Find Family Hotels in Chestertown, MD

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Our top choices for Chestertown family-friendly hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (863)
"Everything was well!"
United States
Ahmed
The price is NT$2,994
NT$3,324 total
includes taxes & fees
Jan 26 - Jan 27
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (426)
"Clean and friendly staff. Good location."
United States
Robert
The price is NT$2,262
NT$2,510 total
includes taxes & fees
Jan 16 - Jan 17
Red Roof Inn & Suites Chestertown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (331)
"Clean room, great staff, recommended. "
United States
Tom
The price is NT$3,392
NT$3,765 total
includes taxes & fees
Jan 11 - Jan 12
Fairfield Inn & Suites by Marriott Middletown

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1005)
"Room was great and staff excellent. "
United States
Robert
The price is NT$2,697
NT$3,020 total
includes taxes & fees
Jan 10 - Jan 11
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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, (947)
"It was very comfortable and clean"
United States
Maria
The price is NT$2,733
NT$3,033 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Express Annapolis East-Kent Island by IHG

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (870)
"Amazing stay"
United States
Katiana
The price is NT$2,988
NT$3,316 total
includes taxes & fees
Jan 12 - Jan 13
Hampton Inn Middletown

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is NT$2,643
NT$2,934 total
includes taxes & fees
Jan 19 - Jan 20
Quality Inn Grasonville near Kent Island

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1004)
"Nice place "
United States
Tucker T
The price is NT$2,620
NT$2,908 total
includes taxes & fees
Jan 13 - Jan 14
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (694)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is NT$3,644
NT$4,044 total
includes taxes & fees
Jan 19 - Jan 20
Hyatt Place Kent Narrows & Marina
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.

Top Chestertown Hotel Reviews

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

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