Search Family-Friendly Hotels in Chestertown
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27 Aug - 28 AugTomorrow
28 Aug - 29 AugThis weekend
28 Aug - 30 AugNext weekend
4 Sep - 6 SepOur 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.
฿3,516
฿3,903 total
includes taxes & fees
16 Sept - 17 Sept
2. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
- Cosy family retreat with free Wi-Fi, cots, and premium TV entertainment for memorable stays in the heart of Chestertown.
฿2,296
฿2,548 total
includes taxes & fees
30 Aug - 31 Aug
3. Driftwood Inn
Driftwood InnChestertown
- Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
฿2,076
฿2,304 total
includes taxes & fees
28 Aug - 29 Aug
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.
฿4,151
฿4,608 total
includes taxes & fees
9 Sept - 10 Sept
฿3,383
฿3,755 total
includes taxes & fees
22 Sept - 23 Sept
฿5,459
฿6,059 total
includes taxes & fees
8 Sept - 9 Sept
฿3,898
฿4,327 total
includes taxes & fees
7 Sept - 8 Sept
8. Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
฿3,903
฿4,332 total
includes taxes & fees
6 Sept - 7 Sept
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Top Chestertown Hotel Reviews
Hampton Inn Baltimore/White Marsh
10/10 Excellent
"Breakfast was good."
Hampton Inn & Suites Edgewood/Aberdeen-South
10/10 Excellent
"First, the property was conveniently located just off of I-95. Check in at front desk was less than 3 minutes. The room was clean. The included morning breakfast provided a nice selection of items & all were fresh & hot."
La Quinta Inn & Suites by Wyndham Aberdeen-APG
10/10 Excellent
"The room was clean and the pool was well maintained. Breakfast and coffee were very good. Pleasant stay. Easy on and off I95."
Pendry Baltimore
10/10 Excellent
"Loved everything about this hotel."
Annapolis Waterfront Hotel, Autograph Collection
8/10 Good
"The location of the hotel was awesome along with our balcony view. However you should not have to pay an additional $50 per day to park your car especially since the garage up the street is Therefore the guests are getting pentalized to park at the hotel . Additionally the front desk women were rude and condescending"
Holiday Inn Express Annapolis East-Kent Island by IHG
10/10 Excellent
"Very nice hotel in an area of mixed use properties. Convenient to shopping, dining and entertainment"
Comfort Inn & Suites Chestertown
10/10 Excellent
"Our receptionist was very friendly and helpful. The room was clean and modern. Cooling system was good. Nice bathroom. The outdoor pool was clean and quiet and well maintained. Breakfast was standard travel fare but it was very fresh."
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
10/10 Excellent
"Very clean place and will continue to stay here"
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
8/10 Good
"Everything was good. I would suggest flipping around the mattress to prevent one side from losing shape making for an uncomfortable sleep. I did not want to alert the staff or complain. I just slept on the higher side of the bed. Other than that, our stay was nice."