
Find Hotels with a Pool in Chestertown, MD
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9 Oct - 11 OctOur 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.
SAR 389
SAR 432 total
includes taxes & fees
25 Oct - 26 Oct




2. 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.
SAR 372
SAR 596 total
includes taxes & fees
1 Oct - 2 Oct




3. 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.
SAR 405
SAR 464 total
includes taxes & fees
1 Oct - 2 Oct




4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Cozy 1-bedroom in-law suite in lovely Chestertown with ACChestertown
SAR 826
SAR 1,158 total
includes taxes & fees
7 Oct - 8 Oct




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.
SAR 677
SAR 752 total
includes taxes & fees
4 Oct - 5 Oct




6. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
- Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
SAR 571
SAR 633 total
includes taxes & fees
6 Oct - 7 Oct




7. 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.
SAR 413
SAR 458 total
includes taxes & fees
25 Oct - 26 Oct




8. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MDBel Air
- Seasonal outdoor pool beckons with umbrella-shaded lounging spots perfect for refreshing dips amid Maryland's summer sun.
SAR 353
SAR 395 total
includes taxes & fees
25 Oct - 26 Oct
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Top Chestertown Hotel Reviews
Hampton Inn & Suites Edgewood/Aberdeen-South
10/10 Excellent
"Nice room. Nice stay."
Red Roof Inn & Suites Chestertown
10/10 Excellent
"Perfectly adequate room for a visit to Chestertown. Good furnishings and amenities. Walkable to stores and restaurants."







