Pet Friendly Holiday 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.

This 2-bedroom vacation rental in Becket allows 1 dog of any size for an additional fee of $20 per stay. Sorry, no cats.

This 2-bedroom vacation rental in Becket allows dogs of any size for an additional fee of $75 per pet, per stay. All pets must be approved in advance. No cats or puppies.

This 1-bedroom house in Pittsfield is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. There is a fenced yard.

This 2-bedroom farm in Williamstown allows 2 dogs of any size for no additional fee. Sorry, no cats.

This 3-bedroom house in North Adams allows 3 dogs of any size for no additional fee. Cats are also welcome.

This 1-bedroom cottage in Richmond allows 1 dog of any size for an additional fee of $35 per stay. Sorry, no cats. The yard is fenced.

This 4-bedroom house in Stephentown allows 3 dogs of any size for no additional fee. Please use sheets to cover the furniture. Cats may also be allowed by request, but only crated pets may be left unattended.

This 3-bedroom barn in Cheshire allows 2 dogs of any size for no additional fee. Sorry, no cats.

Dogs of any size are allowed at this 2-bedroom house in Becket for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

This 3-bedroom house in West Stockbridge is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request.

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

This 2-bedroom villa in South Lee allows dogs of any size for an additional fee of $140 per pet, per stay. Cats may also be allowed by request. Vaccination records are required.

This 3-bedroom house in Richmond allows 2 dogs under 50 lbs for an additional fee of $100 per pet, per stay. Sorry, no cats.

This 4-bedroom house in North Adams allows 2 dogs of any size for no additional fee. Cats may also be allowed by request, but all pets must be approved in advance.

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 1-bedroom barn in Williamstown allows 2 dogs of any size for no additional fee. Sorry, no cats.

This 3-bedroom house in Stephentown allows 2 dogs of any size for no additional fee. Cats may also be allowed by request, but all pets must be approved in advance.