An aerial view of a town with a river, buildings, and surrounding greenery.

Hotels with Swimming Pool in Chestertown, Maryland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Hotels with Swimming Pool

This weekend
Next weekend

Our top choices for Chestertown hotels with a pool

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (89 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
The price is P8,093
P9,254 total
includes taxes & fees
Jul 9 - Jul 10
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (929 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is P6,576
P7,299 total
includes taxes & fees
Jul 23 - Jul 24
Comfort Inn & Suites Chestertown

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (150 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is P10,895
P14,201 total
includes taxes & fees
Jul 6 - Jul 7
Kent Island Resort

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is P10,894
P12,092 total
includes taxes & fees
Jul 6 - Jul 7
Inn at Huntingfield Creek

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (928 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is P6,118
P6,790 total
includes taxes & fees
Jul 7 - Jul 8
Quality Inn Grasonville near Kent Island

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 P7,659
P8,501 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Kent Narrows Inn

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (348 reviews)
  • cleanliness
    Splash into vacation bliss with an indoor pool perfect for year-round swimming at this Aberdeen hotel with continental breakfast.
The price is P6,716
P7,522 total
includes taxes & fees
Jul 2 - Jul 3
Fairfield Inn & Suites by Marriott Aberdeen

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (385 reviews)
  • cleanliness
    Indoor pool retreat offers relaxing swims with modern amenities and helpful staff around the clock.
The price is P6,100
P6,833 total
includes taxes & fees
Jul 8 - Jul 9
Home2 Suites by Hilton Baltimore / Aberdeen, MD

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, (1,002 reviews)
  • cleanliness
    Splash into summer at this hotel with a sparkling seasonal outdoor pool and tranquil landscaped grounds.
The price is P5,742
P6,431 total
includes taxes & fees
Jul 6 - Jul 7
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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 accommodations with pools in Chestertown?
Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool, and free self parking. Red Roof Inn & Suites Chestertown: Provides free self parking, a seasonal outdoor pool, and sun loungers. 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: Hotel located near Johns Hopkins Hospital. Features buffet, an indoor pool, and free self parking. Annapolis Waterfront Hotel, Autograph Collection: Offers free self parking, 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 Chestertown Historic District, 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 offers an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August, or June when the average temperature is 74°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 39°F.

Explore a world of travel with Expedia