Pet Friendly Vacation Rentals
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    Pet Friendly Vacation Rentals in Windsor, MA

    There are 2 pet friendly vacation rentals in Windsor, and 193 more nearby. Need help to decide where to stay with your dog? You can browse the results below and filter by amenities to find the perfect spot. BringFido members never pay a booking fee, and their reservations are backed by our Pet Friendly Guarantee!

    $99+
    No pet fee
    Big dogs OK
    2+ pets OK

    Pet-Friendly Airbnb Rentals

    Windsor, MA
    $320
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 8

    Brooklyn Zoo

    5.0 North Adams, MA
    Brooklyn Zoo Pet Policy 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. Visit Website
    $359
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 4

    The 1843 Morewood Schoolhouse

    4.9 Pittsfield, MA
    The 1843 Morewood Schoolhouse Pet Policy 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. Visit Website
    $910
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 15

    Quarry Hill Farm

    4.9 Pownal, VT
    Quarry Hill Farm Pet Policy This 8-bedroom farmhouse in Pownal is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $552
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 8

    William Cook House

    4.9 Middlefield, MA
    William Cook House Pet Policy 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. Visit Website
    $2 199
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 30

    The Kemble

    5.0 Lenox, MA
    The Kemble Pet Policy This 13-bedroom villa in Lenox is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $194
    No pet fee
    Big dogs OK
    3 pets max
    Sleeps 7

    Central Haus (Group Getaway on a Quiet Street)

    5.0 North Adams, MA
    Central Haus (Group Getaway on a Quiet Street) Pet Policy This 3-bedroom house in North Adams allows 3 dogs of any size for no additional fee. Cats are also welcome. Visit Website
    $420
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 6

    Berkshire Waterfront Lakehouse

    4.8 Lanesborough, MA
    Berkshire Waterfront Lakehouse Pet Policy This 3-bedroom vacation rental in Lanesborough allows 2 dogs of any size for no additional fee. Pets are not allowed on the furniture. Cats may also be allowed by request. Visit Website
    $463
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 6

    Froggy Pond

    5.0 Stephentown, NY
    Froggy Pond Pet Policy 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. Visit Website
    $280
    No pet fee
    Big dogs OK
    3 pets max
    Sleeps 8

    Country Comfort

    4.8 Stephentown, NY
    Country Comfort Pet Policy 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. Visit Website
    $421
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 5

    Charming Home on Lake Mahkeenac

    4.9 West Stockbridge, MA
    Charming Home on Lake Mahkeenac Pet Policy 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. Visit Website
    $528
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 8

    Sophisticated Lenox Retreat Minutes to Downtown

    4.9 Lenox, MA
    Sophisticated Lenox Retreat Minutes to Downtown Pet Policy 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. Visit Website
    $571
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 14

    5-Bedroom House with Indoor and Outdoor Pools

    4.7 Lenox, MA
    5-Bedroom House with Indoor and Outdoor Pools Pet Policy This 5-bedroom vacation rental in Lenox is pet friendly! Pets of any size are welcome for no additional fee, however there is a cleaning fee of $150 per stay for all guests. Sorry, no cats. Visit Website
    $420
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 4

    The Barn

    5.0 Williamstown, MA
    The Barn Pet Policy This 1-bedroom barn in Williamstown allows 2 dogs of any size for no additional fee. Sorry, no cats. Visit Website
    $472
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 9

    Mason Hill

    4.8 Cheshire, MA
    Mason Hill Pet Policy This 3-bedroom barn in Cheshire allows 2 dogs of any size for no additional fee. Sorry, no cats. Visit Website
    $421
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 10

    Brooksong

    5.0 Dalton, MA
    Brooksong Pet Policy This 5-bedroom house in Dalton allows 2 dogs of any size for no additional fee. Sorry, no cats. Visit Website
    $378
    No pet fee
    Big dogs OK
    2 pets max
    Sleeps 4

    Charming 18th Century Farmhouse

    4.5 Williamstown, MA
    Charming 18th Century Farmhouse Pet Policy This 2-bedroom farm in Williamstown allows 2 dogs of any size for no additional fee. Sorry, no cats. Visit Website
    $208
    No pet fee
    Big dogs OK
    2+ pets OK
    Sleeps 6

    Healthcare Central Apartment

    4.3 Lanesborough, MA
    Healthcare Central Apartment Pet Policy This 2-bedroom apartment in Lanesborough is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $116
    No pet fee
    Big dogs OK
    2+ pets OK

    VRBO Windsor

    Windsor, MA
    VRBO Windsor Pet Policy 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. Visit Website
    $163
    No pet fee
    Small dogs only
    2+ pets OK
    Sleeps 4

    Walk to Downtown Williamstown

    4.7 Williamstown, MA
    Walk to Downtown Williamstown Pet Policy Small dogs are welcome in this 2-bedroom house in Williamstown for no additional fee. Cats may also be allowed by request. Visit Website
    Windsor, MA, US