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Check availability on Chestertown Family Hotels

Tonight
Feb 2 - Feb 3
Tomorrow
Feb 3 - Feb 4
This weekend
Feb 6 - Feb 8
Next weekend
Feb 13 - Feb 15

Our top choices for Chestertown family-friendly hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (870 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is ₩146,117
₩162,190 total
includes taxes & fees
Mar 1 - Mar 2
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (427 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is ₩104,009
₩115,450 total
includes taxes & fees
Feb 8 - Feb 9
Red Roof Inn & Suites Chestertown
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (342 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is ₩139,978
₩155,375 total
includes taxes & fees
Feb 8 - Feb 9
Fairfield Inn & Suites by Marriott Middletown
Exterior

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, (1,002 reviews)
"Room was great and staff excellent. "
United States
Robert
The price is ₩125,243
₩140,271 total
includes taxes & fees
Feb 7 - Feb 8
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior

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, (956 reviews)
"Lovely location"
United States
Cheryl
The price is ₩150,234
₩166,760 total
includes taxes & fees
Mar 2 - Mar 3
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (874 reviews)
"Amazing stay"
United States
Katiana
The price is ₩137,407
₩152,522 total
includes taxes & fees
Feb 10 - Feb 11
Hampton Inn Middletown
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (869 reviews)
"Nice staff and rooms"
United States
Walter
The price is ₩122,788
₩136,295 total
includes taxes & fees
Mar 2 - Mar 3
Quality Inn Grasonville near Kent Island
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,000 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is ₩120,505
₩133,761 total
includes taxes & fees
Feb 8 - Feb 9
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

Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent
"The room layout was very good. Like it was done by someone who actually traveled a lot. Nice small kitchen. Lots of counter space. Several hooks in bathroom. Counter space in bathroom. "
Michael 2-night trip
Posted 20 hours ago
Home2 Suites by Hilton Baltimore/White Marsh

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 Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. Make sure you have lots of time for activities like Rolphs Wharf Marina and Crumpton Auction.