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

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Check availability on Chestertown Family 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 modern bathroom with a white sink, mirror, and toilet. There is a hand dryer and a towel rack.
A hotel room with two beds, a desk, a flat-screen TV, 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.
AED 359
AED 398 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 multi-story brick building with a covered entrance and a parking lot.
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.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
  • Cozy family retreat with free Wi-Fi, cribs, and premium TV entertainment for memorable stays in the heart of Chestertown.
AED 264
AED 294 total
includes taxes & fees
19 Oct - 20 Oct
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
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.

3. Driftwood Inn

Driftwood Inn
Chestertown
  • Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
AED 233
AED 259 total
includes taxes & fees
14 Oct - 15 Oct
Driftwood Inn
A playground with a wooden climbing structure, a slide, and swings.
A campfire in a stone fire pit by a lakeside at sunset.
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
AED 397
AED 454 total
includes taxes & fees
15 Oct - 16 Oct
The Lodge at Great Oak Landing
A pool area with a fence, trees, and a bench.
A bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.
A house with a swimming pool, surrounded by a fence, and two red umbrellas.
A closet with a wooden floor, a white door, and a blue bag on top.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
AED 364
AED 583 total
includes taxes & fees
19 Oct - 20 Oct
First Floor Studio Apartment in Historic Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.
A laundry room with two front-loading washing machines, a drying rack, and a small cabinet above the machines.
A bedroom with a large bed, a nightstand, a lamp, a patterned rug, and a view through an open door to a hallway.
A modern kitchen with a large island, white cabinetry, and a view of the city.

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
AED 826
AED 1,293 total
includes taxes & fees
18 Oct - 19 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 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.

7. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
AED 589
AED 653 total
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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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 modern food court with a central island, various food stations, and a yogurt display.

8. 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.
AED 404
AED 448 total
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.

9. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
AED 558
AED 620 total
includes taxes & fees
20 Oct - 21 Oct
Hyatt Place Kent Narrows & Marina
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.
A grassy outdoor seating area with Adirondack chairs and a small table, surrounded by trees.
A living room with a glass-top coffee table, a blue sofa, a patterned armchair, and a television on a wooden stand.
A marina with boats docked, a building with a white facade, and a restaurant with outdoor seating.

10. 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
AED 433
AED 1,042 total
includes taxes & fees
14 Oct - 15 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"We stayed here overnight so that we didn't have to travel from MoCo to Annapolis for an early morning conference. We stayed in the Maryland Inn, it was quaint, very clean, and cute. We really enjoyed the property, its location to the water and the conference. We'd definitely stay here again."
Yvette 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"all good. Very good when it comes to parking during a boat show."
George 3-night trip
Posted 4 hours ago
Annapolis Waterfront Hotel, Autograph Collection
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 20 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 21 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 1 day 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 vacations?
If you've been thinking about a trip with your kids, 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 vacation spot for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center.
What's the best place to stay when traveling with kids to 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 family trip.
When's the best time to book a family-friendly vacation in Chestertown?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What's there to see and do with your family in Chestertown?
While you are vacationing in Chestertown, you and the family might want to see interesting spots such as Historical Society of Kent County Maryland and Rolphs Wharf Marina. Make sure you have lots of time for activities like Chestertown Farmers Market and Garfield Center for the Arts at the Prince Theater.