Chestertown Hotel Guide - Family Friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Family Friendly Hotels

Tonight
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Chestertown Family Friendly Hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
  • Cots/infant beds
8.6 out of 10, Excellent, (857)
Seasonal outdoor pool adventure awaits families with young explorers at this Chestertown haven. Pool gates ensure child safety while premium TV channels and blackout drapes guarantee entertainment and rest. Free breakfast and proximity to the dog park complete this family retreat.
The price is €98
includes taxes & fees
4 Dec - 5 Dec
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
  • Cots/infant beds provided
7.2 out of 10, Good, (417)
Minutes from Chestertown Dog Park, this family-friendly hotel offers spacious, quiet rooms with premium channels and pay films for kids. Parents appreciate the complimentary cots, free parking, and helpful staff who create stress-free family holidays in comfortable surroundings.
The price is €69
includes taxes & fees
11 Dec - 12 Dec
Red Roof Inn & Suites Chestertown
Outdoor pool
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
  • Outdoor pool
9.6 out of 10, Exceptional, (107)
The price is €141
includes taxes & fees
11 Dec - 12 Dec
First Floor Studio Apartment in Historic Chestertown
Front of property – evening/night
Driftwood Inn

Driftwood Inn

2.0 star property
Chestertown
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
5.2 out of 10, (175)
Family holidays thrive at this spotless Chestertown hotel where housekeeping service earns rave reviews. Kids can enjoy premium TV channels while parents appreciate the convenience of in-room refrigerators, microwaves, and complimentary Wi-Fi. Free parking completes this practical family escape.
The price is €61
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn
Arcade
Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG

2.5 star property
Aberdeen
  • Cots/infant beds provided
  • Arcade/games room
8.6 out of 10, Excellent, (425)
Children delight in splashing through the indoor swimming pool before challenging each other in the vibrant arcade room. Complimentary breakfast fuels exploration of nearby Susquehanna State Park, just an 8-minute drive away. Cots available upon request.
The price is €106
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn Express Aberdeen by IHG
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
Aberdeen
  • Cots/infant beds provided
9.0 out of 10, Wonderful, (1014)
Kids delight in the seasonal outdoor pool while parents appreciate the well-maintained grounds and comfortable accommodation. Just minutes from Susquehanna State Park, this hotel offers complimentary breakfast, cots, and premium TV channels for family downtime.
The price is €89
includes taxes & fees
30 Nov - 1 Dec
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Lobby
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
  • Indoor pool
9.2 out of 10, Wonderful, (308)
The price is €101
includes taxes & fees
7 Dec - 8 Dec
Fairfield Inn & Suites by Marriott Middletown
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
  • Cots/infant beds
  • Indoor pool
8.8 out of 10, Excellent, (856)
Families cherish the spacious, comfortable rooms with cots available upon request and blackout drapes for solid naps. The indoor swimming area delights children while parents appreciate the fitness centre, 20 nearby restaurants, and exceptionally friendly staff.
The price is €99
includes taxes & fees
4 Dec - 5 Dec
Hampton Inn Middletown
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
7.8 out of 10, Good, (855)
The price is €81
includes taxes & fees
14 Dec - 15 Dec
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
  • Indoor pool
8.0 out of 10, Very good, (1008)
The price is €88
includes taxes & fees
11 Dec - 12 Dec
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Amazing staff. Clean room."
Cindy 1-night trip
Posted 1 day ago
Best Western Plus Hotel & Conference Center

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