
Find Hotels with a Pool in Chestertown, MD
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Our top choices for Chestertown hotels with a pool

7.8 out of 10, Good, (80 reviews)
cleanliness Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
The price is SAR 489
SAR 559 total
includes taxes & fees
10 May - 11 May

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
9.6 out of 10, Exceptional, (111 reviews)
cleanliness Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
The price is SAR 371
SAR 596 total
includes taxes & fees
4 May - 5 May

8.6 out of 10, Excellent, (909 reviews)
cleanliness Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is SAR 441
SAR 490 total
includes taxes & fees
31 May - 1 Jun

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 SAR 677
SAR 751 total
includes taxes & fees
5 May - 6 May

Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
9.2 out of 10, Wonderful, (380 reviews)
cleanliness Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.
The price is SAR 420
SAR 466 total
includes taxes & fees
18 May - 19 May

7.6 out of 10, Good, (1,001 reviews)
cleanliness Dip into poolside bliss at this hotel with a sun-soaked outdoor pool and modern fitness center nearby.
The price is SAR 310
SAR 344 total
includes taxes & fees
24 May - 25 May

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 SAR 432
SAR 479 total
includes taxes & fees
20 May - 21 May

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!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 SAR 1,312
SAR 1,589 total
includes taxes & fees
4 May - 5 May
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.
Top Chestertown Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South
8/10 Good
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