Family friendly Hotels in Chestertown, Maryland

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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, (861)
"Everything was well!"
United States
Ahmed
The price is P5,762
P6,396 total
includes taxes & fees
Jan 25 - Jan 26
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, (424)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is P4,237
P4,703 total
includes taxes & fees
Jan 7 - Jan 8
Red Roof Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is P3,737
P4,148 total
includes taxes & fees
Jan 30 - Jan 31
Driftwood Inn

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, (1003)
"Nice place"
United States
Maria
The price is P5,152
P5,770 total
includes taxes & fees
Jan 2 - Jan 3
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (326)
"Clean room, great staff, recommended. "
United States
Tom
The price is P6,356
P7,055 total
includes taxes & fees
Jan 11 - Jan 12
Fairfield Inn & Suites by Marriott 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 P4,952
P5,497 total
includes taxes & fees
Jan 2 - Jan 3
Quality Inn Grasonville near Kent Island

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (868)
"Amazing stay"
United States
Katiana
The price is P5,598
P6,213 total
includes taxes & fees
Jan 7 - Jan 8
Hampton Inn Middletown

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, (946)
"It was very comfortable and clean"
United States
Maria
The price is P5,120
P5,683 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1000)
"Nice place "
United States
Tucker T
The price is P4,403
P4,887 total
includes taxes & fees
Jan 7 - Jan 8
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.

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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