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

Find Pet-friendly Hotels in Chestertown, MD

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Check availability on Chestertown Pet-friendly Hotels

Tonight
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Chestertown pet-friendly hotels

Free daily full breakfast
Point of interest
Lobby
Desk, laptop workspace, blackout drapes, iron/ironing board

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Deanna
₩148,561
₩164,902 total
includes taxes & fees
Sep 14 - Sep 15
Comfort Inn & Suites Chestertown
Exterior
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Exterior
Exterior

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
₩87,307
₩96,911 total
includes taxes & fees
Aug 30 - Aug 31
Red Roof Inn & Suites Chestertown
Front of property - evening/night
Front of property
TV
Lobby

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Daryl
₩88,000
₩97,687 total
includes taxes & fees
Aug 25 - Aug 26
Driftwood Inn
Exterior
Free daily buffet breakfast
Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board
Exterior

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Jackie
₩176,000
₩195,360 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Free daily buffet breakfast
Exterior
Indoor pool

5. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Mark
₩135,229
₩151,457 total
includes taxes & fees
Aug 30 - Aug 31
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Reception
Two queen studio suite | Bathroom | Combined shower/tub, free toiletries, hair dryer, towels
King suite whirlpool | Bathroom | Combined shower/tub, free toiletries, hair dryer, towels
Reception

6. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
₩115,911
₩129,821 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior detail
Dining
Room, Private Bathroom (Tydings) | Premium bedding, memory foam beds, desk, iron/ironing board
Exterior

7. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Joan
₩222,495
₩249,195 total
includes taxes & fees
Aug 27 - Aug 28
Vandiver Inn
Indoor pool
Exterior
Exterior
In-room safe, desk, laptop workspace, iron/ironing board

8. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
chanel
₩176,347
₩195,745 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Kent Narrows Inn
View all properties

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"Balcony was great so was the view, hotel getting a little old needs some room cosmetics, location great"
Jan 1-night trip
Posted 20 hours ago
Annapolis Waterfront Hotel, Autograph Collection

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 Garfield Center for the Arts at the Prince Theater and Chestertown Historic District. While you're there, make sure you don't miss Northern Chesapeake Bay and Chesapeake Bay.

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