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

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Check availability on Chestertown Family friendly Hotels

Our top choices for Chestertown family-friendly hotels

Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (933 reviews)
The price is S$143
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Grasonville near Kent Island
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,007 reviews)
The price is S$179
includes taxes & fees
15 Jul - 16 Jul
Best Western Kent Narrows Inn
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (931 reviews)
  • cleanliness
    Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.
The price is S$154
includes taxes & fees
6 Aug - 7 Aug
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (460 reviews)
  • cleanliness
    Cosy family retreat with free Wi-Fi, cots, and premium TV entertainment for memorable stays in the heart of Chestertown.
The price is S$103
includes taxes & fees
19 Jul - 20 Jul
Red Roof Inn & Suites Chestertown
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
The price is S$170
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
  • cleanliness
    Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
The price is S$91
includes taxes & fees
12 Jul - 13 Jul
Driftwood Inn
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (409 reviews)
The price is S$171
includes taxes & fees
12 Jul - 13 Jul
Fairfield Inn & Suites by Marriott Middletown
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,008 reviews)
  • cleanliness
    Splash into family fun at Aberdeen's seasonal outdoor pool where comfortable rooms await after sun-filled adventures in the park.
The price is S$164
includes taxes & fees
29 Jul - 30 Jul
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Fridge, microwave

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (509 reviews)
  • cleanliness
    Create a family paradise minutes from Sandy Point State Park where complimentary cots and premium TV channels await young travellers.
The price is S$122
includes taxes & fees
12 Jul - 13 Jul
Village Inn Annapolis MD
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,894 reviews)
  • cleanliness
    This family-friendly escape offers cots, premium TV channels, and a nature park just steps away from historic elegance.
The price is S$177
includes taxes & fees
20 Jul - 21 Jul
Historic Inns of Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at family-friendly hotels in Chestertown

Breakfast included
Pool

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Only thing was would not let delivery come to room when was ready for bed-- I don't understand why. Convenient for customers when relaxing in room"
Lisa 1-night trip
Posted 13 hours ago
Best Western Plus Hotel & Conference Center

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 Rolphs Wharf Marina and Historical Society of Kent County Maryland. Make sure that you have lots of time for activities such as Garfield Center for the Arts at the Prince Theater and Crumpton Auction.

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