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

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Check availability on Chestertown Pet-Friendly Hotels

Tonight
11 Sept - 12 Sept
Tomorrow
12 Sept - 13 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

Our top choices for Chestertown pet-friendly hotels

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

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
₹9,923
₹11,014 total
includes taxes & fees
4 Oct - 5 Oct
Comfort Inn & Suites Chestertown
Exterior
Desk, laptop workspace, blackout curtains, iron/ironing board
Lobby lounge
Exterior

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
₹6,847
₹7,600 total
includes taxes & fees
17 Sept - 18 Sept
Red Roof Inn & Suites Chestertown
Front of property – evening/night
Room | Desk, soundproofing, free WiFi, bed sheets
Front of property
Lobby

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
₹6,039
₹6,704 total
includes taxes & fees
13 Sept - 14 Sept
Driftwood Inn
Exterior
Free daily buffet breakfast
Exterior
Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Emily
₹11,263
₹12,502 total
includes taxes & fees
6 Oct - 7 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
Reception
King suite whirlpool | Bathroom | Combined shower/bathtub, free toiletries, hair dryer, towels
Two queen studio suite | Bathroom | Combined shower/bathtub, free toiletries, hair dryer, towels
Pool

5. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
₹8,062
₹9,029 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South
Standard Room, 1 Queen Bed, Non Smoking, Refrigerator & Microwave | In-room safe, desk, laptop workspace, iron/ironing board
Indoor pool
Lobby
Property amenity

6. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Joshua
₹11,103
₹12,325 total
includes taxes & fees
28 Sept - 29 Sept
Best Western Kent Narrows Inn
Terrace/patio
Marina
Exterior
Lobby

7. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
₹14,508
₹16,104 total
includes taxes & fees
4 Oct - 5 Oct
Hyatt Place Kent Narrows & Marina
Exterior
Lobby
Property amenity
Lobby

8. La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
United States
Niall
₹10,652
₹11,930 total
includes taxes & fees
12 Sept - 13 Sept
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Reception
Breakfast and dinner served
Reception
Exterior

9. Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
Aberdeen
United States
Philip
₹10,451
₹11,705 total
includes taxes & fees
24 Sept - 25 Sept
Hilton Garden Inn Aberdeen
View all properties

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"The location was great. We were able to walk everywhere. Considering the price of rooms, the $39 parking fee was high."
Gary 1-night trip
Posted 1 day ago
Annapolis Waterfront Hotel, Autograph Collection

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 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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