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
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Chestertown pet-friendly hotels

A hotel lobby with a fireplace, seating area, and a television.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A hotel room with a bed, a sofa, a dining table, and a small round table.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Michael
₹9,327
₹10,353 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
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.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.

2. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
₹6,029
₹6,693 total
includes taxes & fees
27 Oct - 28 Oct
Driftwood Inn
A living room with a fireplace, a television, and a stone accent wall.
A hotel room with a sofa, two beds, a painting, and a lamp.
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.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Mary
₹6,835
₹7,587 total
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn & Suites Chestertown
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 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.

4. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Joseph
₹14,431
₹16,019 total
includes taxes & fees
2 Nov - 3 Nov
Hyatt Place Kent Narrows & Marina
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 buffet with various food items, including omelets and baked goods, served in metal containers.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Michelle
₹9,969
₹11,066 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.
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.

6. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
Thomas
₹8,097
₹9,068 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A modern building with a patio area featuring outdoor seating and a fire pit.
A Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.
A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

7. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
United States
Sharon
₹11,298
₹12,541 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Middletown
A hotel room with a large bed, a sofa, a TV, and a wall-mounted artwork.
An outdoor patio area with a sectional sofa, lounge chairs, and a round table.
A pool area with chairs and a changing room.
A modern hotel with a blue and white facade, a covered entrance, and a parking lot.

8. SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
Bel Air
United States
Nita
₹10,596
₹11,867 total
includes taxes & fees
4 Nov - 5 Nov
SpringHill Suites by Marriott Edgewood/Aberdeen
A patio with outdoor seating, overlooking a marina with boats.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
An indoor swimming pool with clear views of boats and water.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

9. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
Charles
₹12,440
₹13,809 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Kent Island Marina
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.
A traditional house with a covered porch, white picket fence, and lush greenery.
A cozy living room with a sofa, armchair, and a fireplace.
A bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.

10. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
₹16,596
₹18,587 total
includes taxes & fees
2 Nov - 3 Nov
Vandiver Inn
View all properties

Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Beautiful hotel and an incredible location"
Tanner 2-night trip
Posted 17 hours ago
Pendry Baltimore
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Good hotel"
Michael 1-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Easy access to downtown, Great waterside restaurants."
John 1-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 Historical Society of Kent County Maryland and Chestertown Historic District. While you're there, make sure you don't miss Rolphs Wharf Marina and Northern Chesapeake Bay.

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