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Find Pet-friendly Hotels in Chestertown, MD

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Check availability on Chestertown Pet-friendly Hotels

Top Chestertown Pet-friendly Hotels

Our top choices for Chestertown pet-friendly hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (817)
"Friendly staff, clean room, convenient location. "
The price is ₩159,715
₩177,284 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (395)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is ₩105,290
₩116,871 total
includes taxes & fees
Sep 24 - Sep 25
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
The price is ₩87,408
₩97,030 total
includes taxes & fees
Oct 14 - Oct 15
Driftwood Inn
Pet-friendly Home on Chester River w/ Dock!
House (4 Bedrooms) | 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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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"We came here for a birthday weekend away with our family of 6. From the minute we got there we were greeted by this very sweet girl, Amber. She was very friendly and got us everything we needed without even being asked including the extra sheets for the pull out and getting a big cart for us. The room was very clean and breakfast was delicious. We will definitely be back. "
Kristina 2-night trip
Posted 4 days ago
Comfort Inn & Suites Chestertown

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 seasonal outdoor pool and a fitness center for its human guests. Other good choices for you and your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn.
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.