Photo by Julie Miller

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
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 SAR 656
SAR 729 total
includes taxes & fees
10 Jul - 11 Jul
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)
"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
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
#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!
Elizabeth. A Guest House Near Lake George.
Lake

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very Good, (41)
"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
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 Friends Lake and Loon Lake. While you’re there, make sure you don’t miss Hudson River and Loon Lake Beach.