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

Property grounds
Terrace/patio
Dining room with butcher block table
Queen bedroom
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,761
for 7 nights, 1 home
AU$537 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Private kitchen
Interior
Pool
Living area
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,409
for 7 nights, 1 home
AU$630 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Hot tub overlooking the lake
The great room with wonderful water views and working fireplace
Dining
Open kitchen to great room, wonderful for cooking and entertaining
Exceptional
(86 reviews)

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

Lee

8% off
AU$6,587
for 7 nights, 1 home
AU$941 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Room
Exterior
Interior
Living area
Exceptional
(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
AU$6,312
for 7 nights, 1 home
AU$902 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
private entrance
Brand new hot tub with privacy gazebo. Imagine soaking in this lovely hot tub, where all cares can bubble away.
Living area
kitchen
Exceptional
(76 reviews)

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

Sandisfield

8% off
AU$4,645
for 7 nights, 1 room
AU$664 per night
includes taxes & fees
A fun country escape for two! featuring a fireplaces,hot tub, and ping pong
Property grounds
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$5,414
for 7 nights, 1 home
AU$773 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Add a touch of warmth and charm to your dining experience!
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
Welcome Home!
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$7,631
for 7 nights, 1 home
AU$1,090 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Property grounds
Interior
Exterior
Living area
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,857
for 7 nights, 1 cabin
AU$551 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Outdoor dining and grill on the 16' x 20' wooden deck.
You will love dining and working in this rich and colorful room
A mudroom off the back leads to the large wooden deck
The living room flows into the dining room.
Exceptional
(41 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$4,685
for 7 nights, 1 home
AU$669 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
View from the water
View from the Top Deck
Approaching the home
Living area
Exceptional
(10 reviews)

Lakefront +pets +skiing +bbq +firepit +games

Copake

8% off
AU$3,702
for 7 nights, 1 home
AU$529 per night
includes taxes & fees
Lakefront +pets +skiing +bbq +firepit +games
It’s cool on the screened porch
You, the moon, the fire pit…..,
2 car garage—ping pong and bikes.
Dining
Exceptional
(191 reviews)

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

Sheffield

8% off
AU$3,061
for 7 nights, 1 home
AU$437 per night
includes taxes & fees
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
Living area
Private kitchen
Living area
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Sheffield

8% off
AU$9,260
for 7 nights, 1 home
AU$1,323 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Kitchen
Kitchen
Dining room
Backyard looking east
Exceptional
(51 reviews)

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington

8% off
AU$4,948
for 7 nights, 1 home
AU$707 per night
includes taxes & fees
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Property grounds
Living Room
Front Gardens
Back Porch
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

Stockbridge

8% off
AU$4,372
for 7 nights, 1 home
AU$625 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Property grounds
Property grounds
We highly recommend the Sauna
After a day in the snow
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
AU$3,503
for 7 nights, 1 home
AU$500 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Private kitchen
Living area
Terrace/patio
Living area
Exceptional
(8 reviews)

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

Chatham

7% off
AU$4,110
for 7 nights, 1 home
AU$587 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
Great room river view
River view from window
Alfresco dining
dining area
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
AU$3,536
for 7 nights, 1 home
AU$505 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Front Porch
Living Room - Queen Sleep Sofa (First Floor)
Kitchen with Dining Area - well-equipped and great layout
Dining Room - table expands to seat 10
Exceptional
(10 reviews)

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

9% off
AU$4,113
for 7 nights, 1 home
AU$588 per night
includes taxes & fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lobby
Living area
Living area
Interior
Exceptional
(7 reviews)

The Race Mountain House

Sheffield

35% off
AU$5,395
for 7 nights, 1 home
AU$771 per night
includes taxes & fees
The Race Mountain House
Private kitchen
Room
Private kitchen
Outdoor dining
Exceptional
(32 reviews)

The Hideaway: Berkshire Home - Village of Egremont

egremont

16% off
AU$3,331
for 7 nights, 1 home
AU$476 per night
includes taxes & fees
The Hideaway: Berkshire Home - Village of Egremont
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
After a hard day on the trails or a long day on the town, relax in this oasis
Enjoy a beautiful crisp night under the lights
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$5,666
for 7 nights, 1 home
AU$809 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Living room with fireplace and forest views
Open kitchen area with bar seating, great for socializing while you meal prep.
Second story deck with lake views, dining table for 8, sitting area and grill
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$5,554
for 7 nights, 1 home
AU$793 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Exterior
Terrace/patio
Interior
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
AU$3,431
for 7 nights, 1 cottage
AU$490 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Interior
Interior
Kitchen
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,412
for 7 nights, 1 home
AU$773 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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