Chestertown Hotel Guide - Family Friendly Hotels in Chestertown, Maryland

  • 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

Our top choices for Chestertown family-friendly hotels

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 €91
includes taxes & fees
26 Jan - 27 Jan
Hampton Inn Middletown
Arcade

Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (432 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 €101
includes taxes & fees
17 Jan - 18 Jan
Holiday Inn Express Aberdeen by IHG
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (700 reviews)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is €123
includes taxes & fees
19 Jan - 20 Jan
Hyatt Place Kent Narrows & Marina
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (426 reviews)
"Clean and friendly staff. Good location."
United States
Robert
The price is €69
includes taxes & fees
21 Jan - 22 Jan
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, (866 reviews)
"Everything was well!"
United States
Ahmed
The price is €95
includes taxes & fees
1 Feb - 2 Feb
Comfort 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, (333 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is €96
includes taxes & fees
1 Feb - 2 Feb
Fairfield Inn & Suites by Marriott 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, (867 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is €84
includes taxes & fees
19 Jan - 20 Jan
Quality Inn Grasonville near Kent Island
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 €80
includes taxes & fees
22 Jan - 23 Jan
Best Western Kent Narrows Inn
Reception

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh
2.5 star property
Nottingham
8.6 out of 10, Excellent, (1,000 reviews)
"Great place to stay"
United States
brian
The price is €96
includes taxes & fees
19 Jan - 20 Jan
Fairfield Inn & Suites by Marriott White Marsh
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, (950 reviews)
"Great staff, clean room, nice view!"
United States
Quiana
The price is €91
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG
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

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 3 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 Crumpton Auction and Garfield Center for the Arts at the Prince Theater.