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

Chestertown Hotel Guide - Family Friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Family Friendly Hotels

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

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 room with two beds, a desk, a TV, and a window with curtains.
A modern lounge area with seating, a fireplace, and a television.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

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.
€103
includes taxes & fees
22 Sept - 23 Sept
Comfort Inn & Suites Chestertown
A hotel room with a bed, a desk, a chair, a sofa, and a painting on the wall.
A hotel room with a sofa, two beds, a desk, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
  • Cosy family retreat with free Wi-Fi, cots, and premium TV entertainment for memorable stays in the heart of Chestertown.
€67
includes taxes & fees
30 Aug - 31 Aug
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
  • Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
€60
includes taxes & fees
30 Aug - 31 Aug
Driftwood Inn
A pool area with a fence, trees, and a bench.
A house with a swimming pool, surrounded by a fence, and two red umbrellas.
A closet with a wooden floor, a white door, and a blue bag on top.
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
€140
includes taxes & fees
8 Sept - 9 Sept
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 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 swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

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.
€116
includes taxes & fees
1 Sept - 2 Sept
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 sofa, armchairs, a desk with a computer, a TV, and a plant.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
€96
includes taxes & fees
28 Sept - 29 Sept
Quality Inn Grasonville near Kent Island
A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A restaurant with a counter, seating area, and a clock on the wall.

7. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
€111
includes taxes & fees
28 Sept - 29 Sept
Best Western Kent Narrows Inn
A modern building with a patio area featuring outdoor seating and a fire pit.
A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.
A modern living room with a stone accent wall, a flat-screen TV, a dining area with a table and chairs, and a sofa with cushions.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.

8. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
€113
includes taxes & fees
6 Sept - 7 Sept
Fairfield Inn & Suites by Marriott Middletown
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.
An outdoor event area with round tables and a view of the water.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

9. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
€159
includes taxes & fees
8 Sept - 9 Sept
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.

10. 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.
€92
includes taxes & fees
11 Sept - 12 Sept
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Perfect for business and quick family stop travels. Staff is amazing and extremely generous. Clean and well stocked."
Kyle 1-night trip
Posted 1 day ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great view of the water."
LINDA 1-night trip
Posted 2 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

10/10 Excellent
"Breakfast was good."
Thomas 1-night trip
Posted 2 days ago
Hampton Inn Baltimore/White Marsh
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"The location of the hotel was awesome along with our balcony view. However you should not have to pay an additional $50 per day to park your car especially since the garage up the street is Therefore the guests are getting pentalized to park at the hotel . Additionally the front desk women were rude and condescending"
Michele 2-night trip
Posted 3 days ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

What's Chestertown like for family-friendly holidays?
If you've been thinking about a trip with your children, 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 holiday destination for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city centre.
What's the best family accommodation in 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 child-friendly holiday.
When's the best time to book a family-friendly holiday in Chestertown?
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's there to see and do with your family in Chestertown?
While you are holidaying in Chestertown, you and the family may want to see some interesting spots such as Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Make sure that you have lots of time for activities such as Rolphs Wharf Marina and Crumpton Auction.