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

Search Family-Friendly Hotels in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Family-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 family-friendly hotels

A hotel lobby with a fireplace, seating area, and a television.
A hotel room with a bed, a sofa, a dining table, and a small round 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.

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.
฿3,317
฿3,682 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.
A living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, a couch, a painting, and a window with curtains.
A hotel entrance with a clear sky, a parking lot, and a brick building with a covered entrance.

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.
฿2,431
฿2,698 total
includes taxes & fees
1 Nov - 2 Nov
Red Roof Inn & Suites Chestertown
A playground with a wooden climbing structure, a slide, and swings.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
฿3,647
฿4,169 total
includes taxes & fees
27 Oct - 28 Oct
The Lodge at Great Oak Landing
A row of motel rooms with stone walls and red doors.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.
A two-story building with a brick facade, large windows, and a sloped roof.
A living room with a wooden cabinet, a television, a sofa, and a dining table.

4. Driftwood Inn

Driftwood Inn
Chestertown
  • Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
฿2,144
฿2,380 total
includes taxes & fees
26 Oct - 27 Oct
Driftwood Inn
A poolside area with lounge chairs, a white picket fence, and a stack of towels.
A buffet with various food items including fruits, pastries, and salads.
A sunflower field with a white barn and a large house in the background.
A boat deck with a white bench and a view of a calm lake and distant trees.

5. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
฿4,731
฿5,251 total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
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.

6. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
฿5,132
฿5,697 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Kent Narrows & Marina
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 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.

7. 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.
฿3,343
฿3,710 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.
A hotel room with two beds, a bathroom, and a seating area.
A hotel with a modern facade, a covered entrance, and a red car parked outside.
An outdoor patio with brick walls, green chairs, and a fire pit.

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
฿3,616
฿4,177 total
includes taxes & fees
29 Oct - 30 Oct
SpringHill Suites Baltimore White Marsh/Middle River
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

9. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
฿2,879
฿3,225 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.
A spacious lobby with a beige sofa, blue armchairs, and a wooden coffee table. There are two floor lamps and a small round table.
A modern building with a stone facade, large windows, and outdoor seating area with chairs.

10. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
฿3,559
฿3,986 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Bel Air
View all properties

Choose what matters most at family-friendly hotels in Chestertown

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Good hotel"
Michael 1-night trip
Posted 9 hours ago
Comfort Inn & Suites Chestertown
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Great stay"
Mitchell 1-night trip
Posted 9 hours ago
Pendry Baltimore
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Everyone seemed to care and were nice"
james 1-night trip
Posted 2 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South
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
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Great stay!"
Dianne 2-night trip
Posted 3 days ago
Hampton Inn Baltimore/Glen Burnie

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 Rolphs Wharf Marina. Make sure that you have lots of time for activities such as Chestertown Farmers Market and Garfield Center for the Arts at the Prince Theater.

Explore a world of travel with Expedia