Top 10 Hotels with Pool & Accommodation in Chestertown from NZ$188

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 Johns Hopkins Hospital. Features buffet, an indoor pool and free self parking. Historic Inns of Annapolis : Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool and spa services. Annapolis Waterfront Hotel, Autograph Collection : Provides complimentary high-speed (wired) Internet access, an indoor pool and free self parking.

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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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.

includes taxes & fees

11 June - 12 June

First Floor Studio Apartment in Historic Chestertown

Chestertown

Serene backyard pool with spa pool and golf course views provides ideal relaxation in historic Chestertown.

includes taxes & fees

11 June - 12 June

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.

includes taxes & fees

2 July - 3 July

Best Western Kent Narrows Inn

Grasonville

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

includes taxes & fees

6 July - 7 July

Quality Inn Grasonville near Kent Island

Grasonville

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

includes taxes & fees

11 June - 12 June

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

Kent Island Resort

Stevensville

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

includes taxes & fees

16 June - 17 June

Fairfield Inn & Suites by Marriott Middletown

Middletown

Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.

includes taxes & fees

21 June - 22 June

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.

includes taxes & fees

11 June - 12 June

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Choose what matters most at hotels with a pool in Chestertown

Breakfast included

Spa pool

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

6/10 Okay

"Elevators were down when we stayed. Although originally we were booked a room on the 5th floor, front desk was able to get us a room on the 4th floor…one less flight of stairs to go up and down. With two kids, one being 14 months old, it was a lot to go up and down the stairs. Other than that everything else was ok"

Red Roof Inn & Suites Chestertown

2/10 Terrible

"The staff,( if you want to call them that)don't greet you when you walk in to register, I had to initiate the conversation. The elevator floor was filthy nasty and it creaked and groaned. We got off of the elevator on our floor and was greeted by Marijuana smoke and smell. I went back down to inform the front desk that someone was smoking in their non smoking hotel, she said that there wasn't much they could do about it except spray air fresher or smoke eliminator, I ask why they wouldn't eliminate the smoker, no answer. We were visiting friends and they let us borrow a electric air cleaner for the room. The room, the walls appear to have been painted recently, that and the TV had good reception are the only good things we can say about the room. The carpet was stained and probably hadn't been cleaned for awhile. The couch was nasty, stained and dirty it looked like they got it for free from the side of the road. The handle on the night stand was hanging by one screw. They had one small trash can in the bathroom for the whole room. The bathroom, it was it's own kind of nasty. The door wouldn't latch, there was mold along the top of the tub, the towel rack was loose from the wall. All the things that were wrong were plainly seen by anybody that came in the room to clean. The sheets were clean, the towels were clean. I wouldn't stay here if I were you."

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 Johns Hopkins Hospital. Features buffet, an indoor pool and free self parking. Historic Inns of Annapolis: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool and spa services. Annapolis Waterfront Hotel, Autograph Collection: Provides complimentary high-speed (wired) Internet access, an indoor pool and free self parking.

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 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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