Pet Friendly Vacation Rentals in Windsor, MA

Pet policies are determined by the individual host of each Airbnb property. For more information on the pet fee, weight limit, and other restrictions at a particular property in Windsor, please contact the host directly or read the House Rules section at the bottom of their listing.

Pet policies are determined by the individual owner of each Vrbo property. For more information on the pet fee, weight limit and other restrictions at a dog-friendly Vrbo in Windsor, please contact the owner directly or read the 'House Rules' section of their listing. Also be sure to include your pet(s) in the 'Guest' field when making your reservation, so the pet fee can be included. If applicable, it will be usually be displayed in the 'On-site Fees' or 'Owner Fees' sections during checkout. Some owners will also wait until you arrive in Windsor to collect the pet fee.

Dogs of any size are allowed at this 3-bedroom vacation rental in Williamstown for an additional fee of $50 per pet, per stay. Cats may also be allowed by request.

This 13-bedroom cottage in Stephentown allows 2 dogs of any size for an additional fee of $152 per stay. Cats may also be allowed by request.

This 3-bedroom vacation rental in West Stockbridge allows dogs of any size for a fee of $50 per pet, per stay. Cats may also be allowed by request.

This 4-bedroom apartment in Hancock allows dogs of any size for an additional fee of $137 per stay. Cats may also be allowed by request.

This 5-bedroom cottage in Pittsfield allows 2 pets of any size for an additional fee of $137 per stay. Both dogs and cats are welcome.

This 2-bedroom vacation rental in Lee allows dogs of any size for an additional fee of $25 per pet, per stay. Cats may also be allowed by request.

This 3-bedroom house in Pownal allows 1 dog of any size for an additional fee of $15 per night. Cats are also welcome. Pets must be kept on a leash outdoors due to the presence of a neighboring dog.

This 4-bedroom cottage in Great Barrington allows dogs of any size for an additional fee of $130 per stay. Sorry, no cats.

This 3-bedroom vacation rental in Pittsfield allows 1 dog up to 50 lbs for an additional fee of $50 per stay. Cats are also welcome.

This 3-bedroom vacation rental in Hawley allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request. Pets must be crated if left unattended.

This 3-bedroom vacation rental in Pittsfield allows dogs of any size for an additional fee of $30 per pet, per night. Cats may also be allowed by request.

This 4-bedroom vacation rental in Whitingham allows 2 dogs under 50 lbs for an additional fee of $35 per pet, per stay. Cats are also welcome.

This 3-bedroom house in Plainfield allows dogs of any size for an additional fee. Cats may also be allowed by request, but all pets must be approved in advance.

This 3-bedroom vacation rental in Peru allows dogs of any size for an additional fee of $15 per pet, per stay. All pets must be approved in advance. Sorry, no cats.

This 4-bedroom vacation rental in North Adams allows 2 dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request.

This 4-bedroom house in Lenox is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request.

This 5-bedroom vacation rental in Williamstown allows 2 dogs of any size for an additional fee of $50 per pet, per stay. Cats are also welcome. Pets must be housebroken and are not allowed in the carpeted bedrooms.