Owner Direct Vacation
Rentals in Great Barrington
The Best Owner Direct Vacation Rentals in Great Barrington. Explore thousands of vacation home rentals, large cabins, and villas near Great Barrington
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Explore the Best Great Barrington Vacation Homes
Looking for the perfect place to stay in Great Barrington? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Great Barrington character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Great Barrington Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Great Barrington
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Popular Neighborhoods for Great Barrington Vacation Rentals
What are the best areas to stay in Great Barrington
Discover the top neighborhoods in Great Barrington and choose a place that suits your stay.
Friday Feb 20
Great Barrington, Massachusetts
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Great Barrington vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Great Barrington
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How to Reserve Your Great Barrington Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Great Barrington Vacation Rental FAQs
1. What are the top vacation rentals in Great Barrington?
There are a lot of options in Great Barrington. If you plan on staying in the Great Barrington area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Great Barrington:
- Waterfront Cottage 10 Min From Great Barrington
- Charming Cottage, New Marlborough Village Green in the Berkshires
- Romantic Berkshires Cottage - Stunning Views, Pool
- Premiere Berkshire Country Estate w/Private Pool & Tennis Court - 5 mins to GB!
- Stunning Renovated Victorian
- The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
- Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
- NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
- Twin Maple Farm: Charming Modern Farmhouse
- Beautiful Berkshire Farm House on 160+ Acres
2. How many vacation rentals have private pools in Great Barrington?
There are 19 vacation rentals with private pools near Great Barrington. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Great Barrington are best for families?
If you are looking for a family-friendly vacation home in Great Barrington, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Great Barrington:
4. How many vacation rentals are available in Great Barrington?
Currently, the total number of properties listed in 2026 is over 297 in the Great Barrington area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Great Barrington.