The Best Hotels with a Pool in Chestertown, MD from NT$3,385 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. 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. 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. Hampton Inn Baltimore/Glen Burnie : Offers complimentary wired internet access, an indoor pool, and free self parking.

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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.

NT$4,783 total

includes taxes & fees

Jun 15 - Jun 16

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.

NT$3,764 total

includes taxes & fees

Jul 9 - Jul 10

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.

NT$6,132 total

includes taxes & fees

Jun 15 - Jun 16

Best Western Kent Narrows Inn

Grasonville

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

NT$3,848 total

includes taxes & fees

Jul 6 - Jul 7

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.

NT$4,178 total

includes taxes & fees

Jun 21 - Jun 22

Quality Inn Grasonville near Kent Island

Grasonville

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

NT$3,510 total

includes taxes & fees

Jun 29 - Jun 30

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

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

NT$3,457 total

includes taxes & fees

Jun 21 - Jun 22

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.

NT$4,705 total

includes taxes & fees

Jul 6 - Jul 7

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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 & Suites Edgewood/Aberdeen-South

6/10 Okay

"Room was pretty outdated. Bed wasn’t comfy. AC was far from bed even running at 60 didn’t keep the room cold. Lots of construction on the exit. Very run down sketchy area."

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

4/10 Poor

"The hotel is the worst hotel I have ever stayed in. The check in lady was beyond unprofessional from the first moment. Everything is super dirty and old. The only thing that was good was the breakfast. Good food and clean court. Otherwise I will never stay there again. Also charged me $25 for early checkin when the expedia email clearly stated the check in times. "

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 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. 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. Hampton Inn Baltimore/Glen Burnie: Offers complimentary 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 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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