Pet Friendly Hotels in Chestertown, NY

There are 29 pet friendly hotels in Chestertown. 22 welcome two or more pets, and 28 have no weight limit. Need help to decide where to stay with your dog? 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!

Basic Adirondack Camp

3.8 Chestertown, NY

Basic Adirondack Camp Pet Policy

This 3-bedroom vacation rental in Chestertown allows 1 dog of any size for an additional fee of $20 per night. A second dog may be allowed by request. Sorry, no cats.

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.

Pet-Friendly Airbnb Rentals

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.

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.

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.

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.

All-Season Family Retreat W/ Dock on Loon Lake

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.

Chester at Birchwood #3

4.3 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.

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.

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.

Private Dock & Yard Lakefront Adirondacks Escape

Chestertown, NY

Private Dock & Yard Lakefront Adirondacks Escape Pet Policy

This 2-bedroom cottage in Chestertown allows dogs of any size for an additional fee of $136 per stay. Cats may also be allowed by request.

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.

Drake's Motel and Restaurant

Schroon Lake, NY

Drake's Motel and Restaurant Pet Policy

Drake's Motel and Restaurant allows pets of any size for an additional fee of $15 per pet, per night. Both dogs and cats are welcome.

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.

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.

Rustic Adirondacks Home with Hot Tub & Lake Access

Chestertown, NY

Rustic Adirondacks Home with Hot Tub & Lake Access Pet Policy

This 3-bedroom cottage in Chestertown allows pets of any size for an additional fee of $89 per stay. Both dogs and cats are welcome.

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.

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.

Hermanus-on-the-Hudson

5.0 Chestertown, NY

Hermanus-on-the-Hudson Pet Policy

This 3-bedroom apartment in Chestertown allows 1 dog under 20 lbs for an additional fee of $15 per night. Sorry, no cats. Please clean up after your pets.

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There are 29 pet friendly hotels in Chestertown, NY. 22 welcome two or more pets, and 28 have no weight limit. Do you know of a pet friendly hotel we've missed? to BringFido!