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Check availability on Chestertown Family-Friendly Hotels

Tonight
24 Jan - 25 Jan
Tomorrow
25 Jan - 26 Jan
Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb

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, (869 reviews)
"staff is nice and place is good. proce wise is excellent"
United States
Janelle
The price is ₹9,493
₹10,537 total
includes taxes & fees
13 Feb - 14 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 ₹6,597
₹7,323 total
includes taxes & fees
3 Feb - 4 Feb
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, (338 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is ₹9,564
₹10,616 total
includes taxes & fees
29 Jan - 30 Jan
Fairfield Inn & Suites by Marriott 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, (955 reviews)
"Lovely location"
United States
Cheryl
The price is ₹8,000
₹8,880 total
includes taxes & fees
18 Feb - 19 Feb
Holiday Inn Express Annapolis East-Kent Island by IHG
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 ₹7,738
₹8,667 total
includes taxes & fees
30 Jan - 31 Jan
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (872 reviews)
"Amazing stay"
United States
Katiana
The price is ₹8,715
₹9,674 total
includes taxes & fees
24 Feb - 25 Feb
Hampton Inn Middletown
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 ₹8,206
₹9,109 total
includes taxes & fees
25 Jan - 26 Jan
Quality Inn Grasonville near Kent Island
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, (834 reviews)
"Room was nice area was good"
United States
Armond
The price is ₹6,957
₹7,791 total
includes taxes & fees
30 Jan - 31 Jan
Comfort Inn & Suites Aberdeen near APG
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
"YES"
Jerry 3-night trip
Posted 5 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 Rolphs Wharf Marina. Make sure that you have lots of time for activities such as Garfield Center for the Arts at the Prince Theater and Crumpton Auction.