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Pet friendly Hotels in Chestertown, Maryland

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Top Chestertown Pet friendly Hotels

Comfort Inn & Suites Chestertown
Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (727)
"Was there just one night and didn't eat breakfast, but staff were wonderful and the room seemed newly renovated. Room was large and clean with coffee maker and mini-fridge. "
The price is P6,301
P6,994 total
includes taxes & fees
Dec 22 - Dec 23
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (320)
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price."
The price is P4,407
P4,892 total
includes taxes & fees
Dec 23 - Dec 24
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby
Driftwood Inn
2.0 star property
5.0 out of 10, (167)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is P3,742
P4,154 total
includes taxes & fees
Nov 23 - Nov 24
Driftwood Inn
Pet-friendly Home on Chester River w/ Dock!
Interior
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.
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Frequently asked questions

What's the best pet-friendly accommodation in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers a fitness center and laundry facilities for its human guests. Other good choices for you and your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn.
How many hotels that accept pets can I expect to find in Chestertown?
Stay 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 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
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 Rolphs Wharf Marina and Historical Society of Kent County Maryland. While you’re there, make sure you don’t miss Garfield Center for the Arts at the Prince Theater and Wilmer Park.