An aerial view of a town with a river, buildings, and surrounding greenery.

Pet friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Pet friendly Hotels

Tonight
Aug 15 - Aug 16
Tomorrow
Aug 16 - Aug 17
Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30

Our top choices for Chestertown pet-friendly hotels

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Anna
P6,378
P7,080 total
includes taxes & fees
Sep 13 - Sep 14
Comfort Inn & Suites Chestertown

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Anasmel
P3,871
P4,297 total
includes taxes & fees
Aug 23 - Aug 24
Red Roof Inn & Suites Chestertown

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Daryl
P3,902
P4,332 total
includes taxes & fees
Aug 17 - Aug 18
Driftwood Inn

4. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Jackie
P7,743
P8,594 total
includes taxes & fees
Sep 14 - Sep 15
Holiday Inn Express Annapolis East-Kent Island by IHG

5. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Mark
P5,996
P6,716 total
includes taxes & fees
Aug 30 - Aug 31
Home2 Suites by Hilton Baltimore / Aberdeen, MD

6. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
P5,190
P5,813 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn & Suites Edgewood/Aberdeen-South

7. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Joan
P9,866
P11,050 total
includes taxes & fees
Aug 20 - Aug 21
Vandiver Inn

8. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
chanel
P7,406
P8,221 total
includes taxes & fees
Aug 23 - Aug 24
Best Western Kent Narrows Inn
View all properties

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Wonderful view of the water and bay. Convenient walk to downtown Annapolis and area. Room was impeccable."
Ronnie 1-night trip
Posted 2 hours ago
Annapolis Waterfront Hotel, Autograph Collection
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent
"The room was clean. I bit noisy, but not the fault of the hotel."
Timothy 1-night trip
Posted 17 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"The door into the building from the parking lot is always locked, which is great, because it cannot be seen from the front desk, but it is difficult to enter with the room key. The key is a typical credit card-like key, but the electronic reader was wonky. Sometimes it worked and sometimes it didn’t. The cards worked well on the room doors but not on the entrance door. It was an inconvenience to walk around the building to get it the main entrance if the card did not work."
Mary Ellen 2-night trip
Posted 1 day 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 Chestertown Historic District and Northern Chesapeake Bay. While you're there, make sure you don't miss Chesapeake Bay and Historical Society of Kent County Maryland.

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