Cat & Dog Friendly Hotels in Chestertown

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Our top choices for Chestertown pet-friendly hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (861)
"Everything was well!"
United States
Ahmed
The price is RM404
RM449 total
includes taxes & fees
25 Jan - 26 Jan 2026
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (423)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is RM292
RM324 total
includes taxes & fees
4 Jan - 5 Jan 2026
Red Roof Inn & Suites Chestertown

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (683)
"friendly staff, clean room / lobby, nice bar, everything was great"
United States
William
The price is RM470
RM522 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Kent Narrows & Marina

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (942)
"It was very comfortable and clean"
United States
Maria
The price is RM320
RM355 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (325)
"Clean room, great staff, recommended. "
United States
Tom
The price is RM437
RM486 total
includes taxes & fees
5 Jan - 6 Jan 2026
Fairfield Inn & Suites by Marriott Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (868)
"Amazing stay"
United States
Katiana
The price is RM385
RM428 total
includes taxes & fees
13 Jan - 14 Jan 2026
Hampton Inn Middletown

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (606)
"very pet friendly!!"
United States
larry
The price is RM397
RM445 total
includes taxes & fees
10 Jan - 11 Jan 2026
Hampton Inn & Suites Baltimore/Aberdeen

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh
3.0 star property
Nottingham
7.8 out of 10, Good, (1006)
"Very nice place to stay"
United States
Tina
The price is RM427
RM493 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Baltimore/White Marsh

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1002)
"Nice place"
United States
Maria
The price is RM361
RM405 total
includes taxes & fees
4 Jan - 5 Jan 2026
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG
3.0 star property
Belcamp
8.4 out of 10, Very good, (741)
"the room was spotless and the breakfast was very nice."
United States
Carl
The price is RM288
RM322 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Belcamp - Aberdeen Area by IHG
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.

Top Chestertown Hotel Reviews

Frequently asked questions

What's the best dog-friendly accommodation option in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Two other good options to stay with 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 Northern Chesapeake Bay. While you're there, make sure you don't miss Chesapeake Bay and Chestertown Historic District.

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