Find Family Hotels in Chestertown, MD
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Chestertown Family Hotels
Tonight
Aug 8 - Aug 9Tomorrow
Aug 9 - Aug 10Next weekend
Aug 14 - Aug 16In two weeks
Aug 21 - Aug 23Our top choices for Chestertown family-friendly hotels
1. Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
- Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.
₩150,923
₩167,525 total
includes taxes & fees
Aug 31 - Sep 1
2. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
- Cozy family retreat with free Wi-Fi, cribs, and premium TV entertainment for memorable stays in the heart of Chestertown.
₩88,695
₩98,451 total
includes taxes & fees
Aug 16 - Aug 17
3. Driftwood Inn
Driftwood InnChestertown
- Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
₩89,399
₩99,240 total
includes taxes & fees
Aug 9 - Aug 10
₩154,133
₩172,629 total
includes taxes & fees
Aug 9 - Aug 10
₩237,928
₩264,100 total
includes taxes & fees
Aug 16 - Aug 17
₩140,786
₩156,272 total
includes taxes & fees
Sep 7 - Sep 8
7. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
- Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
₩167,535
₩185,963 total
includes taxes & fees
Sep 7 - Sep 8
8. Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
₩167,535
₩185,963 total
includes taxes & fees
Aug 9 - Aug 10
View all properties
Top Chestertown Hotel Reviews
Best Western Kent Narrows Inn
8/10 Good
"Convenient location with many restaurants a short walk. Would have liked a better room with a view. Stuck on the backside of hotel,"
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
10/10 Excellent
"Very quiet Very relaxing rooms excellent breakfast excellent"
La Quinta Inn & Suites by Wyndham Aberdeen-APG
8/10 Good
"Clean room for the most part. They were changing some furniture during my stay and the boxes were just off the main lobby. Not dirty or disorganized, just maybe a little odd to walk by on the way to the elevator."
Quality Inn & Suites Bel Air I-95 Exit 77A
10/10 Excellent
"I had no issues except for the first day but my room was moved and I had no issues after that"
Hilton Garden Inn Baltimore/White Marsh
8/10 Good
"Room was good and parking was great"
Hampton Inn & Suites Edgewood/Aberdeen-South
10/10 Excellent
"Front desk staff was great."
Comfort Inn & Suites Chestertown
8/10 Good
"Hotel was fine. Area was a little sketchy."