We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Holiday Rentals
Restaurants
Things to do
Skip to main content
Review
Trips
Alerts
Sign in
Inbox
See all
Sign in
to get trip updates and message other travellers.
Great Barrington
Great Barrington Tourism
Great Barrington Accommodation
Great Barrington Bed and Breakfast
Great Barrington Holiday Rentals
Great Barrington Holiday Packages
Great Barrington Flights
Great Barrington Restaurants
Great Barrington Attractions
Great Barrington Travel Forum
Great Barrington Photos
Great Barrington Map
Great Barrington Guide
Hotels
All Great Barrington Hotels
Great Barrington Hotel Deals
Last Minute Hotels in Great Barrington
By Hotel Type
By Hotel Class
By Hotel Brand
Popular Amenities
Popular Great Barrington Categories
Near Airports
Near Colleges
Great Barrington Motels
Family Hotels Great Barrington
Business Hotels Great Barrington
Great Barrington Green Hotels
5-stars Hotels in Great Barrington
4-stars Hotels in Great Barrington
3-stars Hotels in Great Barrington
Wyndham Hotels in Great Barrington
Pet Friendly Hotels in Great Barrington
Great Barrington Hotels with a Pool
Cheap Hotels Great Barrington
Ski Hotels in Great Barrington
Clean Hotels in Great Barrington
Hotels with Complimentary Breakfast in Great Barrington
Hotels with Restaurants in Great Barrington
Great Barrington Pet Friendly Motels
Hotels near (BDL) Bradley Intl Airport
Hotels near (ALB) Albany Intl Airport
Hotels near Bard College at Simon's Rock
Things to do
Restaurants
Flights
Holiday Rentals
Places of Interest
Colleges & Universities
Holiday Rentals near Ski Butternut
Holiday Rentals near National Shrine of the Divine Mercy
Holiday Rentals near Monument Mountain
Holiday Rentals near Housatonic River Walk
Holiday Rentals near Bard College at Simon's Rock
Shopping
Package Holidays
Cruises
Rental Cars
Tours
Add a Place
Travel Forum
Airlines
Best of 2022
Help Centre
Travel Articles
Great Barrington, MA Holiday Rentals, Apartments and Villas
Holiday Rentals
USA
Massachusetts (MA)
Berkshires
Great Barrington Apartments
Search
Great Barrington Holiday Apartments
List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
View Map
Bedrooms
Any
Bathrooms
Any
Amenities
Internet (38)
Washer/Dryer (35)
Parking (33)
Air Conditioning (32)
Show more
Suitability
Kid friendly (34)
Elder access (4)
Pet friendly (2)
Smoking allowed (2)
Show more
Property type
Holiday Rental House (38)
Condominium/Apartment (3)
Cabin Holiday Rental (0)
Private Room (0)
Show more
Distinctive Features
Boat Available (6)
Housekeeping Included (4)
Mountain Views (3)
Waterfront (1)
Show more
Distance from
1 km
41 rentals
in Great Barrington.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order.
Learn more.
Berkshires: Romantic Cottage with spectacular view
24 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!
92 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Downtown GB apartment walk to shops and restaurants
57 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Location Location! Comfort and Privacy So Close to Downtown
54 reviews
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
2 bedroom Riverhouse in the Heart of the Berkshires
41 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Great Barrington apartment, Short walk to downtown
50 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Stunning Renovated Victorian
31 reviews
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Beautiful Berkshire Farm House on 160+ Acres
31 reviews
Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Minutes from downtown Great Barrington, Convenient location
32 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
COZY LOG HOME* fireplace, skiing,fall foliage Hiking, Berkshires*
59 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Save time - get the best
Great Barrington
rentals sent straight to your email!
Get the List
Lake Community - Near Town, Attractions
27 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
NEW SECLUDED 3 BEDROOM COUNTRY CASTLE
16 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 14
21 reviews
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Charming Housatonic Village Cape
21 reviews
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Monthly Discount for Ski Season Rental at Lakefront House in Great Barrington
16 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!
12 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington
13 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Romantic Berkshires Cottage - Stunning Views, Pool
11 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Deluxe Home w/ Pool on The Hill
11 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Barn Apartment in Gorgeous Stonybrook Farm
21 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!
9 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
NEW! Serene Great Barrington Cottage w/ Fire Pit!
10 reviews
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Modern Victorian on the Hill
8 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Idyllic Berkshire Get Away: Balance of relaxation and convenience
17 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
New to Market Renovated Home, 5 min walk to town
6 reviews
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Gem of the Berkshires, walk to downtown & lake.
4 reviews
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
Upscale Country Cottage
5 reviews
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Lakefront Berkshires Ski/Summer House, Great Views
4 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
A Four Seasons Woodland Lodge
3 reviews
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr
3 reviews
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
A great escape; secluded but close to all - contemporary home, mountain views
2 reviews
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
23 reviews
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Beautiful house on 'The Hill' just minutes from Lake Mansfield and Town.
1 review
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Classic Berkshire Cottage in Sun-Drenched Meadow
1 review
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Eco-friendly cozy home in Gt. Barrington
1 review
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
Renovated house on the Hill. Walk everywhere!
1 review
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Renovated family friendly house close to everything and endless views
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Luxurious modern estate w/ heated pool, hot tub, and lakefront!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Farmhouse from a magazine
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
NEW! Cozy Great Barrington Home 1 Mi to Ski Resort
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
Payment Protection
Previous
Next
1
Frequently Asked Questions about Great Barrington
Do any holiday rentals in Great Barrington have a pool?
Yes, here are some popular holiday rentals in Great Barrington that have a pool:\n
\n
Berkshires: Romantic Cottage with spectacular view
\n
Renovated family friendly house close to everything and endless views
\n
Romantic Berkshires Cottage - Stunning Views, Pool
\n
\n
See all holiday rentals with a pool in Great Barrington on Tripadvisor
Do any holiday rentals in Great Barrington have internet access?
Yes, here are some popular holiday rentals in Great Barrington that have internet access:\n
\n
Berkshires: Romantic Cottage with spectacular view
\n
Lakefront Berkshires Ski/Summer House, Great Views
\n
Gem of the Berkshires, walk to downtown & lake.
\n
\n
See all holiday rentals in Great Barrington on Tripadvisor
What are the best pet friendly rentals in Great Barrington?
The best pet friendly rentals in Great Barrington are:\n
\n
Lakefront Berkshires Ski/Summer House, Great Views
\n
Eco-friendly cozy home in Gt. Barrington
\n
Berkshires: Romantic Cottage with spectacular view
\n
\n
See all pet friendly holiday rentals in Great Barrington on Tripadvisor
What are some great rentals in Great Barrington that are kid friendly?
Some of the most popular kid friendly rentals in Great Barrington are:\n
\n
Lakefront Berkshires Ski/Summer House, Great Views
\n
Gem of the Berkshires, walk to downtown & lake.
\n
Eco-friendly cozy home in Gt. Barrington
\n
\n
See all kid friendly holiday rentals in Great Barrington on Tripadvisor