TOP Hotels with 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 Johns Hopkins Hospital. Provides 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. Hampton Inn Baltimore/Glen Burnie : Offers complimentary high-speed (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.

Rp2.693.158 total

includes taxes & fees

4 Jun - 5 Jun

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.

Rp2.118.653 total

includes taxes & fees

2 Jul - 3 Jul

Kent Island Resort

Stevensville

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

Rp3.685.818 total

includes taxes & fees

16 Jun - 17 Jun

Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Smyrna

Dip into poolside bliss at this hotel with a sun-soaked outdoor pool and modern fitness centre nearby.

Rp1.799.808 total

includes taxes & fees

17 Jun - 18 Jun

Inn at Huntingfield Creek

Rock Hall

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

Rp3.519.336 total

includes taxes & fees

4 Jun - 5 Jun

Best Western Kent Narrows Inn

Grasonville

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

Rp2.274.389 total

includes taxes & fees

22 Jun - 23 Jun

La Quinta Inn & Suites by Wyndham Aberdeen-APG

Aberdeen

Splash into summer at this hotel with a sparkling seasonal outdoor pool and tranquil landscaped grounds.

Rp1.762.838 total

includes taxes & fees

21 Jun - 22 Jun

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

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

Rp1.945.900 total

includes taxes & fees

14 Jun - 15 Jun

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Choose what matters most at hotels with a pool in Chestertown

Breakfast included

Hot tub

Top Chestertown Hotel Reviews

Red Roof Inn & Suites Chestertown

8/10 Good

"Towels might be too old? Must have been cleaned bath towels. But there are yellow stains. I did not feel like using them."

Hampton Inn Baltimore/Glen Burnie

2/10 Terrible

"There were people sitting outside the hotel who appeared to be smoking weed, which made us feel uncomfortable and a little scared, especially since we had planned to stay there with family. When we entered the room, there was a musty smell. The blankets also caused some itching, which made the stay even more uncomfortable. The worst part was that the toilet got clogged in the morning, which was unbearable and very disappointing."

Pendry Baltimore

10/10 Excellent

"Staff, especially Terrance, Brittany, and Issa, were exceptional! Their kindness and professionalism were extremely helpful!! Also, a big shout out to the housekeepers-the rooms and other spaces were spectacular!! Sadly it rained most of our trip and we could not enjoy the outdoor pool. The ducks did tho!"

Hilton Garden Inn Baltimore/White Marsh

2/10 Terrible

"Checked into room only to find out the plumbing at the hotel was being worked on and there was no water until later in our rooms. Once the water came on, it was brown until the next morning. Out relatives had to change rooms because their toilet was not working and the room smelled like sewage. I couldn't sleep in my bed because the broken bed frame was repaired by someone who never did carpentry ever before... There was three 2x4s in the center of the bed, causing the mattress to have a high bump in the center. Our bathroom looked like a highway motel bathroom. Missing lights, broken floor tiles. It was confusing because I booked this hotel thinking it was an upgrade for our Baltimore visit. The only thing nice was the lobby and pool. My niece and nephew loved the pool. When checking out, they asked "how was everything". I told them they don't want to know, they said they did... So I gave them the list, and they were shocked. It is their hotel, they know the shape it is in... I will never book this hotel again."

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. Provides 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. Hampton Inn Baltimore/Glen Burnie: Offers 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, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater 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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