Photo by Assya A

Search Family-Friendly Hotels in Chestertown

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Family-Friendly Hotels

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Top Chestertown Family-Friendly Hotels

Lobby
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (834)
"The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. "
United States
Charlie
The price is ₹8,961
₹9,947 total
includes taxes & fees
29 Oct - 30 Oct
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (406)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
United States
Cynthia
The price is ₹7,116
₹7,899 total
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn & Suites Chestertown
Lobby
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown
2.5 star property
9.2 out of 10, Wonderful, (297)
"One of the best hotels I have ever stayed "
United States
jean
The price is ₹9,488
₹10,532 total
includes taxes & fees
16 Nov - 17 Nov
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
9.0 out of 10, Wonderful, (1002)
"Loved our stay! Will visit again soon!!! "
United States
Meagan
The price is ₹7,766
₹8,698 total
includes taxes & fees
2 Nov - 3 Nov
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
9.2 out of 10, Wonderful, (907)
"Nice Holiday Inn Express with great water views."
United States
Michael
The price is ₹9,752
₹10,824 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
Reception
Hampton Inn Middletown
Hampton Inn Middletown
2.5 star property
8.8 out of 10, Excellent, (844)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
The price is ₹9,163
₹10,171 total
includes taxes & fees
19 Nov - 20 Nov
Hampton Inn Middletown
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG
Comfort Inn & Suites Aberdeen near APG
2.5 star property
7.8 out of 10, Good, (788)
"The front desk staff were friendly and welcoming!"
United States
Bonnie
The price is ₹7,766
₹8,698 total
includes taxes & fees
29 Oct - 30 Oct
Comfort Inn & Suites Aberdeen near APG
Indoor pool
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
2.5 star property
7.2 out of 10, Good, (1011)
"I found the staff to be very friendly, I believe that it is a family owned / operated establishment and while the inside of the hotel "
United States
Natasha
The price is ₹5,974
₹6,691 total
includes taxes & fees
27 Oct - 28 Oct
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Lobby
Quality Inn
Quality Inn
2.5 star property
7.8 out of 10, Good, (844)
"Great place and great staff"
United States
Rhonda
The price is ₹8,446
₹9,375 total
includes taxes & fees
16 Nov - 17 Nov
Quality 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.
View all properties

Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"On arrival we met Catalina on reception. An extremely pleasant and helpful girl. After that our stay was very comfortable."
Christopher 1-night trip
Posted 2 days ago
Hilton Garden Inn Baltimore/White Marsh

Explore a world of travel with Expedia

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?
Red Roof Inn & Suites Chestertown is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families. Comfort 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.