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Chestertown Hotel Guide - Pet Friendly Hotels in Chestertown, New York

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Top Chestertown Pet Friendly Hotels

Our top choices for Chestertown pet-friendly hotels

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 €164
includes taxes & fees
1 Oct - 2 Oct
Pine Tree Motel & Cabins

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

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

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!

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!

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.

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

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!

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

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.

Top Chestertown Hotel Reviews

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Frequently asked questions

What's the best dog-friendly accommodation option in Chestertown?
Pine Tree Motel & Cabins is a top dog-friendly option for your stay. Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is another good option if you're bringing your pet along.
What's the best time of year to travel to Chestertown with my pet?
When you're travelling with pets, keeping track of the weather can make the trip safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm 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.