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

Pick from 34 Chestertown Pet-friendly Hotels and compare 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, (125)
"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
Living area
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
10.0 out of 10, Exceptional, (24)
"What an adorably cute, warm, welcoming location so glad we picked this place. Everything was clean the beds were comfortable and the neighborhood completely safe. "
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Great Room
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10.0 out of 10, Exceptional, (53)
"Host John was like best of friends. Couldn’t have done more for us. Sue too was very nice. Pearl and ruby, their do"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Dog-friendly cabin with lakefront location, 20' dock, smart TV
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
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
Adirondack Log cabin on 30 acres
New kelm living
Adirondack Log cabin on 30 acres
9.4 out of 10, Exceptional, (35)
"Amazing house, very quiet and secluded, just what we needed. Wonderful host, would highly recommend!"
Adirondack Log cabin on 30 acres
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Exterior
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
9.6 out of 10, Exceptional, (15)
"Very nice just terrain was rough handicap person"
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
Lodge and front yard
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
9.8 out of 10, Exceptional, (47)
"Prefect for our family of 12. Plenty of room to enjoy each other. The host was very attentive. We looking forward to staying there again in the future."
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
40 private acres of Lakefront Adirondack Paradise
Northern lights on our lake
40 private acres of Lakefront Adirondack Paradise
9.8 out of 10, Exceptional, (45)
"The property is absolutely beautiful. It’s private and quiet. Swimming, fishing, boating, shopping and history. It was a great trip! Already looking into next year!"
40 private acres of Lakefront Adirondack Paradise
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Swim area. What a view!
#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

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.