What are the top rated Cottage 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 Cottage Rentals in Great Barrington: <a href="/property/charming-cottage-new-marlborough-village-green-in-the-berkshires/HA-121214201" class="class="static-page-link"">Charming Cottage, New Marlborough Village Green in the Berkshires</a> <a href="/property/romantic-berkshires-cottage-stunning-views-pool/HA-1214525359" class="class="static-page-link"">Romantic Berkshires Cottage - Stunning Views, Pool</a> <a href="/property/incredible-ski-lodge-7500-square-ft-log-cabin-moose-lodge/HA-3214267028" class="class="static-page-link"">Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge</a> <a href="/property/twin-maple-farm-charming-modern-farmhouse/HA-3114264301" class="class="static-page-link"">Twin Maple Farm: Charming Modern Farmhouse</a> <a href="/property/converted-berkshire-schoolhouse-on-a-quiet-river/HA-3211755320" class="class="static-page-link"">Converted Berkshire schoolhouse on a quiet river</a> <a href="/property/private-woodland-getaway-minutes-from-ski-butternut/HA-3211315048" class="class="static-page-link"">Private Woodland Getaway minutes from Ski Butternut</a> <a href="/property/log-style-home-4-miles-to-catamount-with-fitness-room/HA-1214277978" class="class="static-page-link"">Log style home 4 miles to Catamount with fitness room</a> <a href="/property/hang-by-the-pool-or-walk-to-town/HA-1217888741" class="class="static-page-link"">Hang By The Pool or Walk To Town</a> <a href="/property/little-gem-on-baldwin-hill-in-south-egremont/HA-321719709" class="class="static-page-link"">Little Gem On Baldwin Hill In South Egremont</a> <a href="/property/timberdoodle-a-mountainside-retreat/HA-1217849963" class="class="static-page-link"">Timberdoodle-a mountainside retreat</a>

How much does it cost to rent a cottage in Great Barrington?

The average cost for a cottage rental in Great Barrington is $587 per night. Monttremblantrentals has a wide list of great cottages near Great Barrington that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Great Barrington that allow pets?

Yes, here are the top cottage rentals in Great Barrington that allow you to bring your pet: Premiere Berkshire Country Estate w/Private Pool & Tennis Court - 5 mins to GB! Windflower Inn Charming 6 Bdrm Countryside Stay Massachusetts Lake House w/Dock - Pets Welcome! <a href="/all/usa/massachusetts/great-barrington" class="class="static-page-link"">See all pet-friendly vacation rentals in Great Barrington on Monttremblantrentals</a>

Do you have any rental cottages in Great Barrington that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Great Barrington to find one that works for you.

Are there quality cottages in Great Barrington that have indoor swimming pools?

As of 2026, the data from Monttremblantrentals shows that there are Over 275 private swimming pools or cottages with indoor pools in the Great Barrington area along with other great amenities.

Great Barrington Cottage Rentals By Owner

Premiere Berkshire Country Estate w/Private Pool & Tennis Court - 5 mins to GB!

From US $1,064

10.0 (55 Reviews)

House

Premiere Berkshire Country Estate w/Private Pool & Tennis Court - 5 mins to GB!

Air Conditioner
Parking
Pet Friendly

Great Barrington Cottage Rentals & Holiday Homes

Find the best cottages in Great Barrington - We found 275 exact matches

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