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
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Chestertown family-friendly hotels

A hotel lobby with a fireplace, seating area, and a television.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel reception area with a reception desk, a seating area, and a hallway leading to other rooms.
A hotel room with a bed, a sofa, a dining table, and a small round table.

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.
₹9,327
₹10,353 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
A playground with a wooden climbing structure, a slide, and swings.
A marina with boats docked, a sandy beach with umbrellas, and a pier extending into the water.
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A campfire in a stone fire pit by a lakeside at sunset.

2. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
₹10,254
₹11,723 total
includes taxes & fees
27 Oct - 28 Oct
The Lodge at Great Oak Landing
A living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, a desk, a chair, a sofa, and a painting on the 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.

3. 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.
₹6,835
₹7,587 total
includes taxes & fees
2 Nov - 3 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 two-story building with a brick facade, large windows, and a sloped roof.
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.
₹6,029
₹6,693 total
includes taxes & fees
27 Oct - 28 Oct
Driftwood Inn
A poolside area with lounge chairs, a white picket fence, and a stack of towels.
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 sunflower field with a white barn and a large house 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
₹13,302
₹14,766 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.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
Marina
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
₹14,431
₹16,019 total
includes taxes & fees
2 Nov - 3 Nov
Hyatt Place Kent Narrows & Marina
Two Adirondack chairs facing a calm body of water with a clear sky above.
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 reception desk with a modern design, a digital display, and a check-in counter.
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.
₹9,969
₹11,066 total
includes taxes & fees
15 Nov - 16 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 with a modern facade, a covered entrance, and a red car parked outside.
A modern bathroom with a large mirror, two sinks, and a glass-enclosed shower.
A hotel room with two beds, a bathroom, and a seating area.

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
₹10,168
₹11,744 total
includes taxes & fees
1 Nov - 2 Nov
SpringHill Suites Baltimore White Marsh/Middle River
A modern hotel lobby with a long dining table, several chairs, and a bar area.
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.
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
₹8,097
₹9,068 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 Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.
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.

10. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
₹11,298
₹12,541 total
includes taxes & fees
1 Nov - 2 Nov
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

8/10 Good
"Great property! The breakfast menu needs to be improved."
Gally 2-night trip
Posted 2 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Beautiful hotel and an incredible location"
Tanner 2-night trip
Posted 19 hours ago
Pendry Baltimore
Quality Inn & Suites Bel Air I-95 Exit 77A

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

8/10 Good
"Nice place for the weekend. They had good breakfast"
Jovan 2-night trip
Posted 20 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Good hotel"
Michael 1-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown
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 3 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 5 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.

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