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

Find Pet-friendly Hotels in Chestertown, MD

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Check availability on Chestertown Pet-friendly Hotels

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Chestertown pet-friendly hotels

A hotel lobby with a fireplace, seating area, and a television.
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A hotel reception area with a reception desk, a seating area, and a hallway leading to other rooms.
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
Roberta
AED 360
AED 400 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
A living room with a fireplace, a television, and a stone accent wall.
A multi-story brick building with a covered entrance and a parking lot.
A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.
A hotel room with a bed, a desk, a chair, a sofa, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Mary
AED 264
AED 294 total
includes taxes & fees
1 Nov - 2 Nov
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 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
26 Oct - 27 Oct
Driftwood Inn
A covered porch with a wooden bench, potted plants, and a decorative railing.
A bedroom with a large bed, wooden bookshelves, a tall black column, and large windows.
A living room with a ceiling fan, a brown leather sofa, a coffee table, two armchairs, a patterned rug, and a bookshelf.
A living room with a dining area, a television, and a patterned rug.

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 1,261
AED 1,937 total
includes taxes & fees
8 Nov - 9 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
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
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
Joseph
AED 558
AED 620 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Kent Narrows & Marina
A gazebo with a view of a lake at dusk.
A buffet with various food items, including omelets and baked goods, served in metal containers.
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.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Michelle
AED 364
AED 404 total
includes taxes & fees
22 Nov - 23 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 formal dining room with a long table, chairs, a chandelier, and a fireplace.
A traditional house with a covered porch, white picket fence, and lush greenery.
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 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.

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 balcony with a view of a body of water, a row of buildings, and a chair.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
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 475
AED 527 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 two-story brick building with a front porch and a stack of bricks in the foreground.
A cozy dining room with a wooden table and chairs, surrounded by bookshelves and a fireplace.
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

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
"For a short stay, it was fine. Room was clean, however I noticed not cleaned when we left in the afternoon. Breakfast is not the best, but for something quick it works. La Quinta is not the same as it used to be, but if all you need is a good clean room and a bed for a couple nights, its fine. The mattress is horrible! I woke up with the worst pain in my hip."
cadian 2-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Great stay"
Mitchell 1-night trip
Posted 18 hours ago
Pendry Baltimore
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Easy access to downtown, Great waterside restaurants."
John 1-night trip
Posted 2 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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