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Family Hotels & Resorts in Chestertown from AU$139

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Check availability on Chestertown Family Hotels

Best Chestertown Family 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 AU$174
includes taxes & fees
26 Oct - 27 Oct
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking
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 AU$139
includes taxes & fees
30 Oct - 31 Oct
Red Roof Inn & Suites Chestertown
Outdoor pool
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (105)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
The price is AU$248
includes taxes & fees
30 Oct - 31 Oct
First Floor Studio Apartment in Historic Chestertown
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, (1000)
"Loved our stay! Will visit again soon!!! "
United States
Meagan
The price is AU$153
includes taxes & fees
30 Oct - 31 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Lobby
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown
2.5 star property
9.2 out of 10, Wonderful, (296)
"One of the best hotels I have ever stayed "
United States
jean
The price is AU$185
includes taxes & fees
16 Nov - 17 Nov
Fairfield Inn & Suites by Marriott Middletown
Lobby
Quality Inn
Quality Inn
2.5 star property
7.8 out of 10, Good, (843)
"Great place and great staff"
United States
Rhonda
The price is AU$164
includes taxes & fees
16 Nov - 17 Nov
Quality Inn
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 AU$178
includes taxes & fees
19 Nov - 20 Nov
Hampton Inn Middletown
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, (906)
"Nice Holiday Inn Express with great water views."
United States
Michael
The price is AU$190
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (787)
"The front desk staff were friendly and welcoming!"
United States
Bonnie
The price is AU$153
includes taxes & fees
3 Nov - 4 Nov
Comfort Inn & Suites Aberdeen near APG
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very good, (1000)
"Clean room and good location to biking trail."
United States
Cynthia
The price is AU$157
includes taxes & fees
16 Nov - 17 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.
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Loved everything. Perfect location right on the main drag "
Timothy 1-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 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.