Photo by Julie Miller

Find Pet-friendly Hotels in Chestertown, NY

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Check availability on Chestertown Pet-friendly Hotels

Tonight
31 May - 1 Jun
Tomorrow
1 Jun - 2 Jun
Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun

Compare Chestertown Pet-friendly Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"I would definitely stay here again."
The price is AED 643
AED 713 total
includes taxes & fees
12 Jun - 13 Jun
Pine Tree Motel & Cabins
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Smart TV, fireplace, foosball, books

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

10.0 out of 10, Exceptional, (31)
"We thoroughly enjoyed our stay and had a relaxing week."
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, (61)
"Second time staying here and continues to meet all expectations. Owner and on site managers all friendly and responsive. "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C
Terrace/patio

2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C

9.0 out of 10, Wonderful, (15)
"Stayed here for the weekend with my kids and friends and it was great! Will be back!"
2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C
#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, (11)
"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!
Dog-friendly cabin with lakefront location, 20' dock, smart TV
Fridge, microwave, oven, stovetop

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
Elizabeth. A Guest House Near Lake George.
Lake

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very Good, (40)
"There were 15 of us staying. This house was able to accommodate all of us and the young ones loved the pool! There was plenty of seating for meals. We enjoyed ourselves"
Elizabeth. A Guest House Near Lake George.
Log Cabin in the ADK’s on 30 acres
TV, fireplace

Log Cabin in the ADK’s on 30 acres

9.6 out of 10, Exceptional, (39)
"Beautiful cabin. Very peaceful and quiet "
Log Cabin in the ADK’s on 30 acres
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

8.8 out of 10, Excellent, (6)
"We had a great family time. Fire place and hot tub were a blast. We were lucky to have snow on Gore mountain and enjoyed skiing. Lovely property in the woods!"
Great Adirondacks retreat with five bedroomsHot tub,pool table.large open space
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

#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!
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.