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

Chestertown Hotel Guide - Family Friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Family Friendly Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 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 brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.
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.
€97
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 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.

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.
€71
includes taxes & fees
21 Oct - 22 Oct
Red Roof Inn & Suites Chestertown
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 two patterned armchairs, a wooden coffee table, and a standing fan.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

3. Driftwood Inn

Driftwood Inn
Chestertown
  • Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
€63
includes taxes & fees
14 Oct - 15 Oct
Driftwood Inn
A pool area with a fence, trees, and a bench.
A closet with a wooden floor, a white door, and a blue bag on top.
A building with a balcony and large windows, surrounded by trees and a fence.
A bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.

4. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
€146
includes taxes & fees
20 Oct - 21 Oct
First Floor Studio Apartment in Historic Chestertown
A playground with a wooden climbing structure, a slide, and swings.
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.
A campfire in a stone fire pit by a lakeside at sunset.

5. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
€110
includes taxes & fees
14 Oct - 15 Oct
The Lodge at Great Oak Landing
A spacious living area with a dining table, sofa, and a kitchen in the background.
A modern kitchen with white cabinets, a central island, and pendant lighting.
A modern kitchen with a large island, white cabinetry, and a view of the city.
A laundry room with two front-loading washing machines, a drying rack, and a small cabinet above the machines.

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
€313
includes taxes & fees
26 Oct - 27 Oct
Newly restored apartment in the heart of Chestertown
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 sunflower field with a white barn and a large house in the background.

7. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
€159
includes taxes & fees
1 Nov - 2 Nov
Inn at Huntingfield Creek
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.
A living room with a glass-top coffee table, a blue sofa, a patterned armchair, and a television on a wooden stand.
A grassy outdoor seating area with Adirondack chairs and a small table, surrounded by trees.
A garden with a statue, various shrubs, and a flower bed.

8. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
€263
includes taxes & fees
14 Oct - 15 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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.

9. 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.
€109
includes taxes & fees
1 Nov - 2 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.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
An outdoor event area with round tables and a view of the water.

10. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
€151
includes taxes & fees
19 Oct - 20 Oct
Hyatt Place Kent Narrows & Marina
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Choose what matters most at family-friendly hotels in Chestertown

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chestertown Hotel Reviews

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
"Everything was great."
Sheena 4-night trip
Posted 13 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good
"Our stay was quite un eventful and very restful with the following exception; I had checked the wrong date on the arrival and called Expedia to correct it which they said they would do, then beyond that my brother in law passed away and we had to leave a day early, which the hotel was very understanding and only charged for the nights we stayed. BUT Expedia has not refunded any of the excessive charges for either of the two nights involved. They sent a letter saying the hotel would not accept refunding the two nights, which is completely not true as I have a copy of the bill from the hotel and it only covers the two nights we actually spent. At this time I can never trust Expedia again to book anything!"
Steve 3-night trip
Posted 14 hours ago
Country Inn & Suites by Radisson, Baltimore North, MD
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 23 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
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 2 days 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 2 days ago
Hampton Inn Baltimore/Glen Burnie
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

8/10 Good
"good"
Hidenori 2-night trip
Posted 3 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.