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

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Check availability on Chestertown Family Hotels

Tonight
30 Sep - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chestertown family-friendly hotels

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A modern lounge area with seating, a fireplace, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
  • Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.
AED 381
AED 423 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn & Suites Chestertown
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 room with a bed, a sofa, a desk, 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.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
  • Cozy family retreat with free Wi-Fi, cribs, and premium TV entertainment for memorable stays in the heart of Chestertown.
AED 264
AED 294 total
includes taxes & fees
7 Oct - 8 Oct
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A living room with a wooden cabinet, a television, a sofa, and a dining table.
A two-story building with a brick facade, large windows, and a sloped roof.

3. Driftwood Inn

Driftwood Inn
Chestertown
  • Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
AED 233
AED 259 total
includes taxes & fees
1 Oct - 2 Oct
Driftwood Inn
A pool area with a fence, trees, and a bench.
A bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.
A house with a swimming pool, surrounded by a fence, and two red umbrellas.
A building with a balcony and large windows, surrounded by trees and a fence.

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
AED 364
AED 583 total
includes taxes & fees
1 Oct - 2 Oct
First Floor Studio Apartment in Historic Chestertown
Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
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
  • Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
AED 404
AED 448 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
A spacious lobby with a staircase, a reception desk, and a dining area.
A hotel room with a bed, a sofa, a desk, and two chairs. There are two lamps on the desk and a picture frame on the wall.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
AED 367
AED 408 total
includes taxes & fees
20 Oct - 21 Oct
Quality Inn Grasonville near Kent Island
A bathroom with a white toilet, a shower with a curtain, and a bathtub.
An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.
A reception desk with a clock, framed pictures, and a sign for express checkout.
Room

7. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
AED 467
AED 519 total
includes taxes & fees
7 Oct - 8 Oct
Best Western Kent Narrows Inn
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.

8. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
AED 558
AED 620 total
includes taxes & fees
13 Oct - 14 Oct
Hyatt Place Kent Narrows & Marina
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 hotel lobby with seating areas, a TV on the wall, and patterned curtains.
A hotel room with a bed, a desk with a chair, a television, and artwork on the wall.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
  • Splash into family fun at Aberdeen's seasonal outdoor pool where comfortable rooms await after sun-filled adventures in the park.
AED 367
AED 411 total
includes taxes & fees
1 Oct - 2 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A hotel lobby with a sofa, armchairs, a glass coffee table, and a dining area with chairs and tables.
A hotel room with a bed, a desk, a chair, a TV, and a lamp.
A hotel lobby with a bar area, a staircase, and a kitchen in the background.
A hotel room with a sofa, armchairs, a glass coffee table, a side table with a lamp, a mirror, and a view of the outside through a door.

10. Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood
Edgewood
AED 219
AED 245 total
includes taxes & fees
1 Oct - 2 Oct
Americas Best Value Inn Edgewood
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Choose what matters most at family-friendly hotels in Chestertown

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Excellent location. Marriott has renovated the bar downstairs; one side is a Mexican restaurant and the other is Italian. Both have great food and service."
Tammy 2-night trip
Posted 1 day ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

What's Chestertown like for family-friendly vacations?
If you've been thinking about a trip with your kids, the historic destination of Chestertown is a good choice. The boating, festivals, and sporting events are just a few things that make this an attractive vacation spot for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center.
What's the best place to stay when traveling with kids to Chestertown?
Comfort Inn & Suites Chestertown is a hotel with free parking and free full breakfast, and it's a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good option for your family trip.
When's the best time to book a family-friendly vacation in Chestertown?
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's there to see and do with your family in Chestertown?
While you are vacationing in Chestertown, you and the family might want to see interesting spots such as Historical Society of Kent County Maryland and Rolphs Wharf Marina. Make sure you have lots of time for activities like Chestertown Farmers Market and Garfield Center for the Arts at the Prince Theater.