Photo by Assya A

Find Pet-friendly Hotels in Chestertown, MD

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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.

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (760)
"Staff was efficient and very helpful. Clean room with microwave & fridge - well stocked linens in bathroom - great breakfast - thank you for a comfortable stay."
The price is AED 403
AED 447 total
includes taxes & fees
18 May - 19 May
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (349)
"Easy to get to, food all around!"
The price is AED 251
AED 279 total
includes taxes & fees
13 May - 14 May
Red Roof Inn & Suites Chestertown

Driftwood Inn

2.0 star property
5.2 out of 10, (170)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is AED 233
AED 259 total
includes taxes & fees
20 May - 21 May
Driftwood Inn

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

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

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (5)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!

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

9.8 out of 10, Exceptional, (80)
"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."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

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

10.0 out of 10, Exceptional, (76)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Country Estate in Historic District

10.0 out of 10, Exceptional, (67)
"Great stay!"
Country Estate in Historic District

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

10.0 out of 10, Exceptional, (61)
"Great!"
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.
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Frequently asked questions

What's the best pet-friendly accommodation in Chestertown?
Red Roof Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers laundry facilities and free newspapers for its human guests. Other good choices for you and your pet include Comfort 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 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 Urieville Park.