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Find Pet-friendly Hotels in Chestertown, MD

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Check availability on Chestertown Pet-friendly Hotels

Compare Chestertown Pet-friendly Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (749)
"It was fine and served our needs."
The price is SAR 390
SAR 432 total
includes taxes & fees
20 Apr - 21 Apr
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, (338)
"I loved the decor of my room. The king size bed was cozy. "
The price is SAR 233
SAR 258 total
includes taxes & fees
28 Mar - 29 Mar
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.0 out of 10, (168)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is SAR 238
SAR 264 total
includes taxes & fees
28 Mar - 29 Mar
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!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
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, (75)
"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!
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"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
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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
Carriage House Hideaway in Middle of Chestertown
Iron/ironing board, travel crib, free WiFi, bed sheets

Carriage House Hideaway in Middle of Chestertown

10.0 out of 10, Exceptional, (86)
"Very sweet studio with everything you need for your stay. Extremely quiet and walking distance to great restaurants and shops. Hosts were very gracious and available if needed. We definitely will book again. Thank you!"
Carriage House Hideaway in Middle of Chestertown
Country Estate in Historic District
Fridge, microwave, oven, stovetop

Country Estate in Historic District

10.0 out of 10, Exceptional, (66)
"Wow! This house is beautiful. A gem of old and new areas with lovely finishes and lots of space, each of us four guests had our own bedroom. The owners have supplied this domicile with every amenity one could imagine. It was well stocked with towels, paper products, kitchen tools and wonderful appliances. On the island stood a welcoming bottle of wine. Having enjoyed our stay so much, We may be returning next year! "
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
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 Urieville Park.