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Check prices for these dates
Hotels with a Pool in Chestertown
$107
$119 total
includes taxes & fees
Oct 14 - Oct 15
2. The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
- Pool loungers
- Private beach access
$120
$137 total
includes taxes & fees
Sep 20 - Sep 21
3. Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
- Outdoor pool
- Pool loungers
- Full-service spa
$200
$223 total
includes taxes & fees
Sep 20 - Sep 21
4. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
- Pool
- Free parking
- Free WiFi
- Air conditioning
- 24/7 front desk
$100
$111 total
includes taxes & fees
Oct 12 - Oct 13
5. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
- Pool loungers
$111
$123 total
includes taxes & fees
Oct 18 - Oct 19
$116
$129 total
includes taxes & fees
Sep 28 - Sep 29
7. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MDBel Air
- Pool umbrellas
$89
$100 total
includes taxes & fees
Sep 27 - Sep 28
8. Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MDAberdeen
- Indoor pool
$102
$114 total
includes taxes & fees
Sep 27 - Sep 28
9. Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Wingate by Wyndham Bel Air I-95 Exit 77A / APG AreaEdgewood
- Indoor pool
$63
$70 total
includes taxes & fees
Sep 27 - Sep 28
10. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
- Indoor pool
- Pool loungers
$147
$163 total
includes taxes & fees
Oct 5 - Oct 6
11. Ramada Hotel & Conference Center by Wyndham Edgewood
Ramada Hotel & Conference Center by Wyndham EdgewoodEdgewood
- Pool loungers
$84
$94 total
includes taxes & fees
Sep 20 - Sep 21
12. Comfort Inn & Suites Aberdeen near APG
Comfort Inn & Suites Aberdeen near APGAberdeen
- Pool
- Free breakfast
- Pet friendly
- Free parking
- Free WiFi
- Restaurant
$72
$80 total
includes taxes & fees
Sep 29 - Sep 30
13. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
- Indoor pool
- Pool loungers
$152
$169 total
includes taxes & fees
Oct 4 - Oct 5
$115
$129 total
includes taxes & fees
Sep 27 - Sep 28
15. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHGEdgewood
- Pool
- Free breakfast
- Free parking
- Free WiFi
- Connecting rooms available
- Air conditioning
$88
$99 total
includes taxes & fees
Sep 29 - Sep 30
16. Holiday Inn Belcamp - Aberdeen Area by IHG
Holiday Inn Belcamp - Aberdeen Area by IHGBelcamp
- Indoor pool
$93
$104 total
includes taxes & fees
Sep 27 - Sep 28
17. Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
- Indoor pool
$119
$132 total
includes taxes & fees
Sep 27 - Sep 28
$153
$204 total
includes taxes & fees
Oct 12 - Oct 13
$103
$116 total
includes taxes & fees
Sep 27 - Sep 28
$110
$123 total
includes taxes & fees
Sep 27 - Sep 28
Top landmarks in Chestertown
Washington College
8.6/10 (87 reviews)
If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.
Chestertown Historic District
If you're planning a bit of sightseeing during your trip, head to Chestertown Historic District— just one of the landmarks located 0.8 mi (1.2 km) from central Chestertown.
River Arts Chestertown
7.4/10 (6 reviews)
If you'd like to get a taste of Chestertown student life, check out River Arts Chestertown, located 0.7 mi (1.1 km) from central Chestertown.
Rolphs Wharf Marina
8.2/10 (15 reviews)
Imagine strolling along Rolphs Wharf Marina for some great waterfront pics. It's located 3.6 mi (5.8 km) from central Chestertown.
Historical Society of Kent County Maryland
7.4/10 (6 reviews)
Historical Society of Kent County Maryland is 0.7 mi (1.2 km) from central Chestertown, why not stop by during your stay. If you want to experience more of the culture Chestertown has to offer, head to Chestertown Historic District, River Arts Chestertown, and Wilmer Park.
Wilmer Park
8.2/10 (13 reviews)
Wilmer Park is worth a visit, located 1 mi (1.6 km) from central Chestertown.
Kings Town Park
Kings Town Park is worth a visit, located 1.2 mi (1.9 km) from central Chestertown.
Rolling Road Park
Rolling Road Park is worth a visit, located 0.5 mi (0.9 km) from central Chestertown.
About the destination
If you're looking for a place to get away, look no further than Chestertown. Whether you're planning to stay for a night or for the week, the area around Chestertown has accommodations to fit every need. Search for hotels in Chestertown with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Chestertown hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Chestertown hotel deals are here with our lowest price guarantee.