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
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for Chestertown pet-friendly hotels

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
Exterior
A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a concrete deck.
Exterior

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
AED 373
AED 414 total
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A multi-story brick building with a covered entrance and a parking lot.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
AED 264
AED 294 total
includes taxes & fees
11 Oct - 12 Oct
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A living room with a wooden cabinet, a television, a sofa, and a dining table.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A two-story building with a brick facade, large windows, and a sloped roof.

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
AED 233
AED 259 total
includes taxes & fees
4 Oct - 5 Oct
Driftwood Inn
A hallway with wooden flooring, a door on the right, and a window at the end.
A two-story house with a covered patio and a lawn.
A living room with a brown leather sofa, a round coffee table with candles, a patterned rug, and a painting of a landscape.
A bedroom with a four-poster bed, wooden shelving with books and decorative items, and a fireplace.

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

Wren Retweet- Country Estate in Center of C’Town
Chestertown
United States
Mandy D.
AED 1,119
AED 1,768 total
includes taxes & fees
6 Oct - 7 Oct
Wren Retweet- Country Estate in Center of C’Town
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
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.

5. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
AED 558
AED 620 total
includes taxes & fees
13 Oct - 14 Oct
Hyatt Place Kent Narrows & Marina
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 cozy living room with a sofa, armchair, and a fireplace.
A formal dining room with a long table, chairs, a chandelier, and a fireplace.

6. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
AED 642
AED 719 total
includes taxes & fees
13 Oct - 14 Oct
Vandiver Inn
A patio with outdoor seating, overlooking a marina with boats.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
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.

7. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
AED 509
AED 565 total
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Kent Island Marina
An outdoor patio with seating, a fire pit, and a barbecue area.
A modern indoor swimming pool with clear glass walls, a tiled floor, and a seating area with tables and chairs.
A multi-story hotel with a modern design, featuring a prominent entrance with a covered area and a sign that reads "Towneplace Suites by Marriott."
A compact kitchen with a refrigerator, microwave, and dishwasher. There is a dining area with a table and chairs, and a window with curtains.

8. TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
Aberdeen
United States
Jose
AED 485
AED 543 total
includes taxes & fees
1 Nov - 2 Nov
TownePlace Suites by Marriott Edgewood Aberdeen
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.
A wooden pavilion with picnic tables and benches, a grill, and a red bench.
A poolside area with lounge chairs and a mural of a sunset over water.
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

9. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Beth
AED 398
AED 442 total
includes taxes & fees
4 Oct - 5 Oct
Best Western Kent Narrows 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 reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

10. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
Lyn
AED 313
AED 351 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
View all properties

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"ok"
James 1-night trip
Posted 7 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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 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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