Pet-Friendly Vacation Rentals in The Berkshires

The Whole Pack is Welcome in The Berkshires.

Don’t leave your best friend behind. Explore a curated collection of 4 luxury estates in The Berkshires designed for you and your pet.

Explore The Berkshires Stays

Fenced-In Freedom

Secure outdoor spaces in our The Berkshires homes so your dog can play safely while you relax by the pool.

Truly Pet-First

We’ve reimagined luxury travel to include the entire family. Our The Berkshires homes prioritize pet safety without compromising on world-class design.

Seamless Stays

Professional, pet-specific cleaning protocols and premium amenities like bowls and bags provided in every The Berkshires stay.

Beyond Just “Pet-Allowed”—Truly Pet-First in The Berkshires

At AvantStay, we understand that pets are part of the family. Our The Berkshires collection is hand-selected based on specific ‘Barkitecture’ criteria — prioritizing safety, durability, and high-end design. Whether you are looking for a home near Monument Mountain Trail (Leash required) or a spacious layout for group living near The Mount, Edith Wharton's Home, we ensure that bringing your four-legged companion never means sacrificing luxury.

When you aren’t relaxing in your designer living room, take your dog for a stroll at Burbank Park Dog Park (Dedicated off-leash area), or grab a drink on the patio at Alta Restaurant & Wine Bar. Travel with confidence knowing our guest experience team is available 24/7 to provide local pet care recommendations for your stay in The Berkshires.

Browse Our The Berkshires Pet-Friendly Homes

Pet Friendly
Sunny Pond EstateAusterlitz
7 Bedrooms
4 Bathrooms
14 Guests
Pet Friendly
Half MoonGreat Barrington
4 Bedrooms
2 Bathrooms
10 Guests
Pet Friendly
CordeliaLee
5 Bedrooms
3 Bathrooms
12 Guests
Pet Friendly
WhitneySheffield
5 Bedrooms
2 Bathrooms
10 Guests
Explore all The Berkshires pet-friendly homes

Guest Review

Karen W.

"We had the best time at this beach house! It was super clean, beautifully decorated, and had everything we needed for a relaxing stay. The pool was absolutely perfect —we spent so much time floating and relaxing there after the beach. The fenced yard was a huge plus, especially since we were able to bring our pup along. It’s so nice to find a pet-friendly place that’s this well cared for! The house had all the little touches that made it feel like home, and we can’t wait to come back again."

Frequently Asked Questions

Most of our The Berkshires homes welcome up to two well-behaved dogs. Specific house rules and local ordinances can be found on each listing page.

Absolutely! Beyond our private yards, we recommend checking out Berkshire Farmers Market, a favorite local tradition for pet owners in the area.

Yes, a specialized deep-cleaning fee is applied to all The Berkshires stays to ensure the home remains in pristine condition for every guest.

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