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 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Chestertown pet-friendly hotels

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.
A hotel room with a bed, a desk with a coffee maker, a TV, a chair, 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
AED 360
AED 399 total
includes taxes & fees
8 Nov - 9 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 living room with a fireplace, a television, and a stone accent wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Kate
AED 264
AED 294 total
includes taxes & fees
18 Oct - 19 Oct
Red Roof 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 two patterned armchairs, a wooden coffee table, and a standing fan.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
AED 233
AED 259 total
includes taxes & fees
12 Oct - 13 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 1,135
AED 1,788 total
includes taxes & fees
3 Nov - 4 Nov
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
18 Oct - 19 Oct
Hyatt Place Kent Narrows & Marina
Two Adirondack chairs facing a calm body of water with a clear sky above.
A reception desk with a modern design, a digital display, and a check-in counter.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A modern food court with a central island, various food stations, and a yogurt display.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
AED 364
AED 404 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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 bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.
A traditional house with a covered porch, white picket fence, and lush greenery.

7. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
AED 642
AED 719 total
includes taxes & fees
12 Oct - 13 Oct
Vandiver Inn
A hotel entrance with a clear sign reading "LA QUINTA".
A hotel lobby with multiple dining tables and chairs, a reception area with a counter and a television, and large windows with red curtains.
A modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.
A vending area with two beverage dispensers, a wall-mounted display of personal care items, and shelves stocked with snacks and beverages.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
United States
robin
AED 393
AED 441 total
includes taxes & fees
12 Oct - 13 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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 room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.

9. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
Lyn
AED 313
AED 351 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A patio with outdoor seating, overlooking a marina with boats.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.
An indoor swimming pool with clear views of boats and water.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

10. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
Charles
AED 509
AED 565 total
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Kent Island Marina
View all properties

Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

8/10 Good
"Beautiful Room"
Paul 2-night trip
Posted 16 hours ago
Pendry Baltimore

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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