Photo by Julie Miller

Find Pet-friendly Hotels in Chestertown, NY

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Check availability on Chestertown Pet-friendly Hotels

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

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"
Pine Tree Motel & Cabins

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

10.0 out of 10, Exceptional, (28)
"My family and I (wife and 2 children ages 15 and 11) had an absolutely wonderful time staying at this vacation rental. It was quiet, clean, spacious and so relaxing. The property was large and beautiful and the house had ample space for all of us to spread out although most of our time was spent in the living room in front of the wood burning stove. The house had all the amenities anyone could ask for to make the stay inviting and comfortable. The beds were super comfortable and the hot tub was...
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, (58)
"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

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very Good, (39)
"The house has a lot of character. Great quiet neighborhood. Gas station, grocery store, pharmacy, and ice cream shop within walking distance. Dog park near by. Heated swimming pool was very nice and relaxing. Property manager made sure we were happy with our stay."
Elizabeth. A Guest House Near Lake George.

Rustic Adirondacks Home w/ Hot Tub & Lake Access!

9.8 out of 10, Exceptional, (19)
"I am so glad I pickednthat spot. Everything was just as described. It took us 10 min to get to Gore. We had beautiful views of the lake in the morning and are ski we used the hot tub. Awesome "
Rustic Adirondacks Home w/ Hot Tub & Lake Access!

Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!

9.8 out of 10, Exceptional, (51)
"We stayed for a winter holiday weekend and were charmed by the view of the frozen-over Loon Lake with its ice fishers and snow mobiles. The house is great! Might want to get the lighting a bit more finessed- superbright, cold lights here and there, in and outside, mess with the Cozy winter night vibes. "
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!

40 private acres of Lakefront Adirondack Paradise

9.8 out of 10, Exceptional, (49)
"We had a great stay, and Karen was a pleasure to deal with. She was responsive and and clear in her communications, and her check in and check out processes are easy and straightforward. The house was very comfortable and clean, and is in a beautiful setting."
40 private acres of Lakefront Adirondack Paradise

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

7.6 out of 10, Good, (24)
"The cabin and the outside property (other than the driveway which needs attention) we’re great, The cabin is old and needs some upgrades but was perfect for our stay with the grandchildren. We loved that clean bed linens and plenty of towels were provided. The kitchen worked fine for us and happy plates, silverware, etc were provided. We loved the outside fire pit (great for s’mores) and the view and access to the lake was great, The granddaughters went fishing off the 20 foot dock and caught...
Dog-friendly cabin with lakefront location, 20' dock, smart TV

Peaceful retreat in the heart of the Adirondacks.

10.0 out of 10, Exceptional, (7)
"The house was beautiful and very clean. It was also well stocked with lots of appliances and an ice machine! We thoroughly enjoyed our stay and would recommend!"
Peaceful retreat in the heart of the Adirondacks.

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

9.6 out of 10, Exceptional, (12)
"The location was great for our motorcycle rides around the Adirondacks."
2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C
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.
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Frequently asked questions

What's the best pet-friendly hotel in Chestertown?
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is a top pet-friendly option for your stay. Pine Tree Motel & Cabins 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.