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Find Pet-friendly Hotels in Chestertown, MD

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Check availability on Chestertown Pet-friendly Hotels

Tonight
2 Jun - 3 Jun
Tomorrow
3 Jun - 4 Jun
This weekend
6 Jun - 8 Jun
Next weekend
13 Jun - 15 Jun

Top Chestertown Pet-friendly Hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (767)
"The breakfast was consistently tasty."
The price is AED 424
AED 470 total
includes taxes & fees
15 Jun - 16 Jun
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (362)
"Was a decent place to stay for the price. "
The price is AED 251
AED 279 total
includes taxes & fees
10 Jun - 11 Jun
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

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"
Driftwood Inn
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

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

10.0 out of 10, Exceptional, (1)
"My family and I had the best time at the Outrange. The house is super cool. But the access to hiking, kayaking and even goats made it perfect. Ben is super good at communication. He responded to any of my questions quickly. I can't say enough about it. Just a really lovely property. "
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.8 out of 10, Exceptional, (8)
"Property was in great shape. Great view of the water and all had a great time!"
Pet-Friendly Home on Chester River w/ Dock!
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

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

10.0 out of 10, Exceptional, (77)
"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!
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

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
Country Estate in Historic District
Fridge, microwave, oven, stovetop

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
Outdoor pool

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!
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.

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 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.