Family Hotels & Resorts in Chestertown from AU$119

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Check availability on Chestertown Family 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, (866 reviews)
"Everything was well!"
United States
Ahmed
The price is AU$166
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)
"Clean and friendly staff. Good location."
United States
Robert
The price is AU$119
includes taxes & fees
22 Jan - 23 Jan
Red Roof Inn & Suites Chestertown
Outdoor pool

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is AU$240
includes taxes & fees
19 Jan - 20 Jan
First Floor Studio Apartment in Historic 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, (333 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is AU$168
includes taxes & fees
25 Jan - 26 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, (1,002 reviews)
"Room was great and staff excellent. "
United States
Robert
The price is AU$142
includes taxes & fees
30 Jan - 31 Jan
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, (867 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is AU$147
includes taxes & fees
19 Jan - 20 Jan
Quality Inn Grasonville near Kent Island
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (870 reviews)
"Amazing stay"
United States
Katiana
The price is AU$158
includes taxes & fees
27 Jan - 28 Jan
Hampton Inn Middletown
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, (952 reviews)
"Great staff, clean room, nice view!"
United States
Quiana
The price is AU$157
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (829 reviews)
"I love this property very quiet and it's convenient to the shopping center and if you want other food it's connected to an IHOP you don't have to go out in the elements "
United States
Shelia
The price is AU$126
includes taxes & fees
30 Jan - 31 Jan
Comfort Inn & Suites Aberdeen near APG
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (701 reviews)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is AU$214
includes taxes & fees
19 Jan - 20 Jan
Hyatt Place Kent Narrows & Marina
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Clean room, staff was very friendly and kept in touch throughout stay, to see if I needed anything. Highly recommended staying here"
raymond 2-night trip
Posted 4 days ago
Historic Inns of Annapolis

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.