Hotels with Pool & Resorts in Chestertown from AU$120

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Check availability on Chestertown Hotels with Pool

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Our top choices for Chestertown hotels with a pool

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 AU$172
includes taxes & fees
20 Apr - 21 Apr
The Lodge at Great Oak Landing

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (109 reviews)
  • cleanliness
    Serene backyard pool with spa pool and golf course views provides ideal relaxation in historic Chestertown.
The price is AU$224
includes taxes & fees
20 Apr - 21 Apr
First Floor Studio Apartment in Historic Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (899 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is AU$182
includes taxes & fees
3 May - 4 May
Comfort Inn & Suites Chestertown

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is AU$217
includes taxes & fees
20 Apr - 21 Apr
Inn at Huntingfield Creek

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and spa pool sanctuary.
The price is AU$154
includes taxes & fees
29 Apr - 30 Apr
Best Western Kent Narrows Inn

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
  • cleanliness
    Splash into waterfront bliss with indoor and outdoor pools at this log cabin retreat.
The price is AU$591
includes taxes & fees
21 Apr - 22 Apr
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (894 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is AU$164
includes taxes & fees
3 May - 4 May
Quality Inn Grasonville near Kent Island

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, (988 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is AU$193
includes taxes & fees
27 Apr - 28 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is AU$278
includes taxes & fees
20 Apr - 21 Apr
Kent Island Resort

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (333 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 AU$171
includes taxes & fees
3 May - 4 May
Fairfield Inn & Suites by Marriott Aberdeen
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.

Choose what matters most at hotels with a pool in Chestertown

Top Chestertown Hotel Reviews

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