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Find Pet-friendly Hotels in Chestertown, MD

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Check availability on Chestertown Pet-friendly Hotels

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Top Chestertown Pet-friendly Hotels

Our top choices for Chestertown pet-friendly hotels

Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (90)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is ￥22,916
￥25,437 total
includes taxes & fees
Sep 25 - Sep 26
Mariners Motel
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1005)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is ￥13,049
￥14,615 total
includes taxes & fees
Sep 29 - Sep 30
Hampton Inn & Suites Edgewood/Aberdeen-South
Vandiver Inn
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (518)
"Been to the Vandiver many times and are always pleasantly pleased."
Vandiver Inn
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (820)
"Friendly staff, clean room, convenient location. "
The price is ￥16,529
￥18,348 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, (396)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is ￥11,299
￥12,542 total
includes taxes & fees
Sep 30 - Oct 1
Red Roof Inn & Suites Chestertown
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (283)
"Friendly staff, comfortable bed and clean room "
The price is ￥15,351
￥17,040 total
includes taxes & fees
Oct 19 - Oct 20
Fairfield Inn & Suites by Marriott Middletown
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (834)
"Decent for a Hampton Inn"
The price is ￥16,196
￥17,977 total
includes taxes & fees
Sep 30 - Oct 1
Hampton Inn Middletown
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (902)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is ￥19,927
￥22,118 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Annapolis East-Kent Island by IHG
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.0 out of 10, Wonderful, (1013)
"Loved our stay! Will visit again soon!!! "
The price is ￥13,174
￥14,756 total
includes taxes & fees
Oct 5 - Oct 6
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very Good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is ￥27,460
￥33,757 total
includes taxes & fees
Sep 29 - Sep 30
Inn at Haven Harbour
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.
View all properties

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Y"
Alexander 3-night trip
Posted 7 days ago
Annapolis Waterfront Hotel, Autograph Collection

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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 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.