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

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Check availability on Chestertown Family-Friendly Hotels

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Chestertown family-friendly hotels

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
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
  • Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.
฿3,275
฿3,635 total
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 hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A multi-story brick building with a covered entrance and a parking lot.

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.
฿2,414
฿2,679 total
includes taxes & fees
19 Oct - 20 Oct
Red Roof Inn & Suites Chestertown
A playground with a wooden climbing structure, a slide, and swings.
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
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.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
฿3,621
฿4,140 total
includes taxes & fees
14 Oct - 15 Oct
The Lodge at Great Oak Landing
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 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.

4. Driftwood Inn

Driftwood Inn
Chestertown
  • Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
฿2,129
฿2,364 total
includes taxes & fees
13 Oct - 14 Oct
Driftwood Inn
A poolside area with lounge chairs, a white picket fence, and a stack of towels.
A sunflower field with a white barn and a large house in the background.
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.
A buffet with various food items including fruits, pastries, and salads.

5. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
฿5,374
฿5,965 total
includes taxes & fees
1 Nov - 2 Nov
Inn at Huntingfield Creek
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
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.

6. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
฿5,097
฿5,657 total
includes taxes & fees
18 Oct - 19 Oct
Hyatt Place Kent Narrows & Marina
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.

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.
฿3,521
฿3,908 total
includes taxes & fees
8 Nov - 9 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 modern bathroom with a large mirror, two sinks, and a glass-enclosed shower.
An outdoor patio with brick walls, green chairs, and a fire pit.
A hotel with a modern facade, a covered entrance, and a red car parked outside.

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
฿3,591
฿4,148 total
includes taxes & fees
18 Oct - 19 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 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
฿2,859
฿3,203 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A modern building with a patio area featuring outdoor seating and a fire pit.
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 living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.

10. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
฿3,990
฿4,429 total
includes taxes & fees
25 Oct - 26 Oct
Fairfield Inn & Suites by Marriott Middletown
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"The rooms were clean and nicely remodeled. There was a continental breakfast and Dennys across the way. Staff was kind and a place On comfort"
Angelique 1-night trip
Posted 2 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Nice breakfast very pet safe and friendly, Big mini fridge and comfy bed 2 chairs and a bench."
Regina 1-night trip
Posted 6 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
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
"Little weird driveway"
Anto 1-night trip
Posted 19 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"This is like our home away from home when visiting our son at college."
Kwame 2-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott White Marsh
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

8/10 Good
"A good location. Many stores and restaurants within walking distance and many more a short drive away."
Justin 2-night trip
Posted 1 day ago
Hampton Inn Baltimore/Glen Burnie
Pendry Baltimore

Pendry Baltimore

8/10 Good
"Beautiful Room"
Paul 2-night trip
Posted 2 days ago
Pendry Baltimore
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

8/10 Good
"good"
Hidenori 2-night trip
Posted 2 days ago
Hampton Inn Baltimore/White Marsh

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.

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