How many pet-friendly vacation rentals are available in Cheshire on 7oceanvacation?

There are more than 19 pet-friendly rentals available on 7oceanvacation. Check prices and availability in Cheshire 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 Cheshire?

There are many dog-friendly vacation homes available in Cheshire. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Cheshire: Ski at 19th c. Barn in the Berkshires Mountain getaway in the Berkshires - walk to trails & town! 2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox The Springs Motel

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

Most definitely! There are many luxury places to stay in Cheshire. 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 Cheshire. Though note, more expensive is not always better.

What is the price of a pet-friendly rental in Cheshire, Massachusetts?

The average price of a pet-friendly vacation home is $453 . Find our pet-friendly accommodation near Cheshire.

What are the most family-friendly holiday rentals near Cheshire?

At 7oceanvacation, many of our accommodations are perfect for families and allow dogs too. Check out the complete list of pet-friendly holiday rentals in Cheshire to find what works for you.

Pet Friendly Vacation Rentals in Cheshire

From US $372

9.6 (93 Reviews)

House

Ski at 19th c. Barn in the Berkshires

Air Conditioner
Parking
Pet Friendly

Cheshire Pet Friendly Vacation Rentals & Homes

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