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
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
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 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 spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
AED 358
AED 398 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 hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A multi-story brick building with a covered entrance and a parking lot.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Kate
AED 264
AED 294 total
includes taxes & fees
22 Oct - 23 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 hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
AED 233
AED 259 total
includes taxes & fees
17 Oct - 18 Oct
Driftwood Inn
A hallway with wooden flooring, a door on the right, and a window at the end.
A bedroom with a four-poster bed, wooden shelving with books and decorative items, and a fireplace.
A wooden door, a rug, a cabinet, and a lamp.
A living room with a brown leather sofa, a round coffee table with candles, a patterned rug, and a painting of a landscape.

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
27 Oct - 28 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
Marc
AED 364
AED 404 total
includes taxes & fees
15 Nov - 16 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.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
An outdoor event area with round tables and a view of the water.

6. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Joseph
AED 558
AED 620 total
includes taxes & fees
25 Oct - 26 Oct
Hyatt Place Kent Narrows & Marina
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.
A formal dining room with a long table, chairs, a chandelier, and a fireplace.
A cozy living room with a sofa, armchair, and a fireplace.
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 588
AED 659 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.
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 spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

9. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
Charles
AED 539
AED 598 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Kent Island Marina
A modern lobby with a curved sofa, red armchairs, a fireplace, and a dining area with green chairs.
A hotel room with a dining area, a TV, a dresser, and a tray table.
A hotel dining area with a buffet setup, multiple dining tables, chairs, and a ceiling fan.
An outdoor patio with round tables and chairs, a barbecue grill, and umbrellas providing shade.

10. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
United States
Jennifer
AED 372
AED 416 total
includes taxes & fees
1 Nov - 2 Nov
Homewood Suites by Hilton Bel Air
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Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Perfect place to stay! Classy. Clean comfortable amazing staff"
Nila 2-night trip
Posted 1 day ago
Annapolis Waterfront Hotel, Autograph Collection
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Great service teams and beautiful property! Also had a large group family style dinner in the Rec Pier Chop House and the food and service was superb! I’d definitely stay here again!"
Lori 2-night trip
Posted 2 days 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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