Family Hotels & Resorts in Chestertown from NZ$138

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Check availability on Chestertown Family Hotels

Tonight
9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

Our top choices for Chestertown family-friendly hotels

Free daily full breakfast
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (864 reviews)
"Everything was well!"
United States
Ahmed
The price is NZ$197
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn & Suites Chestertown
Lobby lounge
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (426 reviews)
"Clean and friendly staff. Good location."
United States
Robert
The price is NZ$138
includes taxes & fees
22 Jan - 23 Jan
Red Roof Inn & Suites Chestertown
Outdoor pool
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is NZ$275
includes taxes & fees
12 Jan - 13 Jan
First Floor Studio Apartment in Historic Chestertown
Property amenity
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (332 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is NZ$208
includes taxes & fees
9 Feb - 10 Feb
Fairfield Inn & Suites by Marriott Middletown
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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)
"Room was great and staff excellent. "
United States
Robert
The price is NZ$167
includes taxes & fees
31 Jan - 1 Feb
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (948 reviews)
"Great staff, clean room, nice view!"
United States
Quiana
The price is NZ$183
includes taxes & fees
19 Jan - 20 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (870 reviews)
"Amazing stay"
United States
Katiana
The price is NZ$183
includes taxes & fees
9 Feb - 10 Feb
Hampton Inn Middletown
Lobby
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (866 reviews)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is NZ$167
includes taxes & fees
19 Jan - 20 Jan
Quality Inn Grasonville near Kent Island
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,001 reviews)
"Nice place "
United States
Tucker T
The price is NZ$160
includes taxes & fees
22 Jan - 23 Jan
Best Western Kent Narrows Inn
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (695 reviews)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is NZ$224
includes taxes & fees
19 Jan - 20 Jan
Hyatt Place Kent Narrows & Marina
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"H"
William 2-night trip
Posted 2 days ago
Historic Inns of Annapolis

Frequently asked questions

What's Chestertown like for family-friendly holidays?
If you've been thinking about a trip with your children, the historic destination of Chestertown is a good choice. The boating, festivals and wildlife are just a few things that make this an attractive holiday destination for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city centre.
What's the best family accommodation in 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 child-friendly holiday.
When's the best time to book a family-friendly holiday in Chestertown?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What's there to see and do with your family in Chestertown?
While you are holidaying in Chestertown, you and the family may want to see some interesting spots such as Historical Society of Kent County Maryland and Rolphs Wharf Marina. Make sure that you have lots of time for activities such as Crumpton Auction and Garfield Center for the Arts at the Prince Theater.