What are the top rated Cottage Rentals in The Berkshires?

There are a lot of options in The Berkshires. If you plan on staying in the The Berkshires area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in The Berkshires: <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/lakefront-cottage-in-the-berkshires-in-western-massachusetts/HA-3211250817" class="class="static-page-link"">Lakefront Cottage In The Berkshires In Western Massachusetts</a> <a href="/property/stay-at-beaver-lodge/HA-3213031033" class="class="static-page-link"">Stay at Beaver Lodge!</a> <a href="/property/ashintully-cottage-in-spectacular-setting/HA-1213023396" class="class="static-page-link"">Ashintully Cottage in spectacular setting</a> <a href="/property/endearing-cottage-in-the-berkshires-walking-distance-to-downtown-and-mass-moca/HA-3213396824" class="class="static-page-link"">Endearing cottage in the Berkshires, walking distance to downtown and Mass MoCA.</a> <a href="/property/designer-berkshire-cottage/HA-3212964171" class="class="static-page-link"">Designer Berkshire Cottage</a> <a href="/property/charming-lakeview-cottage-in-heart-of-the-berkshires/HA-3214434066" class="class="static-page-link"">Charming Lakeview Cottage in Heart of the Berkshires</a> <a href="/property/charming-1-bedroom-cottage-on-the-border-of-plainfield-savoy-on-windsor-pond/HA-3214750325" class="class="static-page-link"">Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!</a> <a href="/property/enchanted-cottage-on-babbling-brook/HA-1213960887" class="class="static-page-link"">Enchanted Cottage On Babbling Brook</a>

How much does it cost to rent a cottage in The Berkshires?

The average cost for a cottage rental in The Berkshires is $291 per night. Piratecovecottages has a wide list of great cottages near The Berkshires that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in The Berkshires that allow pets?

Yes, here are the top cottage rentals in The Berkshires that allow you to bring your pet: Charming historic cottage on scenic road to Mt. Greylock Rustic Berkshires Cottage at Lake Buel with Kayaks! Luxury Vacation Rental in the Berkshires! Waterfront Cottage 10 Min From Great Barrington <a href="/all/usa/massachusetts/the-berkshires" class="class="static-page-link"">See all pet-friendly vacation rentals in The Berkshires on Piratecovecottages</a>

Do you have any rental cottages in The Berkshires that are suitable for families?

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

Are there quality cottages in The Berkshires that have indoor swimming pools?

As of 2026, the data from Piratecovecottages shows that there are Over 82 private swimming pools or cottages with indoor pools in the The Berkshires area along with other great amenities.

The Berkshires Cottage Rentals By Owner

Charming historic cottage on scenic road to Mt. Greylock

From US $222

10.0 (118 Reviews)

Cottage

Charming historic cottage on scenic road to Mt. Greylock

Air Conditioner
Parking
TV

The Berkshires Cottage Rentals & Holiday Homes

Find the best cottages in The Berkshires - We found 82 exact matches

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