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

Chestertown Hotel Guide - Pet Friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Pet Friendly Hotels

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

Our top choices for Chestertown pet-friendly hotels

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A modern lounge area with seating, a fireplace, and a television.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.
A hotel room with two beds, a desk, a TV, and a window with curtains.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
€103
includes taxes & fees
22 Sept - 23 Sept
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a desk, and a painting on the wall.
A hotel room with a bed, a desk, a chair, a sofa, and a painting on the wall.
A multi-story brick building with a covered entrance and a parking lot.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
€67
includes taxes & fees
30 Aug - 31 Aug
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.
A living room with a wooden cabinet, a television, a sofa, and a dining table.
A two-story building with a brick facade, large windows, and a sloped roof.

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Vanesa
€60
includes taxes & fees
30 Aug - 31 Aug
Driftwood Inn
A park with a curved wooden bridge, a tree with purple blossoms, and a grassy area.
A kitchen with a central island, wooden cabinets, a ceiling fan, and a dining area with a chair and rug.
A porch with a red door, a bench, and potted plants.
A wooden cabinet with glass doors, a red carpet, and a patterned rug in a hallway.

4. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
United States
Mandy D.
€441
includes taxes & fees
29 Sept - 30 Sept
Wren Retweet- Country Estate in Center of C’Town
Two Adirondack chairs facing a calm body of water with a clear sky above.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Betty
€116
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
A multi-story hotel with a modern facade, featuring a prominent 'HOME 2' sign. The entrance is accessible via a covered walkway, and the building is equipped with large windows and a flagpole.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
A modern restaurant with a bar area, seating, and a counter with a menu display.

6. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Mark
€94
includes taxes & fees
7 Sept - 8 Sept
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.
A cozy living room with a sofa, armchair, and a fireplace.
A formal dining room with a long table, chairs, a chandelier, and a fireplace.
A bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.

7. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Joan
€154
includes taxes & fees
13 Sept - 14 Sept
Vandiver Inn
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

8. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
€81
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South
A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A restaurant with a counter, seating area, and a clock on the wall.

9. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
chanel
€111
includes taxes & fees
28 Sept - 29 Sept
Best Western Kent Narrows Inn
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

10. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
€159
includes taxes & fees
8 Sept - 9 Sept
Hyatt Place Kent Narrows & Marina
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Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"The location of the hotel was awesome along with our balcony view. However you should not have to pay an additional $50 per day to park your car especially since the garage up the street is Therefore the guests are getting pentalized to park at the hotel . Additionally the front desk women were rude and condescending"
Michele 2-night trip
Posted 3 days 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.