Book the Best Hotels with POOL in Chestertown in 2026

Q: What are some accommodations with pools in Chestertown?

Comfort Inn & Suites Chestertown : Features full, a seasonal outdoor pool, and free self parking. The Lodge at Great Oak Landing : Offers free self parking, a seasonal outdoor pool, and sun loungers. Red Roof Inn & Suites Chestertown : Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool, and free self parking. Historic Inns of Annapolis : Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool, and spa services. Best Western Plus Hotel & Conference Center : Features free self parking, an indoor pool, and televisions.

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.

CA $209 total

includes taxes & fees

Jul 19 - Jul 20

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.

CA $172 total

includes taxes & fees

Jul 26 - Jul 27

Quality Inn Grasonville near Kent Island

Grasonville

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

CA $157 total

includes taxes & fees

Jul 27 - Jul 28

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.

CA $278 total

includes taxes & fees

Jul 29 - Jul 30

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.

CA $187 total

includes taxes & fees

Jul 19 - Jul 20

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

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

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

CA $173 total

includes taxes & fees

Aug 3 - Aug 4

Best Western Kent Narrows Inn

Grasonville

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

CA $197 total

includes taxes & fees

Aug 12 - Aug 13

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Edgewood

Splash into a refreshing escape at this Edgewood hotel, where pool relaxation awaits after adventure-filled days.

CA $141 total

includes taxes & fees

Aug 13 - Aug 14

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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 Kent Island Marina

10/10 Excellent

"Me and my husband went for a one year anniversary. Staying at the hilton was wonderful relaxing, everyone was so pleasant and helpful.The restaurants nearby were great. I love the view we'll be coming back again."

Best Western Plus Hotel & Conference Center

8/10 Good

"We booked the executive king Jacuzzi room. The room was clean very spacious. The Jacuzzi was a little difficult to get into with the steps. They felt a little slippery. The shower was built into the Jacuzzi so there was no curtain and water did sprinkle everywhere which made the floor slippery. We were a little disappointed. The pool was out of order. The hot tub was out of order due to a maintenance thing and we weren’t told until we went down to go swimming. The pool was one of the main reasons why we booked that particular hotel the breakfast was great. The restaurant was good the convenience store I couldn’t find and I have no idea where the comedy club was. If you drive there, there’s lots of restaurants and stores nearby. However, if you Uber or don’t have a car, we had to DoorDash anything we needed."

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good

"Good parking. Room was pretty clean. A/C could of worked a little better. Breakfast was good, but not stocked often, ran out sausage & eggs, low selection of yogurt. No dog poo bags in dog poo bag container, but had trash receptacles for your own. Some people did not clean up after their pet. Some people had issues with elevator, our room was on 1st floor. No guide for TV channels, not a very large selection, wasnt able to use any of our subscription accounts either. Their contract had expired. Rain had electricity & cable flickering on/off for bit. The wall outlet the lamp between our beds was plugged into blew. Just plugged lamp into outlet on plug to alarm clock. No fan in bathroom. Hairdryer screws coming out of wall. Beds and pillows comfortable. Freezer covered with ice, but functional. Check in/out was easy & quick. Saw out of order signs on at least 1 machine in gym area. Looked to have a nice work station setup. No pool. No reading/information on local restaurants, attractions, etc., like you find in most hotels. Worth the nightly fee of $80 a night, no additional pet fee, and free breakfast."

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. The Lodge at Great Oak Landing: Offers free self parking, a seasonal outdoor pool, and sun loungers. Red Roof Inn & Suites Chestertown: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool, and free self parking. Historic Inns of Annapolis: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool, and spa services. Best Western Plus Hotel & Conference Center: Features free self parking, an indoor pool, and televisions.

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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