Hotels with Swimming Pool, Chestertown Maryland

Q: 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.

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

The Lodge at Great Oak Landing

Chestertown

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

P9,254 total

includes taxes & fees

Jul 9 - Jul 10

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.

P7,299 total

includes taxes & fees

Jul 23 - Jul 24

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers

Kent Island Resort

Stevensville

Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.

P14,201 total

includes taxes & fees

Jul 6 - Jul 7

Inn at Huntingfield Creek

Rock Hall

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

P12,092 total

includes taxes & fees

Jul 6 - Jul 7

Quality Inn Grasonville near Kent Island

Grasonville

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

P6,790 total

includes taxes & fees

Jul 7 - Jul 8

Best Western Kent Narrows Inn

Grasonville

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

P8,501 total

includes taxes & fees

Jul 6 - Jul 7

Fairfield Inn & Suites by Marriott Aberdeen

Aberdeen

Splash into vacation bliss with an indoor pool perfect for year-round swimming at this Aberdeen hotel with continental breakfast.

P7,522 total

includes taxes & fees

Jul 2 - Jul 3

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

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

P6,833 total

includes taxes & fees

Jul 8 - Jul 9

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Choose what matters most at hotels with a pool in Chestertown

Breakfast included

Hot tub

Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent

"First time staying here , myself and four children. Everything was perfect.. plus the indoor pool was a blast."

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! :)"

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.

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