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Check availability on Chestertown Family-Friendly Hotels

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, (848)
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 2.688.006 ₫
2.983.687 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains
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, (416)
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 1.897.416 ₫
2.106.132 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Red Roof Inn & Suites Chestertown
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, (305)
The price is 2.845.800 ₫
3.158.838 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Fairfield Inn & Suites by Marriott Middletown
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, (1006)
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 2.441.605 ₫
2.734.650 ₫ total
includes taxes & fees
23 Nov - 24 Nov
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
  • Cots/infant beds
  • Indoor pool
8.8 out of 10, Excellent, (854)
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 2.719.320 ₫
3.018.656 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Hampton Inn 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
  • Cots/infant beds provided
9.2 out of 10, Wonderful, (923)
Splash into family adventures at this waterfront hotel featuring a gated seasonal pool with sun loungers and umbrellas. Kids appreciate premium TV channels while parents love the free breakfast buffet, convenient Matapeake State Park access, and complimentary cots.
The price is 2.714.359 ₫
3.012.939 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (851)
The price is 2.498.791 ₫
2.773.658 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Quality Inn
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

2.5 star property
Aberdeen
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Restaurant
7.8 out of 10, Good, (797)
Family adventures flourish with video game consoles in freshly remodeled rooms and premium TV channels for entertainment day or night. Nearby Ripken Stadium and Susquehanna State Park offer additional recreation beyond the seasonal outdoor pool.
The price is 2.329.605 ₫
2.609.157 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Comfort Inn & Suites Aberdeen near APG
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, (1001)
The price is 2.424.727 ₫
2.691.448 ₫ total
includes taxes & fees
1 Dec - 2 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

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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.
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.