Photo by Julie Miller

Pet Friendly Hotels & Resorts in Chestertown

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Best Chestertown Pet Friendly Hotels

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, (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
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
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
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
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!
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!
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
9.8 out of 10, Exceptional, (46)
"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!
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.
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Beautiful view of the beach with palm trees

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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.
How many hotels that accept pets will I find in Chestertown?
Enjoy travelling with your furry pal at one of Expedia’s 5 Chestertown accommodation options that accept pets.
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.