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

Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Our top choices for Chestertown hotels with a pool

Aerial view

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 AED 486
AED 556 total
includes taxes & fees
2 Jul - 3 Jul
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, (929 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is AED 394
AED 437 total
includes taxes & fees
22 Jul - 23 Jul
Comfort Inn & Suites Chestertown
Outdoor pool

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (114 reviews)
  • cleanliness
    Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
The price is AED 364
AED 583 total
includes taxes & fees
6 Jul - 7 Jul
First Floor Studio Apartment in Historic Chestertown
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers

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 AED 545
AED 728 total
includes taxes & fees
5 Jul - 6 Jul
Kent Island Resort
Outdoor pool, sun loungers

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 AED 654
AED 726 total
includes taxes & fees
7 Jul - 8 Jul
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, (927 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is AED 367
AED 408 total
includes taxes & fees
7 Jul - 8 Jul
Quality Inn Grasonville near Kent Island
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,005 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is AED 460
AED 510 total
includes taxes & fees
5 Jul - 6 Jul
Best Western Kent Narrows Inn
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, (347 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 AED 402
AED 450 total
includes taxes & fees
1 Jul - 2 Jul
Fairfield Inn & Suites by Marriott Aberdeen
Indoor pool

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 AED 373
AED 418 total
includes taxes & fees
12 Jul - 13 Jul
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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, (1,000 reviews)
  • cleanliness
    Splash into summer at this hotel with a sparkling seasonal outdoor pool and tranquil landscaped grounds.
The price is AED 344
AED 385 total
includes taxes & fees
6 Jul - 7 Jul
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.
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Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub

Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"We stayed one night for a lacrosse tournament and a trip to Rockville. The room was clean and everything worked well. There isn’t a gym on the property, but there is free use of a Gold’s Gym .6 miles alway from the hotel. This is one of the nicest gyms I have ever been at! The breakfast food was good with eggs, sausage links, potatoes oranges and apples, amongst other common foods. It was a very pleasant stay! Hotel staff was super friendly and helpful! :)"
Michelle 1-night trip
Posted 1 day ago
Hampton Inn Baltimore/Glen Burnie

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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.