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? 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.
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Pet Friendly The Lodge at Loon Lake
$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.
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$99+
No pet fee
Big dogs OK
2+ pets OK

Pet-Friendly Airbnb Rentals

Chestertown, NY
Pet Friendly A Beautiful Lake View Cabin on Friends Lake
$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.
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Pet Friendly Hillside Cottage at Birchwood
$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.
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Pet Friendly Lodge at Birchwood Cottages
$364
+$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.
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Pet Friendly Beautiful Lakeview Cottage on Friends Lake
$157
+$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.
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Pet Friendly Loon Lake
$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.
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Pet Friendly 7 Adirondack at Birchwood
$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.
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Pet Friendly Home Overlooking a Horse Farm
$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.
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Pet Friendly Loon Lookout Cottage at Birchwood
$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.
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Pet Friendly Lakeview #6
$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.
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Pet Friendly Modern Cabin with Hot Tub
$276
+$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.
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Pet Friendly Spectacular Lakefront Cabin on 12 Acres
$925
+$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.
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Pet Friendly Adirondacks Home with Fire Pit
$165
+$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.
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Pet Friendly All-Season Family Retreat W/ Dock on Loon Lake
$456
+ Pet fee
Big dogs OK
2+ pets OK

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.
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Pet Friendly Chester at Birchwood #3
$126
+$40 per pet
Big dogs OK
2+ pets OK
Sleeps 5

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.
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Pet Friendly Fireside at Birchwood #5
$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.
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Pet Friendly ADK Log Cabin Tucked in the Woods
$342
+$100 per pet
Big dogs OK
2 pets max
Sleeps 10

ADK Log Cabin Tucked in the Woods

4.8 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.
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Pet Friendly Elizabeth's Guest House
$387
+ Pet fee
Big dogs OK
2 pets max
Sleeps 18

Elizabeth's Guest House

4.1 Chestertown, NY
Elizabeth's Guest House Pet Policy
This 6-bedroom house in Chestertown allows 2 dogs of any size for an additional fee. Sorry, no cats.
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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!