Chestertown Hotels with Swimming Pool

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Check availability on Chestertown Hotels with Swimming Pools

Tonight
2 Apr - 3 Apr
Tomorrow
3 Apr - 4 Apr
This weekend
3 Apr - 5 Apr
Next weekend
10 Apr - 12 Apr

Our top choices for Chestertown hotels with a pool

Aerial view

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
The price is RM435
RM497 total
includes taxes & fees
5 Apr - 6 Apr
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
8.6 out of 10, Excellent, (893 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is RM495
RM549 total
includes taxes & fees
19 Apr - 20 Apr
Comfort Inn & Suites Chestertown
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (134 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is RM519
RM697 total
includes taxes & fees
5 Apr - 6 Apr
Kent Island Resort
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is RM400
RM444 total
includes taxes & fees
21 Apr - 22 Apr
Best Western Kent Narrows Inn
Outdoor pool, pool loungers

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is RM564
RM626 total
includes taxes & fees
13 Apr - 14 Apr
Inn at Huntingfield Creek
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (886 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is RM394
RM437 total
includes taxes & fees
5 Apr - 6 Apr
Quality Inn Grasonville near Kent Island
Seasonal outdoor pool

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into summer at this hotel with a sparkling seasonal outdoor pool and tranquil landscaped grounds.
The price is RM356
RM399 total
includes taxes & fees
20 Apr - 21 Apr
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Indoor pool

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (325 reviews)
  • cleanliness
    Splash into holiday bliss with an indoor pool perfect for year-round swimming at this Aberdeen hotel with continental breakfast.
The price is RM441
RM494 total
includes taxes & fees
19 Apr - 20 Apr
Fairfield Inn & Suites by Marriott Aberdeen
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (977 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is RM475
RM527 total
includes taxes & fees
21 Apr - 22 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG
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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Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"It was very nice. The hotel seems to have a cat who wanders the first floor, and that was very cute. We were treated very well."
Robert 1-night trip
Posted 4 hours ago
Best Western Plus Hotel & Conference Center

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. Historic Inns of Annapolis: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool and spa services. Hampton Inn Baltimore/Glen Burnie: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool and free self parking. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Pendry Baltimore: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access.
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, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater 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.

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