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
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

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 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.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
฿3,516
฿3,903 total
includes taxes & fees
16 Sept - 17 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.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
฿2,296
฿2,548 total
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 two-story building with a brick facade, large windows, and a sloped roof.
A living room with a wooden cabinet, a television, a sofa, and a dining table.

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Vanesa
฿2,076
฿2,304 total
includes taxes & fees
30 Aug - 31 Aug
Driftwood Inn
Two Adirondack chairs facing a calm body of water with a clear sky above.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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 reception desk with a modern design, a digital display, and a check-in counter.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Betty
฿4,151
฿4,608 total
includes taxes & fees
9 Sept - 10 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.
A hotel room with a desk, office chair, sofa, and a dining table with chairs. There is a window with blinds, a painting on the wall, and a door leading to another room.
A modern restaurant with a bar area, seating, and a counter with a menu display.

5. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Mark
฿3,190
฿3,572 total
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 bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.
A formal dining room with a long table, chairs, a chandelier, and a fireplace.
A traditional house with a covered porch, white picket fence, and lush greenery.

6. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Joan
฿5,266
฿5,898 total
includes taxes & fees
9 Sept - 10 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 room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

7. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
฿2,743
฿3,072 total
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South
A swimming pool with a mural, lounge chairs, and a hot tub.
A modern interior with a dining area, kitchen, and living space.
A hotel room with a large bed, a separate sitting area, a bathtub, and a view of the outdoors.
A multi-story hotel with a central courtyard, a flag, and a sign indicating it is a Radisson hotel.

8. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
chanel
฿3,898
฿4,327 total
includes taxes & fees
7 Sept - 8 Sept
Best Western Kent Narrows Inn
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
An outdoor event area with round tables and a view of the water.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

9. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
฿5,459
฿6,059 total
includes taxes & fees
8 Sept - 9 Sept
Hyatt Place Kent Narrows & Marina
View all properties

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

10/10 Excellent
"The room was clean and the pool was well maintained. Breakfast and coffee were very good. Pleasant stay. Easy on and off I95."
Bettyann 1-night trip
Posted 19 hours ago
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Loved everything about this hotel."
Russell 2-night trip
Posted 20 hours ago
Pendry Baltimore
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 1 day ago
Annapolis Waterfront Hotel, Autograph Collection
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Our receptionist was very friendly and helpful. The room was clean and modern. Cooling system was good. Nice bathroom. The outdoor pool was clean and quiet and well maintained. Breakfast was standard travel fare but it was very fresh."
E Gaill 1-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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

8/10 Good
"Everything was good. I would suggest flipping around the mattress to prevent one side from losing shape making for an uncomfortable sleep. I did not want to alert the staff or complain. I just slept on the higher side of the bed. Other than that, our stay was nice."
Dawanda 2-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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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