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Find Family Hotels in Chestertown, MD

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Check availability on Chestertown Family Hotels

Top Chestertown Family Hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (844)
"This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay."
United States
Paula
The price is ￥15,649
￥17,371 total
includes taxes & fees
Nov 16 - Nov 17
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (414)
"This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement."
United States
Derek
The price is ￥11,047
￥12,262 total
includes taxes & fees
Dec 12 - Dec 13
Red Roof Inn & Suites Chestertown
Outdoor pool
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (105)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
The price is ￥15,261
￥24,485 total
includes taxes & fees
Nov 12 - Nov 13
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown

Chestertown
9.8 out of 10, Exceptional, (27)
"Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!""
United States
Maggie D.
The price is ￥50,629
￥73,533 total
includes taxes & fees
Nov 14 - Nov 15
Newly restored apartment in the heart of Chestertown
Lobby
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
9.2 out of 10, Wonderful, (302)
"Great overall experience "
United States
Clement
The price is ￥16,569
￥18,391 total
includes taxes & fees
Dec 3 - Dec 4
Fairfield Inn & Suites by Marriott Middletown
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, (917)
"The hotel was nice and clean and the staff was always polite and helpful. "
United States
William
The price is ￥15,802
￥17,540 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1003)
"The room was nice the bed comfy, the staff was friendly "
United States
Kenya
The price is ￥14,020
￥15,703 total
includes taxes & fees
Nov 18 - Nov 19
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (850)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
The price is ￥15,833
￥17,576 total
includes taxes & fees
Dec 11 - Dec 12
Hampton Inn Middletown
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (849)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ￥14,345
￥15,922 total
includes taxes & fees
Nov 24 - Nov 25
Quality Inn
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
8.0 out of 10, Very Good, (1000)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is ￥14,118
￥15,671 total
includes taxes & fees
Nov 24 - Nov 25
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

Garner Hotel Glen Burnie BWI Airport Area by IHG

Garner Hotel Glen Burnie BWI Airport Area by IHG

10/10 Excellent
"Clean rooms and great service"
Thomas 1-night trip
Posted 3 days ago
Garner Hotel Glen Burnie BWI Airport Area by IHG

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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 sporting events 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 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.