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

Find Kid Friendly Hotels in Chestertown from S$90

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Check availability on Chestertown Family friendly Hotels

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

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.
S$139
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 multi-story brick building with a covered entrance and a parking lot.
A hotel room with a bed, two bedside lamps, a sofa, a small table, 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
  • Cosy family retreat with free Wi-Fi, cots, and premium TV entertainment for memorable stays in the heart of Chestertown.
S$102
includes taxes & fees
20 Oct - 21 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
S$158
includes taxes & fees
20 Oct - 21 Oct
The Lodge at Great Oak Landing
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 living room with a wooden cabinet, a television, a sofa, and a dining table.
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.
S$90
includes taxes & fees
16 Oct - 17 Oct
Driftwood Inn
A poolside area with lounge chairs, a white picket fence, and a stack of towels.
A boat deck with a white bench and a view of a calm lake and distant trees.
A buffet with various food items including fruits, pastries, and salads.
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.

5. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
S$228
includes taxes & fees
1 Nov - 2 Nov
Inn at Huntingfield Creek
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.

6. 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 escapeโ€”enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
S$141
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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.
Marina
An outdoor event area with round tables and a view of the water.

7. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
S$216
includes taxes & fees
18 Oct - 19 Oct
Hyatt Place Kent Narrows & Marina
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 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
S$158
includes taxes & fees
18 Oct - 19 Oct
SpringHill Suites Baltimore White Marsh/Middle River
A patio with outdoor seating, overlooking a marina with boats.
A balcony with a view of a marina and row houses.
A balcony with a view of a body of water, a row of buildings, and a chair.
An indoor swimming pool with clear views of boats and water.

9. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
S$197
includes taxes & fees
20 Oct - 21 Oct
Hilton Garden Inn Kent Island Marina
A modern building with a patio area featuring outdoor seating and a fire pit.
A modern restaurant with a long counter, multiple seating areas, and pendant lighting.
A Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.
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
S$144
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

8/10 Good
"Loved the jacuzzi and the pool. Breakfast was great. & the club , club Safari is right next to the hotel and was great because I didnโ€™t have to go far for a night out. The DJ was awesome. Loved seeing the hotel cat around in the lobby :) . Staff were polite and helpful. Overall I really enjoyed my stay and will book here again with no problem!"
Ashley 2-night trip
Posted 7 hours ago
Best Western Plus Hotel & Conference Center
Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Nice"
James 1-night trip
Posted 16 hours ago
Historic Inns of Annapolis
Quality Inn & Suites Bel Air I-95 Exit 77A

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

8/10 Good
"Everything was good. For breakfast only waffle and cornflakes were available."
Vinoth 1-night trip
Posted 4 days ago
Quality Inn & Suites Bel Air I-95 Exit 77A

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 23ยฐC, while the coldest months are January and February, with an average of 4ยฐC. 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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