Photo by Julie Miller

Find Pet-friendly Hotels in Chestertown, NY

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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
Exterior

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
Smart TV, fireplace, foosball, books

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

10.0 out of 10, Exceptional, (30)
"Perfect location for our ski trip to gore mountain. Close to all the necessities. House had everything we needed and more! Beautiful spaces and rooms, great property! Perfect rural getaway. "
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, (60)
"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
Rustic Adirondacks Home w/ Hot Tub & Lake Access!
Exterior

Rustic Adirondacks Home w/ Hot Tub & Lake Access!

10.0 out of 10, Exceptional, (21)
"It was perfect for the short time we had there."
Rustic Adirondacks Home w/ Hot Tub & Lake Access!
Elizabeth. A Guest House Near Lake George.
Lake

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.
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)
"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
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)
"We went for a weekend ski trip to Gore with friends. This cabin is located a quick 20 min drive from the mountain; just right. The cabin was very clean on arrival.The property was advertised with a hot tub which influenced or decision to book this property. When we arrived the hot tub was broken, there was a sign at check in apologizing for the inconvenience, and stating a partial refund for the malfunction was already initiated. Stuff happens, we understood, but it has been a few weeks and no...
2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C
40 private acres of Lakefront Adirondack Paradise
Exterior

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
Secluded and Cozy Townhome near Tripp Lake
Interior

Secluded and Cozy Townhome near Tripp Lake

10.0 out of 10, Exceptional, (101)
"We had a wonderful time staying here. We came in for a wedding and it was a very nice place to stay and relax. We would come again!"
Secluded and Cozy Townhome near Tripp 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, (11)
"Arrived around 5 on Saturday. Great location. Once I figured out how to open key holder, we moved in. We enjoyed our cabin, found the information folders helpful. We had a nice fire and enjoyed our stay. Our suggestions for improvement. The light in the main room was very bright. A dimmer light switch would have been appreciated. Would like to have had a reading light on both sides of the bed."
#2 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.
Don't see what you're looking for?
See all available properties in Chestertown

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 Friends Lake and Loon Lake. While you’re there, make sure you don’t miss Hudson River and Loon Lake Beach.