Are you craving the green landscapes in Massachusetts? Vacation rentals in Great Barrington range from romantic cottages with beautiful views, to lakefront cabins, and even rustic log homes.

Top 15 Recommended vacation rentals in Great Barrington
Find your perfect vacation rental in Great Barrington from just $134 per night!
Vacation rentals and apartments with air conditioning
Vacation rentals with a balcony
Vacation Rentals With Fireplaces
Best Vacation Home Deals in Great Barrington
Save up to 22%
Choose a rental that fits your criteria among the 279 great rentals from 9 providers in Great Barrington. Using HomeToGo you can easily search and compare the offers of each available rental to find the best price and save up to 10%.
Budget-friendly Vacation Rentals in Great Barrington
Find Fantastic yet Inexpensive Offers
Top-Rated Rentals and Accommodations in Great Barrington
Book Vacation Rental Offers with the Highest User Rating
Why choose HomeToGo?

Securely pay and stay your way
Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service
Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews
Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises
Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple
Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay
Explore 15 million+ rentals, the world’s biggest selection of vacation homes.
Popular Rental Amenities in Great Barrington
One-third of the accommodations offer a pool, which makes Great Barrington a great place for travelers looking to make a splash. Additionally, more House rental have pools than any other property type. They are an excellent choice if you go in a group of 9, as that is the number of people they can welcome on average. more than half of Great Barrington's properties with pools are within two miles of water, choose between some pool time or waterfront moments.
Entertaining the kids: family fun in Great Barrington
If you are a family of skiiers, look no further than Ski Butternut, one of the most famous ski resorts in Great Barrington, located on Warner Mountain in the Berkshires. Offering stunning views of the alpine landscape, ski lessons, 2 terrain parks, and 22 trails, this is the best destination for winter family fun. Children who love hiking will enjoy Monument Mountain, which offers easy hikes through gorgeous terrain (particularly when the fall leaves are changing color). At Beartown State Forest, a scenic park with a fishing pond, you can see wildlife, enjoy winter sports, or take advantage of year-round hiking trails whenever you decide to visit.
Information about vacation rentals in Great Barrington
🏡 Vacation rentals available | 279 rentals |
---|---|
🌙 Nightly prices starting at | $134 |
⭐ Popular amenities | Pets allowed, Internet and Pool |
🐾 Pet friendly homes | 80 homes |
🏊 Vacation rentals with pools | 85 homes |
Frequently Asked Questions
What is the typical price per night for a vacation rental in Great Barrington?
The average accommodation in Great Barrington is priced at $134 per night. Nightly prices for house rentals are $704 on average. Bed and breakfast rentals in Great Barrington cost on average $318 per night.
How many vacation rentals are available to book in Great Barrington?
Currently there are 279 rentals to choose from for your next trip.
What are the most popular amenities for vacation homes in Great Barrington?
If you're looking to book a vacation rental in Great Barrington, others search for accommodation with these amenities: Internet, Pets allowed and Pool.
How many vacation rentals with a pool are in Great Barrington?
Great Barrington offers 85 Hotel room and Motel on offer to rent.
Are dogs allowed in vacation rentals in Great Barrington?
If you are traveling with a pet in Great Barrington - 29% of vacation homes are pet-friendly.
What's the best time to travel to Great Barrington?
When choosing a vacation rental in Great Barrington, consider that rainy season is typically in December or February, with August often being the driest.
Most Popular Destinations
- Cabin rentals in Gatlinburg, TN
- Vacation rentals in Yellowstone
- Vacation rentals in the Outer Banks
- Cabin rentals in Hocking Hills, OH
- Vacation rentals & cabins in Pigeon Forge
- Vacation rentals in Myrtle Beach
- Vacation Rentals in Vancouver, WA
- Vacation rentals in Vancouver
- Vacation rentals & cabins near Lake Tahoe
- Cabin rentals in Broken Bow, OK
- Vacation rentals & cabins in Yosemite
- Vacation rentals in Orlando
- Vacation rentals & cabins in Glacier National Park
- Vacation rentals in Gulf Shores
- Vacation rentals in San Diego
- Vacation rentals in Las Vegas
- Vacation rentals in Destin
- Vacation rentals & cabins in Branson
- Vacation rentals in Nashville
- Vacation rentals & cabins in Estes Park
- Vacation rentals in Key West
- Vacation rentals in Virginia Beach
- Vacation rentals in New Orleans
- Vacation rentals in Miami
- Cabin rentals in the Smoky Mountains, NC
- Vacation rentals in Panama City Beach
- Vacation rentals & cabins in Zion National Park
- Vacation rentals in Tybee Island
- Vacation rentals in Door County
- Vacation rentals in New York City
- Vacation rentals & cabins in the Great Smoky Mountains
- Vacation rentals in Chicago
- Vacation rentals & cabins in Big Bear Lake
- Vacation rentals & cabins in Sedona
- Vacation rentals on Block Island
- Vacation rentals in Maui
- Vacation rentals in Kauai
- Vacation rentals in Colorado Springs
- Vacation rentals in Nashville
- Vacation rentals & cabins in Colorado
- Vacation rentals in Siesta Key
- Vacation rentals in Charleston
- Vacation rentals in Palm Springs
- Vacation rentals in Orange Beach
- Vacation rentals in Anna Maria Island
- Vacation rentals in Paris
- Vacation rentals in Florida
- Vacation rentals in Cape May
- Vacation rentals in Atlanta
- Vacation rentals in Breckenridge
Top cities to visit
- Carmel
- Wilmington
- Cooperstown
- Catskill
- Saratoga Springs
- Springfield
- Stratton Mountain
- Albany
- Dover
- Lenox
- Rhinebeck
- New Haven
- Norwalk
- White Plains
- Manchester
- Stamford
- Oneonta
- Danbury
- Old Saybrook
- Greenwich
- White Lake
- Saugerties
- Bridgeport
- Yonkers
- Hunter
- Waterbury
- Amherst
- Windham
- Hartford, CT
- Beacon
- Milford
- New London
- Kingston
- Williamstown
- Northampton
- Port Jefferson
- Ludlow
- Stockbridge
- Diamond Point
- Old Lyme
- Westbrook
- Ashburnham
- Gloversville
- Ellenville
- Fleischmanns
- Washingtonville
- Hudson
- Woodstock
- Madison