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Family Hotels & Resorts in Chestertown from NZ$116

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Check availability on Chestertown Family Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Best Chestertown Family Hotels

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, (903)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is NZ$242
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (289)
"Friendly staff, comfortable bed and clean room "
The price is NZ$192
includes taxes & fees
19 Oct - 20 Oct
Fairfield Inn & Suites by Marriott Middletown
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, (1002)
"Loved our stay! Will visit again soon!!! "
The price is NZ$171
includes taxes & fees
3 Nov - 4 Nov
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (399)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is NZ$154
includes taxes & fees
12 Oct - 13 Oct
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (825)
"Friendly staff, clean room, convenient location. "
The price is NZ$218
includes taxes & fees
3 Nov - 4 Nov
Comfort 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, (102)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is NZ$272
includes taxes & fees
7 Oct - 8 Oct
First Floor Studio Apartment in Historic Chestertown
Driftwood Inn
Front of property – evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
The price is NZ$121
includes taxes & fees
27 Oct - 28 Oct
Driftwood Inn
Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
7.8 out of 10, Good, (1005)
"Very nice staff"
The price is NZ$201
includes taxes & fees
6 Oct - 7 Oct
Hilton Garden Inn Baltimore/White Marsh
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (837)
"Enjoyed the amenities and great location for shops nearby "
The price is NZ$203
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn Middletown
Best Western Kent Narrows Inn
In-room safe, individually decorated, individually furnished, desk

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very good, (1003)
"Clean well appointed room. Very pet friendly with a reasonable pet fee of $30."
The price is NZ$240
includes taxes & fees
2 Nov - 3 Nov
Best Western Kent Narrows 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

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

10/10 Excellent
"Love this hotel! Absolutely beautiful - from the pool on the harbor, to the atrium, to the restaurant - it's truly outstanding. The staff is also incredibly accomodating. I forgot several articles of clothing and they mailed them to me immediately. I highly recommend the Sagamore Pendry!"
Christine 2-night trip
Posted 1 day ago
Sagamore Pendry Baltimore

Explore a world of travel with Expedia

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?
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.