Find Family Hotels in Chestertown, MD
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Sep 19 - Sep 20Tomorrow
Sep 20 - Sep 21Next weekend
Sep 25 - Sep 27In two weeks
Oct 2 - Oct 4Our 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.
NT$3,412
NT$3,787 total
includes taxes & fees
Oct 14 - Oct 15
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.
NT$2,291
NT$2,543 total
includes taxes & fees
Sep 27 - Sep 28
3. Driftwood Inn
Driftwood InnChestertown
- Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
NT$2,021
NT$2,243 total
includes taxes & fees
Sep 20 - Sep 21
4. 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.
NT$3,532
NT$3,921 total
includes taxes & fees
Oct 18 - Oct 19
NT$3,182
NT$3,532 total
includes taxes & fees
Oct 12 - Oct 13
NT$3,702
NT$4,109 total
includes taxes & fees
Sep 28 - Sep 29
NT$4,837
NT$5,369 total
includes taxes & fees
Oct 4 - Oct 5
8. Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
NT$3,787
NT$4,204 total
includes taxes & fees
Sep 27 - Sep 28
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Top Chestertown Hotel Reviews
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
8/10 Good
"Clean room"
Hilton Garden Inn Kent Island Marina
8/10 Good
"No free breakfast but the one I had to pay for was good"
Comfort Inn & Suites Chestertown
10/10 Excellent
"I have stayed at this location a number of times and have been very pleased with my experience each time. Friendly staff, breakfast is good, and I had a chance to use the workout room this time. Very nice as well. I will be returning again soon."
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
8/10 Good
"Was there for the weekend the room was very clean and spacious. The breakfast was good."
Annapolis Waterfront Hotel, Autograph Collection
10/10 Excellent
"This is a great hotel in a great location two great restaurants."
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