Pet Friendly Vacation Rentals
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    Pet Friendly Vacation Rentals in Chestertown, MD

    There are 11 pet friendly vacation rentals in Chestertown. 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 Allowed
    2+ Pets Allowed

    Pet-Friendly Airbnb Rentals

    Chestertown, MD
    $596
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 10

    River Lodge

    5.0 Chestertown, MD
    River Lodge Pet Policy This 4-room lodge in Chestertown is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. Visit Website
    $43
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    VRBO Chestertown

    Chestertown, MD
    VRBO Chestertown 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 Chestertown, 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 Chestertown to collect the pet fee. Visit Website
    $171
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Chestertown Airbnb Rentals

    Chestertown, MD
    Chestertown 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 Chestertown, please contact the host directly or read the House Rules section at the bottom of their listing. Visit Website
    $329
    No Pet Fee
    Small Dogs Only
    2+ Pets Allowed
    Sleeps 6

    Mallard House

    Chestertown, MD
    Mallard House Pet Policy This 2-bedroom vacation rental in Chestertown allows 2 dogs under 50 lbs for no additional fee. Cats and larger dogs may also be allowed by request, but all pets must be approved in advance. Pets are not allowed on the furniture. No wet dogs inside. Please bring your own dog towels. The property is not fenced and our dogs and the neighbors' dogs may come over. Visit Website
    $365
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 8

    Cliff Point Retreat

    5.0 Chestertown, MD
    Cliff Point Retreat Pet Policy This 3-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. Visit Website
    $850
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 15

    Historic Stepne Manor on the Eastern Shore

    5.0 Chestertown, MD
    Historic Stepne Manor on the Eastern Shore Pet Policy This 5-bedroom house in Chestertown allows dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. Visit Website
    $1,100
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 13

    Thornton Estate

    5.0 Chestertown, MD
    Thornton Estate Pet Policy This 6-bedroom house in Chestertown allows 2 dogs of any size for an additional fee of $100 per pet, per stay. Sorry, no cats. Pets must be approved in advance. Visit Website
    $234
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 10

    Country Estate in Historic District

    Chestertown, MD
    Country Estate in Historic District Pet Policy This 5-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request. Visit Website
    $284
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed

    Pet-Friendly Home on Chester River With Dock

    Chestertown, MD
    Pet-Friendly Home on Chester River With Dock Pet Policy This cottage in Chestertown allows pets of any size for an additional fee. Both dogs and cats are welcome. Visit Website
    $120
    + Pet Fee
    Small Dogs Only
    2+ Pets Allowed
    Sleeps 2

    Carriage House Hideaway in Middle of Chestertown

    Chestertown, MD
    Carriage House Hideaway in Middle of Chestertown Pet Policy This vacation rental in Chestertown allows 2 dogs under 50 lbs for an additional fee of $20 per pet, per stay. Sorry, no cats. Visit Website
    $449
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 10

    Private Waterfront Paradise With Pier

    Chestertown, MD
    Private Waterfront Paradise With Pier Pet Policy This 3-bedroom vacation rental in Chestertown allows 2 dogs of any size for an additional fee of $50 per pet, per stay. Sorry, no cats. Dogs are not permitted on the beds or furniture. Visit Website
    $285
    No Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 6

    Elbourns by the Bay

    5.0 Rock Hall, MD
    Elbourns by the Bay Pet Policy This 2-bedroom house in Rock Hall allows 2 dogs of any size for no additional fee. Sorry, no cats. Pets are not allowed on the furniture. Visit Website
    $457
    No Pet Fee
    Big Dogs Allowed
    1 Pet Max
    Sleeps 8

    Chesapeake Colonial Era Home

    Stevensville, MD
    Chesapeake Colonial Era Home Pet Policy This 4-bedroom vacation rental in Stevensville allows 1 dog of any size for no additional fee. Cats are also welcome, but pets are not permitted on the furniture. Due to the presence of farm animals, dogs must be leashed on the property. Visit Website
    $304
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 11

    Eastern Shore Beach House

    4.8 Betterton, MD
    Eastern Shore Beach House Pet Policy This 6-bedroom vacation rental in Betterton allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request. Visit Website
    $350
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 26

    Love Point Idyll

    Stevensville, MD
    Love Point Idyll Pet Policy This 5-bedroom vacation rental in Stevensville allows dogs of any size for an additional fee of $20 per pet, per night. Cats may also be allowed by request, but all pets must be approved in advance. Visit Website
    $765
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 10

    Chesapeake Bay Home with Pool

    5.0 Stevensville, MD
    Chesapeake Bay Home with Pool Pet Policy This 3-bedroom vacation rental in Stevensville allows 2 dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. Visit Website
    $900
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 12

    Historic 12 Acre Waterfront Home with Private Inn

    5.0 Centreville, MD
    Historic 12 Acre Waterfront Home with Private Inn Pet Policy This 6-bedroom villa in Centreville allows 3 dogs of any size for an additional fee of $50 per pet, per night. Cats may also be allowed by request. Visit Website
    $464
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 10

    Creek Cottage

    5.0 Centreville, MD
    Creek Cottage Pet Policy This 4-bedroom vacation rental in Centreville allows 2 dogs under 60 lbs for an additional fee of $150 per pet, per stay. Breed restrictions may apply. Sorry, no cats. Visit Website
    $174
    + Pet Fee
    Big Dogs Allowed
    2+ Pets Allowed
    Sleeps 6

    Moot Point Farm

    Greensboro, MD
    Moot Point Farm Pet Policy This 2-bedroom vacation rental in Greensboro allows dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request. Visit Website
    Chestertown, MD, US