An aerial view of a town with a river, buildings, and surrounding greenery.

Chestertown Hotel Guide - Pet Friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Pet Friendly Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 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 brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
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.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
€97
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 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.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Kate
€71
includes taxes & fees
21 Oct - 22 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
€63
includes taxes & fees
14 Oct - 15 Oct
Driftwood Inn
A hallway with wooden flooring, a door on the right, and a window at the end.
A living room with a brown leather sofa, a round coffee table with candles, a patterned rug, and a painting of a landscape.
A two-story house with a covered patio and a lawn.
A wooden door, a rug, a cabinet, and a lamp.

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

Wren Retweet- Country Estate in Center of C’Town
Chestertown
United States
Mandy D.
€417
includes taxes & fees
28 Oct - 29 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 modern food court with a central island, various food stations, and a yogurt display.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A reception desk with a modern design, a digital display, and a check-in counter.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
€109
includes taxes & fees
1 Nov - 2 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.
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.
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
€151
includes taxes & fees
19 Oct - 20 Oct
Hyatt Place Kent Narrows & Marina
A hotel entrance with a clear sign reading "LA QUINTA".
A hotel lobby with seating areas, a TV on the wall, and patterned curtains.
A modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.
A hotel lobby with multiple dining tables and chairs, a reception area with a counter and a television, and large windows with red curtains.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
United States
robin
€108
includes taxes & fees
14 Oct - 15 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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.

8. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
Charles
€137
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Kent Island Marina
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 pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.
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
Regina
€85
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A hotel room with two beds, a desk, a chair, and a bathroom.
A poolside area with lounge chairs and a mural of a sunset over water.
A wooden pavilion with picnic tables and benches, a grill, and a red bench.
A snack and beverage section with shelves stocked with various snacks and a refrigerator with bottled drinks.

10. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Wesley
€89
includes taxes & fees
8 Nov - 9 Nov
Best Western Kent Narrows Inn
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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

10/10 Excellent
"Everything was great."
Sheena 4-night trip
Posted 13 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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.