Photo by Assya A

Find Family Hotels in Chestertown, MD

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Family Hotels

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Top Chestertown Family Hotels

Our top choices for Chestertown family-friendly hotels

Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (283)
"Friendly staff, comfortable bed and clean room "
The price is ￥15,351
￥17,040 total
includes taxes & fees
Oct 19 - Oct 20
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express White Marsh by IHG
Free continental breakfast

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (935)
"Very clean, friendly, great breakfast!"
The price is ￥14,761
￥17,049 total
includes taxes & fees
Oct 5 - Oct 6
Holiday Inn Express White Marsh by IHG
The Lodge at Great Oak Landing
Children's play area - outdoor

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (68)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is ￥19,529
￥21,678 total
includes taxes & fees
Sep 25 - Sep 26
The Lodge at Great Oak Landing
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (902)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is ￥19,927
￥22,118 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Annapolis East-Kent Island by IHG
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (820)
"Friendly staff, clean room, convenient location. "
The price is ￥16,529
￥18,348 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (396)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is ￥11,299
￥12,542 total
includes taxes & fees
Sep 30 - Oct 1
Red Roof Inn & Suites Chestertown
First Floor Studio Apartment in Historic Chestertown
Outdoor pool

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (100)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is ￥13,019
￥21,676 total
includes taxes & fees
Sep 25 - Sep 26
First Floor Studio Apartment in Historic Chestertown
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (834)
"Decent for a Hampton Inn"
The price is ￥16,196
￥17,977 total
includes taxes & fees
Sep 30 - Oct 1
Hampton Inn Middletown
Quality Inn
Lobby

Quality Inn

2.5 star property
7.8 out of 10, Good, (831)
"Great place and great staff"
The price is ￥15,684
￥17,411 total
includes taxes & fees
Sep 29 - Sep 30
Quality Inn
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.0 out of 10, Wonderful, (1013)
"Loved our stay! Will visit again soon!!! "
The price is ￥13,174
￥14,756 total
includes taxes & fees
Oct 5 - Oct 6
La Quinta Inn & Suites by Wyndham Aberdeen-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.
View all properties

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Stayed for one night; room was nice, easy to access, and located near numerous local attractions. "
Clifton 1-night trip
Posted 6 days ago
Historic Inns of Annapolis

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's Chestertown like for family-friendly vacations?
If you've been thinking about a trip with your kids, 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 vacation spot for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center.
What's the best place to stay when traveling with kids to 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 family trip.
When's the best time to book a family-friendly vacation in Chestertown?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What's there to see and do with your family in Chestertown?
While you are vacationing in Chestertown, you and the family might want to see interesting spots such as Historical Society of Kent County Maryland and Rolphs Wharf Marina. Make sure you have lots of time for activities like Garfield Center for the Arts at the Prince Theater and Crumpton Auction.