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
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Chestertown pet-friendly hotels

A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel room with a bed, a sofa, a dining table, and a small round table.
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Roberta
AED 361
AED 401 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
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.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Kate
AED 264
AED 294 total
includes taxes & fees
29 Oct - 30 Oct
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 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
23 Oct - 24 Oct
Driftwood Inn
A kitchen with wooden cabinets, a central island with bar stools, stainless steel appliances, and a red patterned rug.
A wooden staircase leading to a second floor, a large wooden bookcase, and a patterned rug on the floor.
A covered patio with a table and chairs, a grill, and a decorative railing.
A living room with a ceiling fan, a brown leather sofa, a coffee table, two armchairs, a patterned rug, and a bookshelf.

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
26 Oct - 27 Oct
Wren Retweet- Country Estate in Center of C’Town
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 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.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Terry Kyungho
AED 364
AED 404 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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.

6. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Joseph
AED 547
AED 607 total
includes taxes & fees
18 Nov - 19 Nov
Hyatt Place Kent Narrows & 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 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
Mary
AED 642
AED 719 total
includes taxes & fees
26 Oct - 27 Oct
Vandiver Inn
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 pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

8. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
Thomas
AED 313
AED 351 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A patio with outdoor seating, overlooking a marina with boats.
An indoor swimming pool with clear views of boats and water.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
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
AED 478
AED 531 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Kent Island Marina
A kitchen with wooden cabinets, a dining table, and a refrigerator.
A piano in a room with wooden flooring and a chair with a floral pattern.
A two-story brick building with a front porch and a stack of bricks in the foreground.
A two-story brick building with a symmetrical facade, a central entrance, and a well-maintained lawn.

10. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
United States
Emily C.
Family Retreat at Lansdowne Manor
View all properties

Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Best in room dining"
Edgar 4-night trip
Posted 5 hours ago
Pendry Baltimore
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Great location, hotel super clean and good restaraunt . Short walking distance to great shopping and many more bars and restaraunts"
Robin 1-night trip
Posted 3 days ago
Annapolis Waterfront Hotel, Autograph Collection

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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