Pet Friendly Hotels
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    Pet Friendly Hotels in Chestertown, NY

    There are 29 pet friendly hotels 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!

    Pet Friendly Home Overlooking Racing Horse Farm
    $123
    No pet fee
    Big dogs OK
    1 pet max
    Sleeps 10

    Home Overlooking Racing Horse Farm

    4.5 Chestertown, NY
    Home Overlooking Racing Horse Farm Pet Policy This 5-bedroom vacation rental in Chestertown allows dogs of any size for no additional fee! Just be sure to note that you're bringing a pet along on the booking form. Sorry, no cats. See Details
    $118
    No pet fee
    Big dogs OK
    2+ pets OK

    VRBO Chestertown

    Chestertown, NY
    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. See Details
    $99+
    No pet fee
    Big dogs OK
    2+ pets OK

    Pet-Friendly Airbnb Rentals

    Chestertown, NY
    $248
    No pet fee
    Big dogs OK
    2+ pets OK

    Chestertown Airbnb Rentals

    Chestertown, NY
    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. See Details
    $209
    +$50/pet/night
    Big dogs OK
    2+ pets OK

    The Lodge at Loon Lake

    Chestertown, NY
    The Lodge at Loon Lake Pet Policy The Lodge at Loon Lake allows dogs of any size for an additional fee of $50 per pet, per night. Sorry, no cats. See Details
    $195
    +$100 per pet
    Big dogs OK
    2 pets max
    Sleeps 4

    A Beautiful Lake View Cabin on Friends Lake

    4.8 Chestertown, NY
    A Beautiful Lake View Cabin on Friends Lake Pet Policy This 2-bedroom vacation rental in Chestertown allows 2 dogs of any size for an additional fee of $100 per pet, per stay. Cats are also welcome. See Details
    $140
    +$40 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 4

    Hillside Cottage at Birchwood

    4.8 Chestertown, NY
    Hillside Cottage at Birchwood Pet Policy This 3-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $40 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. See Details
    $405
    +$60 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 14

    Lodge at Birchwood Cottages

    4.9 Chestertown, NY
    Lodge at Birchwood Cottages Pet Policy This 4-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $60 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. See Details
    $175
    +$100 per pet
    Big dogs OK
    2 pets max
    Sleeps 4

    Beautiful Lakeview Cottage on Friends Lake

    4.8 Chestertown, NY
    Beautiful Lakeview Cottage on Friends Lake Pet Policy This 2-bedroom vacation rental in Chestertown allows 2 dogs of any size for an additional fee of $100 per pet, per stay. Cats are also welcome. See Details
    $390
    +$200 per pet
    Big dogs OK
    2 pets max
    Sleeps 10

    Loon Lake

    4.9 Chestertown, NY
    Loon Lake Pet Policy This 5-bedroom vacation rental in Chestertown allows 2 dogs of any size for an additional fee of $200 per pet, per stay. Cats may also be allowed by request. See Details
    $114
    +$50 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 10

    Home Overlooking a Horse Farm

    4.8 Chestertown, NY
    Home Overlooking a Horse Farm Pet Policy This 5-bedroom house in Chestertown allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request. See Details
    $195
    +$40 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 6

    7 Adirondack at Birchwood

    5.0 Chestertown, NY
    7 Adirondack at Birchwood Pet Policy This 3-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $40 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. See Details
    $126
    +$40 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 5

    Loon Lookout Cottage at Birchwood

    4.7 Chestertown, NY
    Loon Lookout Cottage at Birchwood Pet Policy This 2-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $40 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. See Details
    $170
    +$40 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 6

    Lakeview #6

    4.8 Chestertown, NY
    Lakeview #6 Pet Policy This 4-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $40 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. See Details
    $368
    +$75 per pet
    Big dogs OK
    2 pets max
    Sleeps 8

    Modern Cabin with Hot Tub

    5.0 Chestertown, NY
    Modern Cabin with Hot Tub Pet Policy This 3-bedroom lodge in Chestertown allows 2 dogs of any size for an additional fee of $75 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. Pets are not allowed on the furniture and must be crated if left unattended. A kennel and tie-outs are available. See Details
    $950
    +$50/pet/night
    Big dogs OK
    2 pets max
    Sleeps 20

    Spectacular Lakefront Cabin on 12 Acres

    5.0 Chestertown, NY
    Spectacular Lakefront Cabin on 12 Acres Pet Policy This 4-bedroom cabin in Chestertown allows 2 dogs of any size for an additional fee of $50 per pet, per night. Cats may also be allowed by request. See Details
    $164
    +$64 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 8

    Adirondacks Home with Fire Pit

    4.9 Chestertown, NY
    Adirondacks Home with Fire Pit Pet Policy This 3-bedroom house in Chestertown for an additional fee of $64 per pet, per stay. Cats may also be allowed by request. There is a fenced yard. See Details
    $428
    + Pet fee
    Big dogs OK
    2+ pets OK

    All-Season Family Retreat W/ Dock on Loon Lake

    5.0 Chestertown, NY
    All-Season Family Retreat W/ Dock on Loon Lake Pet Policy This 3-bedroom cottage in Chestertown allows pets of any size for an additional fee. Both dogs and cats are welcome. See Details
    $137
    +$40 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 5

    Chester at Birchwood #3

    4.2 Chestertown, NY
    Chester at Birchwood #3 Pet Policy This 3-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $40 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. See Details
    $153
    +$40 per pet
    Big dogs OK
    2+ pets OK
    Sleeps 6

    Fireside at Birchwood #5

    4.3 Chestertown, NY
    Fireside at Birchwood #5 Pet Policy This 4-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $40 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance. See Details
    Chestertown, NY, US