Find Hotels with a Pool in Chestertown, MD from CA $135
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Sep 4 - Sep 6Our 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.
CA $148
CA $165 total
includes taxes & fees
Sep 24 - Sep 25
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.
CA $150
CA $171 total
includes taxes & fees
Sep 9 - Sep 10
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.
CA $137
CA $220 total
includes taxes & fees
Sep 2 - Sep 3
4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Cozy 1-bedroom in-law suite in lovely Chestertown with ACChestertown
CA $262
CA $398 total
includes taxes & fees
Sep 3 - Sep 4
5. 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.
CA $251
CA $278 total
includes taxes & fees
Sep 7 - Sep 8
6. 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.
CA $170
CA $188 total
includes taxes & fees
Sep 1 - Sep 2
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.
CA $139
CA $154 total
includes taxes & fees
Sep 28 - Sep 29
8. Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MDAberdeen
- Indoor pool retreat offers relaxing swims with modern amenities and helpful staff around the clock.
CA $135
CA $151 total
includes taxes & fees
Sep 7 - Sep 8
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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."
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