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Search Family-Friendly Hotels in Chestertown

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Check availability on Chestertown Family-Friendly Hotels

Tonight
1 Nov - 2 Nov
Tomorrow
2 Nov - 3 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 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, (835)
"Very helpful front desk woman. On first perusal property appears a erase but clean, helpful, reasonable for a short stay. "
United States
Freda
The price is ฿3,298
฿3,660 total
includes taxes & fees
4 Nov - 5 Nov
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, (409)
"Food stains on the carpets, spots throughout the carpets in commons and in rooms."
United States
Allen
The price is ฿2,328
฿2,584 total
includes taxes & fees
30 Nov - 1 Dec
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, (299)
"Friendly staff, comfortable bed and clean room "
United States
DAVID
The price is ฿3,492
฿3,876 total
includes taxes & fees
16 Nov - 17 Nov
Fairfield Inn & Suites by Marriott 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, (913)
"Excellent, pet friendly, clean, convenient, and beautiful "
United States
John
The price is ฿2,554
฿2,835 total
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1011)
"It’s safe & comfortable to stay there"
United States
Jian
The price is ฿2,995
฿3,355 total
includes taxes & fees
23 Nov - 24 Nov
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Reception
Hampton Inn Middletown
Hampton Inn Middletown
2.5 star property
8.8 out of 10, Excellent, (849)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
The price is ฿3,396
฿3,770 total
includes taxes & fees
19 Nov - 20 Nov
Hampton Inn Middletown
Lobby
Quality Inn
Quality Inn
2.5 star property
7.8 out of 10, Good, (847)
"Great place and great staff"
United States
Rhonda
The price is ฿3,111
฿3,453 total
includes taxes & fees
6 Nov - 7 Nov
Quality Inn
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, (1003)
"Clean room and good location to biking trail."
United States
Cynthia
The price is ฿2,975
฿3,302 total
includes taxes & fees
16 Nov - 17 Nov
Best Western Kent Narrows Inn
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, (790)
"Friendly staff; great sized room & walk in shower. Great for traveling through stay! Thank you!"
United States
Nancy
The price is ฿2,721
฿3,047 total
includes taxes & fees
9 Nov - 10 Nov
Comfort Inn & Suites Aberdeen near 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.
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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"We went on a family weekend getaway. The hotel is a few minutes drive from the harbor. The pool was a favorite with the kids . We loved the fact the comedy club and safari night club was conveniently located on the property. The breakfast needed other meat options other than pork sausage, a beef or turkey bacon would’ve been better options . The hotel was clean , security was phenomenal especially during event times keeping hotel guest secure. I would definitely stay here again "
Jannelle 2-night trip
Posted 6 days ago
Best Western Plus Hotel & Conference Center
Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

10/10 Excellent
"Staff"
Wayne 1-night trip
Posted 10 days ago
Americas Best Value Inn Edgewood

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.