Photo by Julie Miller

Chestertown Hotel Guide - Pet Friendly Hotels in Chestertown, New York

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Check availability on Chestertown Pet Friendly Hotels

Tonight
19 Jul - 20 Jul
Tomorrow
20 Jul - 21 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Top Chestertown Pet Friendly Hotels

Pine Tree Motel & Cabins
Exterior

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 €167
includes taxes & fees
20 Jul - 21 Jul
Pine Tree Motel & Cabins
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Sun-loungers

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
Fridge, microwave, oven, stovetop

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

#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!
Elizabeth. A Guest House Near Lake George.
Lake

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
Interior

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
Property grounds

A beautiful lake view cabin on Friends Lake

9.6 out of 10, Exceptional, (50)
"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!
Exterior

#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
Smart TV

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

8.6 out of 10, Excellent, (7)
"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
#3 Chester @ Birchwood Cottages at Loon Lake. Family Friendly Waterfront
Fridge, microwave, oven, stovetop

#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 dog-friendly accommodation option in Chestertown?
Pine Tree Motel & Cabins is a top dog-friendly option for your stay. Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is another good option if you're bringing your pet along.
How many hotels that accept pets will I find in Chestertown?
Enjoy travelling with your furry pal at one of Expedia's 5 Chestertown accommodation options that accept pets.
What's the best time of year to travel to Chestertown with my pet?
When you're travelling with pets, keeping track of the weather can make the trip safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm 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.