Pet Friendly Vacation Rentals
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    Pet Friendly Vacation Rentals in Winchester, CT

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    There are 2 pet friendly vacation rentals in Winchester, and 212 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. All pet policy information is guaranteed and there are no booking fees!

    Pet Friendly Waterfront Summer Cottage
    $178
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 6

    Waterfront Summer Cottage

    4.9 Otis, MA
    Waterfront Summer Cottage Pet Policy This 2-bedroom cottage in Otis allows dogs of any size for no additional fee. Cats may also be allowed by request. Breed restrictions apply, and all pets must be approved in advance. Visit Website
    $6,645
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 2

    Charming Cabin on Scenic Road

    5.0 Great Barrington, MA
    Charming Cabin on Scenic Road Pet Policy This 1-bedroom cabin in Great Barrington is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $499
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 10

    Warm Welcome Great Barrington & the Berkshires

    5.0 Great Barrington, MA
    Warm Welcome Great Barrington & the Berkshires Pet Policy This 4-bedroom vacation rental in Great Barrington is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $500
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 18

    Summer Lake Cottage with Private Beach

    4.7 Lakeville, CT
    Summer Lake Cottage with Private Beach Pet Policy This 5-bedroom cottage in Lakeville is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $1,253
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 15

    Senff Estate

    5.0 Washington, CT
    Senff Estate Pet Policy This 8-bedroom house in Washington is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $275
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 8

    Great Barrington Getaway

    4.7 Great Barrington, MA
    Great Barrington Getaway Pet Policy This 3-bedroom house in Great Barrington allows 3 dogs of any size for no additional fee. Cats are also welcome. Visit Website
    $299
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 6

    Spectacular Fall Foliage in Sheffield

    5.0 Sheffield, MA
    Spectacular Fall Foliage in Sheffield Pet Policy This 3-bedroom house in Sheffield is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $400
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 7

    Lakeview Cottage with Dock & Kayaks

    4.8 Morris, CT
    Lakeview Cottage with Dock & Kayaks Pet Policy This 3-bedroom hotel room in Morris is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $1,450
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 10

    Old Litchfield 4BR Home & Pool

    5.0 Washington, CT
    Old Litchfield 4BR Home & Pool Pet Policy This 4-bedroom house in Washington allows 3 dogs of any size for no additional fee. Cats may also be allowed by request. Visit Website
    $193
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    New Hartford Airbnb Rentals

    New Hartford, CT
    New Hartford Airbnb Rentals Pet Policy 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 New Hartford, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $197
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Thomaston Airbnb Rentals

    Thomaston, CT
    Thomaston Airbnb Rentals Pet Policy 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 Thomaston, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $191
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Plymouth Airbnb Rentals

    Plymouth, CT
    Plymouth Airbnb Rentals Pet Policy 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 Plymouth, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $173
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Bristol Airbnb Rentals

    Bristol, CT
    Bristol Airbnb Rentals Pet Policy 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 Bristol, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $115
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Winsted Airbnb Rentals

    Winsted, CT
    Winsted Airbnb Rentals Pet Policy 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 Winsted, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $276
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Washington Depot Airbnb Rentals

    Washington Depot, CT
    Washington Depot Airbnb Rentals Pet Policy 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 Washington Depot, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $231
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Litchfield Airbnb Rentals

    Litchfield, CT
    Litchfield Airbnb Rentals Pet Policy 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 Litchfield, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $236
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Norfolk Airbnb Rentals

    Norfolk, CT
    Norfolk Airbnb Rentals Pet Policy 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 Norfolk, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $23
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Riverton Airbnb Rentals

    Riverton, CT
    Riverton Airbnb Rentals Pet Policy 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 Riverton, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $284
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Lakeville Airbnb Rentals

    Lakeville, CT
    Lakeville Airbnb Rentals Pet Policy 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 Lakeville, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $250
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Kent Airbnb Rentals

    Kent, CT
    Kent Airbnb Rentals Pet Policy 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 Kent, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    Winchester, CT, US