Pet Friendly Vacation Rentals in Chestertown, NY

Pet Friendly Home Overlooking Racing Horse Farm

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.

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.

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.

Beautiful Lakeview Cottage on Friends Lake

4.7 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.

Fireside at Birchwood #5

4.7 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.

Hillside Cottage at Birchwood

4.7 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.

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.

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.

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.

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.

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.

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.

Home Overlooking a Horse Farm

4.5 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.

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.

Adirondacks Home with Fire Pit

4.8 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.

ADK Log Cabin Tucked in the Woods

4.7 Chestertown, NY

ADK Log Cabin Tucked in the Woods Pet Policy

This 3-bedroom vacation rental in Chestertown allows 2 dogs of any size for an additional fee of $100 per pet, per stay. Sorry, no cats.

Hermanus-on-the-Hudson

4.9 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.

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.

Lodge at Birchwood Cottages

4.8 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.

Raccoon Retreat at Lakeside

4.6 Chestertown, NY

Raccoon Retreat at Lakeside Pet Policy

This 2-bedroom vacation rental in Chestertown allows 1 dog of any size for an additional fee of $100 per pet, per stay. All pets must be approved in advance. Sorry, no cats.

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