Find Family Hotels in Chestertown, MD from CA $101
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Our top choices for Chestertown family-friendly hotels
8.6 out of 10, Excellent, (890 reviews)
- Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.
The price is CA $150
CA $166 total
includes taxes & fees
Mar 29 - Mar 30
7.2 out of 10, Good, (430 reviews)
- Cozy family retreat with free Wi-Fi, cribs, and premium TV entertainment for memorable stays in the heart of Chestertown.
The price is CA $93
CA $103 total
includes taxes & fees
Mar 29 - Mar 30
5.2 out of 10, (175 reviews)
- Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
The price is CA $93
CA $104 total
includes taxes & fees
Mar 24 - Mar 25
9.6 out of 10, Exceptional, (725 reviews)
The price is CA $187
CA $207 total
includes taxes & fees
Mar 24 - Mar 25
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (973 reviews)
- Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
The price is CA $167
CA $186 total
includes taxes & fees
Mar 30 - Mar 31
8.0 out of 10, Very good, (1,007 reviews)
The price is CA $139
CA $154 total
includes taxes & fees
Mar 29 - Mar 30
7.0 out of 10, Good, (867 reviews)
The price is CA $77
CA $86 total
includes taxes & fees
Mar 29 - Mar 30
La Quinta Inn & Suites by Wyndham Aberdeen-APG
La Quinta Inn & Suites by Wyndham Aberdeen-APGAberdeen
9.0 out of 10, Wonderful, (1,003 reviews)
- Splash into family fun at Aberdeen's seasonal outdoor pool where comfortable rooms await after sun-filled adventures in the park.
The price is CA $117
CA $131 total
includes taxes & fees
Mar 30 - Mar 31
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.
Top Chestertown Hotel Reviews
Hampton Inn & Suites Edgewood/Aberdeen-South
8/10 Good
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