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
  • Cribs/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 NT$3,179
NT$3,529 total
includes taxes & fees
Nov 23 - Nov 24
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
  • Cribs/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 movies for kids. Parents appreciate the complimentary cribs, free parking, and helpful staff who create stress-free family vacations in comfortable surroundings.
The price is NT$2,244
NT$2,491 total
includes taxes & fees
Nov 30 - Dec 1
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 NT$3,366
NT$3,736 total
includes taxes & fees
Nov 23 - Nov 24
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
  • Cribs/infant beds provided
9.0 out of 10, Wonderful, (1007)
Kids delight in the seasonal outdoor pool while parents appreciate the well-maintained grounds and comfortable accommodations. Just minutes from Susquehanna State Park, this hotel offers complimentary breakfast, cribs, and premium TV channels for family downtime.
The price is NT$2,888
NT$3,234 total
includes taxes & fees
Nov 23 - Nov 24
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
  • Cribs/infant beds
  • Indoor pool
8.8 out of 10, Excellent, (854)
Families cherish the spacious, comfortable rooms with cribs available upon request and blackout drapes for solid naps. The indoor swimming area delights children while parents appreciate the fitness center, 20 nearby restaurants, and exceptionally friendly staff.
The price is NT$3,216
NT$3,570 total
includes taxes & fees
Dec 1 - Dec 2
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
  • Cribs/infant beds provided
9.2 out of 10, Wonderful, (924)
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 cribs.
The price is NT$3,214
NT$3,568 total
includes taxes & fees
Dec 14 - Dec 15
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 NT$2,958
NT$3,283 total
includes taxes & fees
Dec 11 - Dec 12
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 NT$2,755
NT$3,086 total
includes taxes & fees
Nov 23 - Nov 24
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 NT$2,868
NT$3,183 total
includes taxes & fees
Nov 26 - Nov 27
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"."
Kristine 1-night trip
Posted 1 day ago
Historic Inns of Annapolis

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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.