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Check availability on Chestertown Family-Friendly Hotels

Our top choices for Chestertown family-friendly hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (867 reviews)
"Everything was well!"
United States
Ahmed
The price is ฿3,141
฿3,487 total
includes taxes & fees
1 Feb - 2 Feb
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, (427 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is ฿2,234
฿2,480 total
includes taxes & fees
28 Jan - 29 Jan
Red Roof Inn & Suites Chestertown
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (336 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is ฿3,227
฿3,582 total
includes taxes & fees
28 Jan - 29 Jan
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, (1,005 reviews)
"Room was great and staff excellent. "
United States
Robert
The price is ฿2,584
฿2,895 total
includes taxes & fees
31 Jan - 1 Feb
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (868 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is ฿2,769
฿3,073 total
includes taxes & fees
27 Jan - 28 Jan
Quality Inn Grasonville near Kent Island
Arcade

Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (435 reviews)
"Claudia at the front desk was awesome!! Clean room amd great location. Only downside was the loud traffic you could hear from the road in the room."
United States
Steven
The price is ฿3,287
฿3,682 total
includes taxes & fees
24 Jan - 25 Jan
Holiday Inn Express Aberdeen by IHG
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (871 reviews)
"Amazing stay"
United States
Katiana
The price is ฿2,951
฿3,276 total
includes taxes & fees
28 Jan - 29 Jan
Hampton Inn Middletown
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
7.8 out of 10, Good, (832 reviews)
"Room was nice area was good"
United States
Armond
The price is ฿2,347
฿2,629 total
includes taxes & fees
30 Jan - 31 Jan
Comfort Inn & Suites Aberdeen near APG
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,001 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is ฿2,588
฿2,873 total
includes taxes & fees
28 Jan - 29 Jan
Best Western Kent Narrows Inn
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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Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Clean rooms"
Ji 1-night trip
Posted 10 days ago
Hampton Inn Baltimore/Glen Burnie

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