Chestertown Hotel Guide - Hotels with Pool in Chestertown, Maryland
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11 Sept - 13 SeptOur top choices for Chestertown hotels with a pool
1. Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
- Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
€103
includes taxes & fees
22 Sept - 23 Sept
2. The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
- Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
€106
includes taxes & fees
30 Aug - 31 Aug
3. First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
- Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
€140
includes taxes & fees
2 Sept - 3 Sept
4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Cozy 1-bedroom in-law suite in lovely Chestertown with ACChestertown
€254
includes taxes & fees
10 Sept - 11 Sept
5. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
- Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
€116
includes taxes & fees
1 Sept - 2 Sept
6. Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
- Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
€173
includes taxes & fees
7 Sept - 8 Sept
7. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
- Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
€96
includes taxes & fees
28 Sept - 29 Sept
8. Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
- Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
€111
includes taxes & fees
28 Sept - 29 Sept
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Top Chestertown Hotel Reviews
Hampton Inn & Suites Edgewood/Aberdeen-South
10/10 Excellent
"Perfect for business and quick family stop travels. Staff is amazing and extremely generous. Clean and well stocked."
Holiday Inn Express Annapolis East-Kent Island by IHG
10/10 Excellent
"Great view of the water."
Hampton Inn Baltimore/White Marsh
10/10 Excellent
"Breakfast was good."
Red Roof Inn & Suites Chestertown
10/10 Excellent
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."