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Find Family Hotels in Chestertown, MD

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Check availability on Chestertown Family Hotels

Tonight
2 Jul - 3 Jul
Tomorrow
3 Jul - 4 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Top Chestertown Family Hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (775)
"Comfortable room, friendly staff. "
The price is SAR 420
SAR 467 total
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (369)
"Was a decent place to stay for the price. "
The price is SAR 257
SAR 285 total
includes taxes & fees
9 Jul - 10 Jul
Red Roof Inn & Suites Chestertown
Hampton Inn Middletown
Indoor pool

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (809)
"Front desk service was exceptional!!"
The price is SAR 446
SAR 495 total
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn Middletown
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

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 1,346
SAR 2,429 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
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (863)
"Good location - clean hotel."
The price is SAR 446
SAR 495 total
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Aberdeen by IHG
Terrace/patio

Holiday Inn Express Aberdeen by IHG

2.5 star property
8.6 out of 10, Excellent, (401)
"Front desk staff was welcoming and friendly! "
The price is SAR 495
SAR 554 total
includes taxes & fees
6 Jul - 7 Jul
Holiday Inn Express Aberdeen by IHG
Comfort Inn & Suites Aberdeen near APG
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (712)
"The hotel's location made it convenient for travel to nearby towns, parks and dining options."
The price is SAR 316
SAR 353 total
includes taxes & fees
28 Jul - 29 Jul
Comfort Inn & Suites Aberdeen near APG
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.2 out of 10, Wonderful, (1000)
"Very nice hotel . Loved the laundry facilities available for guests . "
The price is SAR 379
SAR 425 total
includes taxes & fees
20 Jul - 21 Jul
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Travelodge by Wyndham Aberdeen
Exterior

Travelodge by Wyndham Aberdeen

2.0 star property
6.2 out of 10, (481)
"Dump"
The price is SAR 236
SAR 265 total
includes taxes & fees
6 Jul - 7 Jul
Travelodge by Wyndham Aberdeen
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Fridge, microwave, oven, stovetop

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 3,188
SAR 5,160 total
includes taxes & fees
14 Jul - 15 Jul
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.