Photo by Julie Miller

Find Pet-friendly Hotels in Chestertown, NY

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Pet-friendly Hotels

This weekend
Next weekend

Top Chestertown Pet-friendly Hotels

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (137)
"Excellent location and staff was very friendly."
The price is AED 643
AED 713 total
includes taxes & fees
2 Sep - 3 Sep
Pine Tree Motel & Cabins

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

10.0 out of 10, Exceptional, (35)
"The propety was perfect for a family with several beds, two bathrooms, a huge backyard and thr family favorite hot tub. Plenty of privacy. Close to many amenities and lots of lakes!"
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, (68)
"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

#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!

40 private acres of Lakefront Adirondack Paradise

9.8 out of 10, Exceptional, (53)
"Our family had a great vacation at this property! From the pond to the fire pit to the home itself, it was wonderful. Great proximity to Lake George too!"
40 private acres of Lakefront Adirondack Paradise

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very Good, (45)
"It is an older house with a lot of character. For our very large family. The pool was super clean and a hit with everyone. Very convenient to lake George, and having a grocery store a very short walk away was a huge bonus!"
Elizabeth. A Guest House Near Lake George.

#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

8.6 out of 10, Excellent, (10)
"We had a great weekend get away much thanks to Margo for accommodating us on short notice. Enjoyed the cabin , the evening fires , the grounds were well kept , got some great photos kayaking with the lions . Very nice stay would definitely recommend and return ."
#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

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

7.6 out of 10, Good, (27)
"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

A beautiful lake view cabin on Friends Lake

9.6 out of 10, Exceptional, (51)
"Another wonderful relaxing stay. So happy to have spent another week here. And same as last year every thing went smoothly and we had a great time exploring and visiting with family. Thank you Amanda for another great stay!"
A beautiful lake view cabin on Friends Lake

#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

9.6 out of 10, Exceptional, (12)
"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!
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.

Top Chestertown Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia