Photo by Julie Miller

Find Pet-friendly Hotels in Chestertown, NY

Start date: Check-in selected.
To Date
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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Pet-friendly Hotels

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Top Chestertown Pet-friendly Hotels

Our top choices for Chestertown pet-friendly hotels

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (141)
"Excellent location and staff was very friendly."
The price is ￥25,832
￥28,673 total
includes taxes & fees
Sep 25 - Sep 26
Pine Tree Motel & Cabins
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Sun loungers

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

10.0 out of 10, Exceptional, (35)
"Property was accommodating and presented the same as you see in the display pictures. The owners have made it inviting for a family along with ensuring there is enough technology and recreational items to entertain through all ages. We highly recommend staying here and plan to in the future if we return to the area."
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, (69)
"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
Lakefront Adirondack Paradise on 40 acres
Exterior

Lakefront Adirondack Paradise on 40 acres

9.8 out of 10, Exceptional, (56)
"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!"
Lakefront Adirondack Paradise on 40 acres
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
On the beach

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

9.6 out of 10, Exceptional, (17)
"The views were absolutely amazing! We will definitely be back."
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
#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, (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!
Elizabeth. A Guest House Near Lake George.
Lake

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

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

7.6 out of 10, Good, (27)
"Location on lake was nice, dock for swimming, fishing, etc. Bedding and towels were clean. Could use some updates."
Dog-friendly cabin with lakefront location, 20' dock, smart TV
#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Exterior

#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!
A beautiful lake view cabin on Friends Lake
Property grounds

A beautiful lake view cabin on Friends Lake

9.6 out of 10, Exceptional, (53)
"Nice place. Had a good time."
A beautiful lake view cabin on Friends Lake
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.
View all properties

Top Chestertown Hotel Reviews

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"We love the Queensbury! We've stayed several times and the hotel is always so accommodating in giving us our favorite room. We enjoyed a delicious dinner outside at Park 26. The decor and ambiance is wonderful and the staff are always friendly and courteous. Parking is great and the hotel is conveniently situated to walk into town. The Queensbury is our first (only) choice when visiting the Lake George area."
Suzanne 1-night trip
Posted 6 days ago
The Queensbury Hotel
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

10/10 Excellent
"Came here for the weekend with my husband and my dog! The place is really nice, clean "
Lidia 2-night trip
Posted 3 weeks ago
Pine Tree Motel & Cabins

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.
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.