Search Family-Friendly Hotels in Chestertown
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11 Sept - 12 SeptTomorrow
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11 Sept - 13 SeptNext weekend
18 Sept - 20 SeptOur 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.
₹9,923
₹11,014 total
includes taxes & fees
4 Oct - 5 Oct
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.
₹6,847
₹7,600 total
includes taxes & fees
17 Sept - 18 Sept
3. Driftwood Inn
Driftwood InnChestertown
- Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
₹6,039
₹6,704 total
includes taxes & fees
13 Sept - 14 Sept
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.
₹11,263
₹12,502 total
includes taxes & fees
6 Oct - 7 Oct
₹9,545
₹10,595 total
includes taxes & fees
5 Oct - 6 Oct
₹11,103
₹12,325 total
includes taxes & fees
28 Sept - 29 Sept
₹14,508
₹16,104 total
includes taxes & fees
4 Oct - 5 Oct
8. Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
₹11,318
₹12,563 total
includes taxes & fees
20 Sept - 21 Sept
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Top Chestertown Hotel Reviews
Historic Inns of Annapolis
10/10 Excellent
"Wonderful hotel in a great location."
Annapolis Waterfront Hotel, Autograph Collection
8/10 Good
"The location was great. We were able to walk everywhere. Considering the price of rooms, the $39 parking fee was high."
Best Western Plus Hotel & Conference Center
8/10 Good
"Free parking was nice. Comfortable bed. Clean room. Good breakfast."
Hampton Inn Baltimore/Glen Burnie
10/10 Excellent
"Excelente estadía volveré"
Best Western Kent Narrows Inn
10/10 Excellent
"The staff was friendly and helpful the amenities were great and the room was clean and comfortable. It was a great value!"
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
8/10 Good
"It was overall a decent stay. Very low shower pressure. Breakfast was good, no hot items(eggs, sausages, etc). Was told the pool was open, but then there was a sign saying it was closed for maintenance. This was the main reason we chose this hotel. The staff was very accommodating and friendly."
Hilton Garden Inn Baltimore/White Marsh
10/10 Excellent
"The staff was very helpful and friendly! The facilities are well maintained and clean. The room was clean and spacious. Overall my ten days stay was great!"