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Find Family Hotels in Chestertown, MD

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Check availability on Chestertown Family Hotels

Tonight
Aug 5 - Aug 6
Tomorrow
Aug 6 - Aug 7
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Chestertown Family Hotels

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, (878)
"Great stay beautiful view"
The price is NT$4,156
NT$4,613 total
includes taxes & fees
Aug 12 - Aug 13
Holiday Inn Express Annapolis East-Kent Island by IHG
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (818)
"Front desk service was exceptional!!"
The price is NT$3,278
NT$3,639 total
includes taxes & fees
Aug 14 - Aug 15
Hampton Inn Middletown
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (791)
"It was a clean comfortable spot to rest for the night. "
The price is NT$3,287
NT$3,648 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Inn & Suites Chestertown
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.0 out of 10, Wonderful, (1006)
"It’s safe & comfortable to stay there"
The price is NT$2,897
NT$3,245 total
includes taxes & fees
Aug 19 - Aug 20
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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
7.2 out of 10, Good, (384)
"Good location."
The price is NT$2,153
NT$2,389 total
includes taxes & fees
Aug 11 - Aug 12
Red Roof Inn & Suites Chestertown
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, (738)
"clean, nice staff, nice breakfast"
The price is NT$2,770
NT$3,102 total
includes taxes & fees
Aug 14 - Aug 15
Comfort Inn & Suites Aberdeen near APG
Holiday Inn Express Aberdeen by IHG
Terrace/patio

Holiday Inn Express Aberdeen by IHG

2.5 star property
8.6 out of 10, Excellent, (404)
"Great staff"
The price is NT$3,229
NT$3,616 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Aberdeen by IHG
Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
7.8 out of 10, Good, (1003)
"Great place to stay highly recommend it "
The price is NT$2,917
NT$3,370 total
includes taxes & fees
Aug 31 - Sep 1
Hilton Garden Inn Baltimore/White Marsh
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1824)
"Loved the hotel-great location "
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Free daily buffet breakfast

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3.0 star property
7.0 out of 10, Good, (1007)
"I loved my stay"
The price is NT$2,326
NT$2,686 total
includes taxes & fees
Aug 10 - Aug 11
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Check in took a few extra minutes since there was only one staff member and several checking in. "
Wendy 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott 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.
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.