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Check availability on Chestertown Family-Friendly Hotels

Our top choices for Chestertown family-friendly hotels

Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (434 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 ฿2,278
฿2,528 total
includes taxes & fees
19 Apr - 20 Apr
Red Roof Inn & Suites Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (896 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 ฿3,691
฿4,097 total
includes taxes & fees
26 Apr - 27 Apr
Comfort Inn & Suites Chestertown
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,005 reviews)
The price is ฿3,182
฿3,532 total
includes taxes & fees
20 Apr - 21 Apr
Best Western Kent Narrows Inn
Room, Multiple Beds, Hot Tub (LC) | Interior

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
The price is ฿13,185
฿15,674 total
includes taxes & fees
14 Apr - 15 Apr
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (888 reviews)
The price is ฿3,131
฿3,475 total
includes taxes & fees
15 Apr - 16 Apr
Quality Inn Grasonville near Kent Island
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, (369 reviews)
The price is ฿3,332
฿3,698 total
includes taxes & fees
26 Apr - 27 Apr
Fairfield Inn & Suites by Marriott Middletown
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

6/10 Okay
"just a little concern about the pillows smells bad and i can't sleep for the whole night"
Jaycee 1-night trip
Posted 1 hour ago
Hampton Inn & Suites Edgewood/Aberdeen-South

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