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

Kid Friendly Hotels in Chestertown

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Check availability on Chestertown Family friendly Hotels

Tonight
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
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 brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel reception area with a reception desk, a seating area, and a hallway leading to other rooms.
A hotel room with a desk, two chairs, a flat-screen TV, and a painting on the wall.

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.
RM415
RM460 total
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A living room with a fireplace, a television, and a stone accent wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
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.
RM294
RM326 total
includes taxes & fees
11 Oct - 12 Oct
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 hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A two-story building with a brick facade, large windows, and a sloped roof.

3. Driftwood Inn

Driftwood Inn
Chestertown
  • Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
RM259
RM288 total
includes taxes & fees
5 Oct - 6 Oct
Driftwood Inn
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.

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
RM441
RM504 total
includes taxes & fees
7 Oct - 8 Oct
The Lodge at Great Oak Landing
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 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
RM655
RM727 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.
An outdoor event area with round tables and a view of the water.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

6. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
RM621
RM689 total
includes taxes & fees
13 Oct - 14 Oct
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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A modern food court with a central island, various food stations, and a yogurt display.

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.
RM421
RM467 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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 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
RM486
RM540 total
includes taxes & fees
25 Oct - 26 Oct
Fairfield Inn & Suites by Marriott Middletown
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.
A gym with treadmills, elliptical machines, and a weight machine.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.

9. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
RM364
RM408 total
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A spacious lobby with a staircase, a reception desk, and a dining area.
A hotel room with a bed, a sofa, a desk, and two chairs. There are two lamps on the desk and a picture frame on the wall.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

10. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
RM392
RM435 total
includes taxes & fees
1 Nov - 2 Nov
Quality Inn Grasonville near Kent Island
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Our room was a little dated and worn, but had all the amenities we care about - comfy bed, good shower, nice towels - and was clean and quiet. Affordable and convenient to highway and shopping, with friendly helpful staff."
Joyce 1-night trip
Posted 4 hours ago
Hilton Garden Inn Baltimore/White Marsh
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

8/10 Good
"Hotel was nice, pool was closed, the bathroom door didn't close properly and needs to be fixed. Staff was SUPER NICE and very helpful. Overall you pay for the location, which is very convenient."
Sean 1-night trip
Posted 11 hours ago
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Quality Inn & Suites Bel Air I-95 Exit 77A

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

8/10 Good
"The room itself was rather clean. The few members of staff I spoke to were helpful. The breakfast offered was okay, though when I went I believe the batter was out. No one's fault just poor planning on my part. Overall a good stay for the price."
Jessica 1-night trip
Posted 1 day ago
Quality Inn & Suites Bel Air I-95 Exit 77A
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"ok"
James 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Had a good time. Nice area"
Thomas E 3-night trip
Posted 3 days ago
Hilton Garden Inn Kent Island Marina

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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