Hotels with Swimming Pools in Chestertown

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Check availability on Chestertown Hotels with Swimming Pools

Top Hotels with Swimming Pools in Chestertown

1 bedroom, free WiFi, bed sheets
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
  • Pool loungers
  • Private beach access
8.0 out of 10, Very good, (76)
Splash into summer fun at the seasonal outdoor pool, complete with loungers and umbrellas for all-day relaxation. Beyond the water, this lodge offers a private beach, 9-hole golf course, and delicious dining at Fairlee's restaurant.
The price is S$148
includes taxes & fees
1 Dec - 2 Dec
The Lodge at Great Oak Landing
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
  • Pool loungers
8.6 out of 10, Excellent, (848)
Poolside relaxation awaits with sun loungers and umbrellas surrounding the seasonal outdoor oasis. After swimming, guests can enjoy the fitness centre, savour a free full breakfast, or explore nearby Washington College and River Arts.
The price is S$148
includes taxes & fees
24 Nov - 25 Nov
Comfort Inn & Suites Chestertown
Indoor pool
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
  • Indoor pool
9.2 out of 10, Wonderful, (305)
Swimming enthusiasts cherish the pristine indoor pool, a centrepiece amenity complemented by exceptional staff service and continental breakfast. Situated near restaurants and attractions, this well-maintained Fairfield Inn & Suites delivers comfort in a convenient location.
The price is S$157
includes taxes & fees
30 Nov - 1 Dec
Fairfield Inn & Suites by Marriott Middletown
Indoor pool
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
  • Indoor pool
9.4 out of 10, Exceptional, (1005)
Swimmers splash into the warmth of a pristine indoor pool, accessible from early morning until evening. Beyond aquatic pleasures, guests enjoy a comprehensive health club, 24-hour service, and peaceful accommodation praised for exceptional cleanliness.
The price is S$119
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites Edgewood/Aberdeen-South
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
  • Indoor pool
9.0 out of 10, Wonderful, (591)
Splash into holiday mode at the pristine indoor swimming pool after enjoying the complimentary breakfast buffet. Clean, comfortable accommodation and exceptionally friendly staff create a peaceful retreat complete with fitness centre and tennis courts.
The price is S$132
includes taxes & fees
19 Dec - 20 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Indoor pool, open 5 AM to 11 PM, pool loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1001)
Waterfront serenity awaits at the indoor pool, complete with comfortable sun loungers and extended hours from 5 AM to 11 PM. Steps from the marina, this hotel combines aquatic pleasure with scenic beauty and a modern fitness centre.
The price is S$148
includes taxes & fees
1 Dec - 2 Dec
Hilton Garden Inn Kent Island Marina
Indoor pool
Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG

2.5 star property
Aberdeen
  • Indoor pool
8.6 out of 10, Excellent, (425)
Swimming enthusiasts dive into year-round comfort at the indoor aquatic haven, a perfect complement to energising workouts at the fitness centre. After pool time, families appreciate the arcade room while enjoying complimentary breakfast each morning.
The price is S$163
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Express Aberdeen by IHG
Indoor pool
TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen

3.0 star property
Aberdeen
  • Indoor pool
9.0 out of 10, Wonderful, (90)
Splash into a sparkling indoor pool designed for year-round enjoyment, with convenient morning-to-evening access hours. Guest rooms feature premium Egyptian cotton bedding and pillowtop mattresses, complemented by delicious free breakfast buffet each morning.
The price is S$148
includes taxes & fees
7 Dec - 8 Dec
TownePlace Suites by Marriott Edgewood Aberdeen
Free daily self-service breakfast
Quality Inn

Quality Inn

2.5 star property
Smyrna
  • Outdoor pool
7.6 out of 10, Good, (1001)
Swimming enthusiasts splash into the inviting outdoor pool, a refreshing centrepiece after workouts in the fitness centre. Friendly staff ensure exceptional service throughout the hotel, complemented by comfortable, clean accommodation just steps from local dining options.
The price is S$99
includes taxes & fees
22 Dec - 23 Dec
Quality Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Clean and quiet "
Jean 1-night trip
Posted 1 day ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Frequently asked questions

What are some accommodation options with pools in Chestertown?
Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool and free self parking. Red Roof Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor pool and free self parking. The Lodge at Great Oak Landing: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool and spa services. Historic Inns of Annapolis: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Provides buffet, an indoor pool and free self parking.
What is there to see and do in Chestertown?
Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Historical Society of Kent County Maryland, Chestertown Historic District and Rolphs Wharf Marina during your stay.
When is the best time to book a hotel with a pool in Chestertown?
You may want to consider a place to stay that has an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August or June, when the average temperature is 23°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 4°C.