Photo by Julie Miller

Find Pet-friendly Hotels in Chestertown, NY

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Check availability on Chestertown Pet-friendly Hotels

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Compare Chestertown Pet-friendly Hotels room rates, reviews, and availability. Most hotels are fully refundable.

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

10.0 out of 10, Exceptional, (26)
"The house was beautiful with spacious living and dining areas. The 3 season screen room was nice, though we stayed in January and didn’t get to enjoy it. The kids and husband enjoyed the foosball table and arcade game. The master bed room is in the basement and the kids room downstairs, but there is an alarm/chime in place that goes off when any door opens which put my mind at ease being on another floor. Other reviews said the basement is cold but I did not find that to be true. There are local...
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, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Adirondack Log cabin on 30 acres

9.6 out of 10, Exceptional, (37)
"Beautiful cabin. Very peaceful and quiet "
Adirondack Log cabin on 30 acres

Spacious and Cozy Adirondack Home Just Minutes to Lake George and Gore Mountain

Spacious and Cozy Adirondack Home Just Minutes to Lake George and Gore Mountain

Winter in the Adirondacks

9.8 out of 10, Exceptional, (49)
"We really enjoyed our stay here. The lake was warm and had a sandy entry which the kids enjoyed. You could paddle board or kayak to the public beach which was also fun. The house was comfortable with ample room for everyone and AC in all the bedrooms. I do think it’s important to note that the house is on a road with a high speed limit and some traffic which I didn’t realize from the pictures. It was fine for us but might be hard with small children. We had a great time and would definitely...
Winter in the Adirondacks

Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!

9.8 out of 10, Exceptional, (51)
"We stayed for a winter holiday weekend and were charmed by the view of the frozen-over Loon Lake with its ice fishers and snow mobiles. The house is great! Might want to get the lighting a bit more finessed- superbright, cold lights here and there, in and outside, mess with the Cozy winter night vibes. "
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!

40 private acres of Lakefront Adirondack Paradise

9.8 out of 10, Exceptional, (47)
"Loved every bit of it. Quiet, peaceful, clean, well equipped. The host had a Christmas tree up as well as decorations in every room. An unexpected and beautiful surprise."
40 private acres of Lakefront Adirondack Paradise

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-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
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.
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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.
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.