What are the top rated Pet Friendly Vacation 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 Pet Friendly Vacation Rentals in The Berkshires: <a href="/property/swiss-chalet-style-timber-frame-home-in-berkshires-with-all-modern-conveniences/HA-1213792910" class="class="static-page-link"">Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences</a> <a href="/property/elterwater-swan-lake-your-own-lakefront-oasis-a-true-berkshire-getaway/HA-321424508" class="class="static-page-link"">“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway</a> <a href="/property/huge-luxe-williamstown-updated-victorian-all-ensuite-baths-walk-to-spring-st/HA-321857164" class="class="static-page-link"">Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!</a> <a href="/property/cozy-monterey-family-chalet-minutes-from-lake-10-minutes-from-butternut/HA-321480749" class="class="static-page-link"">Cozy Monterey Family Chalet, Minutes From Lake &amp; 10 Minutes From Butternut!</a> <a href="/property/spectacular-88-acre-berkshires-retreat-w-tennis-court-family-friendly/HA-32195599" class="class="static-page-link"">Spectacular 88-acre Berkshires Retreat w/Tennis Court - Family Friendly</a> <a href="/property/custom-home-on-9-scenic-acres-near-small-lake-sleeps-up-to-16/HA-321582524" class="class="static-page-link"">Custom Home on 9 scenic acres near small lake, Sleeps up to 16.</a> <a href="/property/sprawling-berkshires-ranch-nestled-in-a-private-wooded-lot-with-expansive-yards/HA-321580967" class="class="static-page-link"">Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!</a> <a href="/property/spectacular-setting-on-your-own-private-lake-close-to-it-all/HA-3211077576" class="class="static-page-link"">Spectacular setting on your own private lake close to it all!</a> <a href="/property/family-friendly-in-sheffield-private-yet-close-to-everything/HA-3211846901" class="class="static-page-link"">Family Friendly in Sheffield, private yet close to everything!</a> <a href="/property/romantic-berkshires-cottage-stunning-views-pool/HA-1214525359" class="class="static-page-link"">Romantic Berkshires Cottage - Stunning Views, Pool</a>

How many pet-friendly vacation rentals are available in The Berkshires on Nighttravels?

There are more than 481 pet-friendly rentals available on Nighttravels. Check prices and availability in The Berkshires and last updated on January 2026. Check an individual property if they have restrictions on the size or numbers of pets.

Which is the best dog-friendly place to stay in The Berkshires?

There are many dog-friendly vacation homes available in The Berkshires. Here are the most popular pet-friendly places, ranked by their guest rating as listed in The Berkshires: Premiere Berkshire Country Estate w/Private Pool & Tennis Court - 5 mins to GB! Granville House Inn at Kenmore Hall Massachusetts Lake House w/Dock - Pets Welcome!

Do you have any luxury vacation homes that allow pets in or near The Berkshires?

Most definitely! There are many luxury places to stay in The Berkshires. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in The Berkshires. Though note, more expensive is not always better.