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Family Hotels & Resorts in Chestertown from AU$136

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Check availability on Chestertown Family Hotels

Best Chestertown Family Hotels

Our top choices for Chestertown family-friendly hotels

Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (283)
"Friendly staff, comfortable bed and clean room "
The price is AU$175
includes taxes & fees
19 Oct - 20 Oct
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express White Marsh by IHG
Free continental breakfast

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (935)
"Very clean, friendly, great breakfast!"
The price is AU$175
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn Express White Marsh by IHG
The Lodge at Great Oak Landing
Children’s play area – outdoor

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (68)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is AU$223
includes taxes & fees
30 Sept - 1 Oct
The Lodge at Great Oak Landing
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, (903)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is AU$214
includes taxes & fees
21 Oct - 22 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (820)
"Friendly staff, clean room, convenient location. "
The price is AU$188
includes taxes & fees
28 Sept - 29 Sept
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (396)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is AU$136
includes taxes & fees
1 Oct - 2 Oct
Red Roof Inn & Suites Chestertown
First Floor Studio Apartment in Historic Chestertown
Outdoor pool

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (101)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is AU$244
includes taxes & fees
29 Sept - 30 Sept
First Floor Studio Apartment in Historic Chestertown
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (834)
"Decent for a Hampton Inn"
The price is AU$184
includes taxes & fees
30 Sept - 1 Oct
Hampton Inn Middletown
Quality Inn
Lobby

Quality Inn

2.5 star property
7.8 out of 10, Good, (831)
"Great place and great staff"
The price is AU$174
includes taxes & fees
26 Oct - 27 Oct
Quality Inn
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, (1014)
"Loved our stay! Will visit again soon!!! "
The price is AU$152
includes taxes & fees
6 Oct - 7 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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

The Inn at Henderson's Wharf, an Ascend Collection Hotel

The Inn at Henderson's Wharf, an Ascend Collection Hotel

10/10 Excellent
" Very nice"
Marta 2-night trip
Posted 3 days ago
The Inn at Henderson's Wharf, an Ascend Collection Hotel

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 sporting events 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 Garfield Center for the Arts at the Prince Theater and Crumpton Auction.

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