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Check availability on Chestertown Pet-friendly Hotels

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Top Chestertown Pet-friendly Hotels

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (130)
"Wonderful friendly owners and probably the cleanest place I’ve ever stayed! And they are
dog
friendly! "
James
The price is SAR 657
SAR 729 total
includes taxes & fees
28 Jul - 29 Jul
Pine Tree Motel & Cabins

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

10.0 out of 10, Exceptional, (34)
"The house was perfect for our Easter weekend with family. Very clean, kitchen is fully equipped, the house is well located if you want to go hiking in the area. The hosts were very responsive and very thoughtful! They even gave us bowls for the
dog
! I highly recommend."
Coline H.
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, (62)
"So much more than we expected.The best of both worlds Camping in luxury. Susan and John were so nice, friendly and accommodating. Our
dogs
loved playing with Ruby and Pearl. If we needed anything they had it. We wished we were still there. Absolutely going next year staying a week for sure.Thank you, this is just what my family needed."
RaeAnne P.
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."
Heather
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very Good, (42)
"I can't say enough great things about our time in the Adirondacks! Our host was a pleasure to work with and responded to messages very quickly. The house was exactly as described. Plenty of room for everyone in our party. I don't have
pets
but people in my party brought their
dogs
. I loved that the rental was
pet friendly
, but I wasn't aware that other animals had been there. The kitchen was clean and had everything we needed. I loved that everything we needed was right there, not just...
Laura H.
Elizabeth. A Guest House Near Lake George.

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

7.6 out of 10, Good, (24)
"If you are looking for a fancy, large, elaborate lake house, this isn't it. If you are looking for a cozy, comfortable, family friendly (including your 4 legged family) lake house this is it. This was our 2nd summer with a week long rental at this house and we had a great time this year too. We had a few issues (wrong key code to lock box sent to us, told there was a new grill but the dangerous grill from last year was still there) but Vacasa reimbursed us for the inconvenience. Most likely will...
Jodie J.
Dog-friendly cabin with lakefront location, 20' dock, smart TV

A beautiful lake view cabin on Friends Lake

9.6 out of 10, Exceptional, (50)
"Overall the cabin was great and as described. We enjoyed the lake, use of the kayaks, and sitting by the fire both inside and out. The pups enjoyed their time too. Amanda was great with information and answers to our questions. We had a hiccup from Mother Nature and Amanda was very communicative about it. Luckily for us, the power was turned on right before we arrived. Bed was comfortable. Shower is quite small especially for women who need to shave. Cell reception and wifi wasn’t the greatest....
Kristie B.
A beautiful lake view cabin on Friends Lake

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

9.6 out of 10, Exceptional, (12)
"We booked a last minute trip and was not disappointed! The private, fully furnished cabin was perfect for our weekend get away. They also have boats, kayaks, paddle boards and so much more down at the beach free to use. The manager was so quick to respond to our questions/concerns and the check in/check out was SO simple. We definitely found our new place to go yearly, highly recommend!"
Victoria R.
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

Great Adirondacks retreat with five bedroomsHot tub,pool table.large open space

8.6 out of 10, Excellent, (7)
"We loved everything about our stay and the accommodations The Hot Tub was a big hit as well as the fireplace.The kitchen had what we needed.The Outside Grill gave us the perfect Burger we only missed the Towels and not sure if I missed that on the listing we had three towels We would recommend this place to everyone Will definitely Re"
Michael F.
Great Adirondacks retreat with five bedroomsHot tub,pool table.large open space

Secluded and Cozy Townhome near Tripp Lake

10.0 out of 10, Exceptional, (102)
"We had an excellent stay on Tripp Lake. The accommodations were very comfortable, clean and quiet in a convenient location. Would gladly do this again. "
Richard K.
Secluded and Cozy Townhome near Tripp 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

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.