Great Barrington holiday rentals

We found 686 holiday rentals — enter your dates for availability
Discover a selection of 96 homes, 12 apartments and other holiday rentals in Great Barrington that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, including Wi-Fi and parking. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Great Barrington

Showing deals for:13 Nov - 20 Nov

Queen bedroom
Terrace/patio
Dining room with butcher block table
Screened in porch
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,773
for 7 nights, 1 home
AU$539 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Living area
Interior
Pool
Interior
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,423
for 7 nights, 1 home
AU$632 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Dining
The great room with wonderful water views and working fireplace
Open kitchen to great room, wonderful for cooking and entertaining
Hot tub overlooking the lake
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
AU$6,608
for 7 nights, 1 home
AU$944 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Living area
Exterior
Interior
Room
Exceptional
(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
AU$6,331
for 7 nights, 1 home
AU$904 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
kitchen
Brand new hot tub with privacy gazebo. Imagine soaking in this lovely hot tub, where all cares can bubble away.
private entrance
Living area
Exceptional
(76 reviews)

A fun country escape for two! featuring a fireplaces,hot tub, and ping pong

Sandisfield

8% off
AU$4,659
for 7 nights, 1 room
AU$666 per night
includes taxes & fees
A fun country escape for two! featuring a fireplaces,hot tub, and ping pong
Outdoor dining
Kitchen with counter seating for 4- door on the right to garage
View from entry into living room- perfect spot for relaxing!
Enclosed porch- view into back yard- dining/game table
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
AU$5,431
for 7 nights, 1 home
AU$776 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Welcome Home!
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Back patio with Hot Tub
Unwind and cherish moments together in the inviting warmth of the cozy living room.
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
AU$7,655
for 7 nights, 1 home
AU$1,094 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Exterior
Interior
Living area
Dining
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,869
for 7 nights, 1 cabin
AU$553 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
A mudroom off the back leads to the large wooden deck
You will love dining and working in this rich and colorful room
Outdoor dining and grill on the 16' x 20' wooden deck.
Staircase
Exceptional
(41 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$4,700
for 7 nights, 1 home
AU$671 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Dining Area view
View from the Top Deck
Approaching the home
View from the water
Exceptional
(10 reviews)

Lakefront +pets +skiing +bbq +firepit +games

Copake

8% off
AU$3,713
for 7 nights, 1 home
AU$530 per night
includes taxes & fees
Lakefront +pets +skiing +bbq +firepit +games
2 car garage—ping pong and bikes.
You, the moon, the fire pit…..,
Flat screen Smart cable tv 5G network. WiFi of course.
Dining
Exceptional
(191 reviews)

“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

Sheffield

8% off
AU$3,070
for 7 nights, 1 home
AU$439 per night
includes taxes & fees
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
Exterior
Private kitchen
Living area
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Sheffield

8% off
AU$9,289
for 7 nights, 1 home
AU$1,327 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Kitchen
Kitchen
East end
Dining room
Exceptional
(51 reviews)

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington

8% off
AU$4,964
for 7 nights, 1 home
AU$709 per night
includes taxes & fees
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Front Gardens
Living Room
Property grounds
Kitchen
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

Stockbridge

8% off
AU$4,386
for 7 nights, 1 home
AU$627 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
We highly recommend the Sauna
Property grounds
Interior
After a day in the snow
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
AU$3,514
for 7 nights, 1 home
AU$502 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Living area
Living area
Terrace/patio
Private kitchen
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

7% off
AU$4,123
for 7 nights, 1 home
AU$589 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
Alfresco dining
River view from window
dining area
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
AU$3,547
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Dining Room - table expands to seat 10
Living Room - Queen Sleep Sofa (First Floor)
Kitchen with Dining Area - well-equipped and great layout
Backyard
Exceptional
(10 reviews)

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

9% off
AU$4,126
for 7 nights, 1 home
AU$589 per night
includes taxes & fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lobby
Living area
Interior
Living area
Exceptional
(7 reviews)

The Race Mountain House

Sheffield

35% off
AU$5,411
for 7 nights, 1 home
AU$773 per night
includes taxes & fees
The Race Mountain House
Private kitchen
Room
Outdoor dining
Dining
Exceptional
(32 reviews)

The Hideaway: Berkshire Home - Village of Egremont

egremont

16% off
AU$3,342
for 7 nights, 1 home
AU$477 per night
includes taxes & fees
The Hideaway: Berkshire Home - Village of Egremont
Enjoy a beautiful crisp night under the lights
After a hard day on the trails or a long day on the town, relax in this oasis
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Never miss a thing with this expansive open concept kitchen and living room
Exceptional
(28 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

6% off
AU$5,683
for 7 nights, 1 home
AU$812 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Second story deck with lake views, dining table for 8, sitting area and grill
Open kitchen area with bar seating, great for socializing while you meal prep.
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Open and bright main floor living space with stunning views of Laurel Lake.
Exceptional
(30 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

15% off
AU$5,571
for 7 nights, 1 home
AU$796 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Dining
Terrace/patio
Interior
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
AU$3,442
for 7 nights, 1 cottage
AU$492 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Kitchen
Interior
Property grounds
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,428
for 7 nights, 1 home
AU$775 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The lively city of Great Barrington awaits you

The area's live music and theatre scene are just some of the reasons to come on holiday to Great Barrington. Well known for its rock climbing, hiking and cafes, this scenic city won't disappoint. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Great Barrington

Are you looking for attractions to see during your stay? You'll be sure to enjoy Great Barrington for its hiking and skiing. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Great Barrington a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (2.3 mi / 3.7 km)
  • Catamount Ski Area (6.3 mi / 10.1 km)
  • Umpachene Falls Park (8.4 mi / 13.6 km)
  • Wyndhurst Golf & Club (11.3 mi / 18.1 km)
  • Otis Ridge (13.4 mi / 21.5 km)
  • Kennedy Park (13.4 mi / 21.6 km)

Exploring the natural landscape of Great Barrington

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Great Barrington is a great place to get out in nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Housatonic River Walk (0.1 mi / 0.2 km)
  • Housatonic River (0.1 mi / 0.2 km)
  • Lake Mansfield Park (0.7 mi / 1.1 km)
  • Lake Buel (4.8 mi / 7.7 km)
  • Naumkeag Museum (6.9 mi / 11.1 km)
  • Berkshire Botanical Garden (7.4 mi / 11.8 km)

Seasonal weather averages in Great Barrington

Travellers enjoy Great Barrington for its skiing. To make the most of the cold weather activities, you might consider visiting in January, March, February or November, when snowfall averages 18 cm and temperatures average -2°C.

Transport options to and around Great Barrington

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 16.2 mi (26.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Hudson, NY (HCC-Columbia County), which is 19.2 mi (30.9 km) away.

Frequently asked questions

What is the best area to stay in Great Barrington when booking a holiday home?
One of the more in-demand destinations to choose your Stayz holiday home in Great Barrington is Egremont. Set up home here and enjoy its big-ticket attractions, including Catamount Ski Area and Jug End State Reservatio.
What is the most popular type of holiday home accommodation in Great Barrington?
Houses are the most popular style of holiday home in Great Barrington, according to our data. Even if you've got a different idea in mind, Stayz has properties in many shapes and sizes. Look through our options to find your perfect pad.
How much does it cost to rent a holiday home in Great Barrington?
Different things can determine what you'll pay for your holiday home in Great Barrington, like the type of property, season and length of stay. However, all our holiday homes have one thing in common — amazing value. Just enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Great Barrington?
When you travel and the style and size of the property will influence how much you'll pay for your beachside holiday home. Put in your Great Barrington travel dates to see your options on Stayz. Can't live without a hot tub? Use the filters to pick the features and amenities you want.
Are there pet-friendly holiday homes in Great Barrington?
With 39 properties that host four-legged guests, your happy hound can join in on your Great Barrington getaway. Use our filter tool to browse our pet-friendly holiday homes and find the pawfect pad on Stayz.
Can I rent a house with a pool in Great Barrington?
Grab your swimsuit and pool noodle, because there are four houses with a private pool in Great Barrington. Kick back at one of these popular holiday homes and every day can be a pool day. Simply enter your dates into Stayz, then check the "pool" filter to find the ideal place for a splashing good time!
What are popular home amenities in Great Barrington?
When it comes to home amenities that guests are searching for in Great Barrington, a swimming pool, an electric car charging station and nearby museums rank the highest. With Stayz holiday homes, you'll discover options to suit your style and taste, whether you're going on a trip with your partner, your friends or even pets.
Are there large group holiday homes in Great Barrington?
Great Barrington has six holiday properties that can accommodate 10 or more guests. These stays come with the space and privacy you need to share good times with your favourite people.
Are there holiday homes in Great Barrington that welcome kids?
Bring the entire family together for an unforgettable adventure in Great Barrington at one of our 39 family-friendly holiday homes. Many of these stays come with conveniences that are ideally suited to trips with the kids, such as laundry facilities, extra bedrooms and outdoor spaces. Just check the "Properties good for families" filter and choose your favourite option.
What are the top attractions for families in Great Barrington?
Keep your kids busy at these fantastic family-friendly attractions in Great Barrington:
  • Umpachene Falls Park
  • Norman Rockwell Museum
  • Bash Bish Falls State Park
Are there one-bedroom holiday homes in Great Barrington?
Yes, you can pick from three one-bedroom homes in Great Barrington. Whether you want a cosy cottage or an upmarket condo, Stayz's one-bedroom homes are ideal if you don't require lots of room. One of the best things about having your own place? You won't ever have to share your holiday with strangers.
Can I find two-bedroom holiday homes in Great Barrington?
Gather your loved ones and enjoy total privacy and comfort in one of the 10 two-bedroom holiday properties Great Barrington has to offer.
Are there holiday homes with WiFi in Great Barrington?
Great Barrington has 12 holiday homes with WiFi, so you'll be able to stay connected while you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to checking emails, these Stayz homes make it easy to get online.
How can I find holiday homes with air conditioning in Great Barrington?
Work out your travel dates and then use our filter tool to see holiday homes with ac in Great Barrington on Stayz. With 34 air-conditioned properties to choose from here, you can enjoy a comfy and cool stay.
How old do you have to be to rent a holiday home in Great Barrington?
Age restrictions can differ across properties on Stayz, so look at the rules of the holiday home in Great Barrington you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Great Barrington for?
The length of time you can rent a holiday home in Great Barrington depends on the property. Just enter your selected dates to view a list of options offering extended stays. With plenty of features like washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to discover a terrific place to call your home away from home in Great Barrington.

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