TOP Hotels with Swimming Pool in Chestertown, MD for 2026

Q: What are some accommodation options 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 sunloungers. The Lodge at Great Oak Landing : 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. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh : Features a sauna, an indoor pool and full.

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

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Our top choices for Chestertown hotels with a pool

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Comfort Inn & Suites Chestertown

Chestertown

Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.

₹11,410 total

includes taxes & fees

20 Aug - 21 Aug

The Lodge at Great Oak Landing

Chestertown

Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.

₹11,840 total

includes taxes & fees

3 Aug - 4 Aug

Inn at Huntingfield Creek

Rock Hall

Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.

₹19,205 total

includes taxes & fees

17 Aug - 18 Aug

Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.

₹12,517 total

includes taxes & fees

19 Aug - 20 Aug

Best Western Kent Narrows Inn

Grasonville

Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.

₹12,718 total

includes taxes & fees

30 Jul - 31 Jul

Quality Inn Grasonville near Kent Island

Grasonville

Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.

₹10,644 total

includes taxes & fees

24 Aug - 25 Aug

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Bel Air

Seasonal outdoor pool beckons with umbrella-shaded lounging spots perfect for refreshing dips amid Maryland's summer sun.

₹9,569 total

includes taxes & fees

3 Aug - 4 Aug

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

Indoor pool retreat offers relaxing swims with modern amenities and helpful staff around the clock.

₹10,480 total

includes taxes & fees

9 Aug - 10 Aug

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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 Kent Narrows Inn

10/10 Excellent

"Hotel was conveniently close to the Jetty. Couldn’t get into room for ice on second floor, had to go to 1st floor,(this was very late at night). No cart in lobby when we checked in. Had to lug everything upstairs without a cart. We found a luggage cart when we were walking to ice machine on first floor."

Quality Inn & Suites Bel Air I-95 Exit 77A

8/10 Good

"Tha manager was friendly and the rooms were clean. The continental breakfast was good (we made fresh waffles) but the coffee was terrible. It was a drama-free environment and quiet. The beds could be better, but most hotels in the area suffer from the same problem. All in all I would return again. It did take too long to return my room deposit, but they did return it, so that's good."

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. Red Roof Inn & Suites Chestertown: Provides free self parking, a seasonal outdoor pool and sunloungers. The Lodge at Great Oak Landing: 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. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Features a sauna, an indoor pool and full.

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, Chestertown Historic District and Rolphs Wharf Marina 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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