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Find Pet-friendly Hotels in Chestertown, NY

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Check availability on Chestertown Pet-friendly Hotels

Top Chestertown Pet-friendly Hotels

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (129)
"Excellent location and staff was very friendly."
The price is AED 643
AED 713 total
includes taxes & fees
20 Jul - 21 Jul
Pine Tree Motel & Cabins

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

10.0 out of 10, Exceptional, (34)
"My wife and I absolutely loved our stay at Jackson's Lodge! The cabin is very spacious and contains all the amenities you need. The hot tub was an amazing experience at the end of a long day. The Simpsons arcade machine was a personal favorite! Would definitely stay here again."
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (62)
"My family and i had a great time here! The place is Amazing and we would definitely stay again! "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very Good, (42)
"It is an older house with a lot of character. For our very large family. The pool was super clean and a hit with everyone. Very convenient to lake George, and having a grocery store a very short walk away was a huge bonus!"
Elizabeth. A Guest House Near Lake George.

Dog-friendly cabin with lakefront location, 20' dock, smart TV

7.6 out of 10, Good, (24)
"We very much enjoyed this simple Adirondack cabin, the fireplace by the lake and the stunning views. Our only concerns were that the water comes from the lake (we wish we had been advised) and that lake access from the dock is very difficult to maneuver."
Dog-friendly cabin with lakefront location, 20' dock, smart TV

A beautiful lake view cabin on Friends Lake

9.6 out of 10, Exceptional, (49)
"Another wonderful relaxing stay. So happy to have spent another week here. And same as last year every thing went smoothly and we had a great time exploring and visiting with family. Thank you Amanda for another great stay!"
A beautiful lake view cabin on Friends Lake

#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

9.6 out of 10, Exceptional, (12)
"Absolutely loved our stay at Birchwood and we’d love to come back for many years to come!"
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

Great Adirondacks retreat with five bedroomsHot tub,pool table.large open space

8.8 out of 10, Excellent, (6)
"We loved everything about our stay and the accommodations The Hot Tub was a big hit as well as the fireplace.The kitchen had what we needed.The Outside Grill gave us the perfect Burger we only missed the Towels and not sure if I missed that on the listing we had three towels We would recommend this place to everyone Will definitely Re"
Great Adirondacks retreat with five bedroomsHot tub,pool table.large open space

#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

9.6 out of 10, Exceptional, (16)
"The views were absolutely amazing! We will definitely be back."
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

#3 Chester @ Birchwood Cottages at Loon Lake. Family Friendly Waterfront

8.4 out of 10, Very Good, (6)
"Love the lake!!"
#3 Chester @ Birchwood Cottages at Loon Lake. Family Friendly Waterfront
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

What's the best pet-friendly hotel in Chestertown?
Pine Tree Motel & Cabins is a top pet-friendly option for your stay. Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is another good choice for a stay with your pet.
How many hotels that accept pets will I be able to find in Chestertown?
Frolic with your furry friend at one of Expedia's 5 Chestertown hotels that allow pets.
What's the best time of year to travel to Chestertown with my pet?
When you're traveling with pets, keeping track of the weather can help you make the trip more safe and fun for everyone. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What is there to see and do with your pet in Chestertown?
Known for its waterfront, Chestertown has lots to offer visitors. See the local sights and visit Loon Lake Beach and Friends Lake. While you're there, make sure you don't miss Loon Lake and Hudson River.