Find Family Hotels in Chestertown, MD

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Check availability on Chestertown Family Hotels

Tonight
Feb 7 - Feb 8
Tomorrow
Feb 8 - Feb 9
Next weekend
Feb 13 - Feb 15
In two weeks
Feb 20 - Feb 22

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, (872 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is ₩148,038
₩164,322 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 ₩105,376
₩116,967 total
includes taxes & fees
Feb 14 - Feb 15
Red Roof Inn & Suites Chestertown
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, (1,001 reviews)
"Everything was great"
United States
juan
The price is ₩125,646
₩140,724 total
includes taxes & fees
Feb 15 - Feb 16
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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, (343 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is ₩144,891
₩160,829 total
includes taxes & fees
Feb 15 - Feb 16
Fairfield Inn & Suites by Marriott 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 ₩124,402
₩138,087 total
includes taxes & fees
Mar 4 - Mar 5
Quality Inn Grasonville near Kent Island
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (875 reviews)
"Amazing stay"
United States
Katiana
The price is ₩139,213
₩154,526 total
includes taxes & fees
Feb 24 - Feb 25
Hampton Inn Middletown
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (711 reviews)
"Amazing location and staff!"
United States
Bobbi J.
The price is ₩172,699
₩191,696 total
includes taxes & fees
Mar 2 - Mar 3
Hyatt Place Kent Narrows & Marina
Arcade

Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (436 reviews)
"Claudia at the front desk was awesome!! Clean room amd great location. Only downside was the loud traffic you could hear from the road in the room."
United States
Steven
The price is ₩172,699
₩193,423 total
includes taxes & fees
Feb 10 - Feb 11
Holiday Inn Express Aberdeen by IHG
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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Choose what matters most at family-friendly hotels in Chestertown

Breakfast included
Pool

Top Chestertown Hotel Reviews

Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent
"Yes "
Ronald 2-night trip
Posted 3 days 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 Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Make sure you have lots of time for activities like Rolphs Wharf Marina and Crumpton Auction.