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Pet Friendly Hotels & Resorts in Chestertown from NZ$117

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Check availability on Chestertown Pet Friendly Hotels

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Best Chestertown Pet Friendly Hotels

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (787)
"Place was very helpful getting me acclimated to the new area and they were very friendly to my pup!"
Joe
The price is NZ$210
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (380)
"Terrible staff attitudes. Crappy room - fridge, ac, tv didn’t work. Whole place stunk. Sorry, we needed a
pet friendly
for our puppy and we knew it’s not a 3-4 star place but I can’t wait to get home to shower. P.S. I never write a review…."
Susan
The price is NZ$141
includes taxes & fees
5 Aug - 6 Aug
Red Roof Inn & Suites Chestertown

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
Quiana
The price is NZ$117
includes taxes & fees
27 July - 28 July
Driftwood Inn

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (5)
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (83)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a
dog
-friendly place too. Great and prompt communication with the hosts."
Sun P.
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (11)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Tori
Pet-Friendly Home on Chester River w/ Dock!

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (81)
"It was our second time staying. The house is lovely with lots of homey touches--books, games, throw blankets. And the grounds are lovely -- a big yard right on the river. We loved kayaking and letting our
dog
explore the yard and the river front. The kitchen is well stocked (but if you have a favorite pan you might want to bring that). The screened in porch was a favorite place to eat and play games looking at the beautiful view. I hope we can return some time soon."
Karin C.
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Country Estate in Historic District

10.0 out of 10, Exceptional, (69)
"Everything about this property is perfection. It’s like walking into a brand new 1920s house. The charm is all there in spades, but the woodwork and hardware are in mint condition throughout. It’s the most perfectly kept old house I’ve ever stayed in. All that, but there are modern touches, too. The kitchen is huge and well stocked, and the main bath has a huge jacuzzi tub. Our
dog
had a blast running around the large park-like yard. The house is close to everything in town. The hosts were...
Kyle W.
Country Estate in Historic District

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"The property amenities were terrific including the sports court, pool and the river access including the canoe, kayaks and paddle boards. The privacy of the property and walks to the dock were enjoyed by the family and our
dogs
. Boys enjoyed fishing off the dock as well. The house is a bit older as seen in the pictures but the kitchen and family room were spacious and we enjoyed many meals, board games and card games around the kitchen table. Bring your bug spray for your family and
pets
as...
Sherri A.
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Pet-friendly Home on Chester River w/ Dock!

3.0 star property
Pet-friendly Home on Chester River w/ Dock!
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 dog-friendly accommodation option in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Two other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn.
How many hotels that welcome pets should I expect to find in Chestertown?
Stay with your furry friend at one of Expedia's 5 pet-friendly Chestertown hotels or accommodation options.
What's the best time of year to travel to Chestertown with my pet?
When you travel with your pet, keeping tabs on the weather can make the trip safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What is there to see and do with your pet in Chestertown?
Known for its sports, Chestertown has lots to offer visitors, including its university life and festivals. See the local sights and visit Historical Society of Kent County Maryland and Rolphs Wharf Marina. While you're there, make sure you don't miss Garfield Center for the Arts at the Prince Theater and Chestertown Historic District.