes and fees
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
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.
$614 nightly
The price is $686
Apr 1 - Apr 2
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
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
$118 nightly
The price is $132
Apr 1 - Apr 2
Total with taxes and fees
All comforts of home
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.
$452 nightly
The price is $505
Apr 1 - Apr 2
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$677 nightly
The price is $699
Apr 1 - Apr 2
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Dining

Whispering Estate Guest House - Countryside Getaway

Whispering Estate Guest House - Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
$780 nightly
The price is $884
Apr 1 - Apr 2
Total with taxes and fees
Whispering Estate Guest House - Countryside Getaway
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.
$715 nightly
The price is $798
Apr 7 - Apr 8
Total with taxes and fees
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.
$1,295 nightly
The price is $1,465
Apr 1 - Apr 2
Total with taxes and fees
A Country Lodge Straight Out of the Pages of a Great Novel
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)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
$343 nightly
The price is $383
Apr 1 - Apr 2
Total with taxes and fees
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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
"The Quality Inn in Great Barrington is a good value play. The room we had was clean; the staff was friendly and knowledgeable; and the heating was welcomed on this March day. Breakfast was a weak point, but the coffee was good and available throughout the day. And yes, I would stay there again. "
Leslie 1-night trip
Posted 13 hours ago
Quality Inn Great Barrington

Find out more about Great Barrington

Everything you need to know about Great Barrington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Great Barrington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Great Barrington vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Great Barrington vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Great Barrington. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Great Barrington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Great Barrington rentals

At Expedia, we put the best Great Barrington vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Great Barrington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Great Barrington vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Great Barrington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Great Barrington?

Yes, there are vacation rentals in Great Barrington close to Mahaiwe Performing Arts Center, or you can select a more secluded option if you'd like a relaxing place to stay. 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?

Cozy Riverside Berkshires Retreat: This highly rated vacation 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 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. Our travelers also rate Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut! as a favorite home for rent in Great Barrington.

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?

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 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.