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Find Family Hotels in Chestertown, MD

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Check availability on Chestertown Family Hotels

Top Chestertown Family Hotels

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (772)
"Comfortable room, friendly staff. "
The price is SAR 435
SAR 483 total
includes taxes & fees
16 Jul - 17 Jul
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (367)
"Was a decent place to stay for the price. "
The price is SAR 236
SAR 262 total
includes taxes & fees
26 Jun - 27 Jun
Red Roof Inn & Suites Chestertown

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (804)
"Good location. Breakfast was great and plenty of parking. "
The price is SAR 443
SAR 492 total
includes taxes & fees
30 Jun - 1 Jul
Hampton Inn Middletown

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is SAR 1,347
SAR 2,430 total
includes taxes & fees
15 Jul - 16 Jul
5-bedroom vacation home 5 minutes from historic Charlestown

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (850)
"Lovely place and stay…"
The price is SAR 416
SAR 462 total
includes taxes & fees
29 Jun - 30 Jun
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Aberdeen by IHG

2.5 star property
8.6 out of 10, Excellent, (398)
"Front desk staff was welcoming and friendly! "
The price is SAR 462
SAR 517 total
includes taxes & fees
29 Jun - 30 Jun
Holiday Inn Express Aberdeen by IHG

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (701)
"The hotel's location made it convenient for travel to nearby towns, parks and dining options."
The price is SAR 284
SAR 318 total
includes taxes & fees
29 Jun - 30 Jun
Comfort Inn & Suites Aberdeen near APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.2 out of 10, Wonderful, (1000)
"Very clean and friendly staff"
The price is SAR 332
SAR 372 total
includes taxes & fees
29 Jun - 30 Jun
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Travelodge by Wyndham Aberdeen

2.0 star property
6.2 out of 10, (476)
"Although the property was in a convenient location, the bedding was clean, and it was quiet, it appeared that it was “tired” and needed some repair, serious updating, and a deep cleaning. "
The price is SAR 233
SAR 261 total
includes taxes & fees
23 Jun - 24 Jun
Travelodge by Wyndham Aberdeen

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

10.0 out of 10, Exceptional, (38)
"Easy check-in and access to the property. Clean and stocked with everything we needed. Great rental for families!"
The price is SAR 3,189
SAR 5,226 total
includes taxes & fees
22 Jun - 23 Jun
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
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.

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.
How many hotels that welcome families are there in Chestertown?
Expedia has 6 family-friendly hotels and other accommodations in Chestertown.
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 Garfield Center for the Arts at the Prince Theater and Crumpton Auction.