The Best Hotels with a Pool in Chestertown, MD from ₩150,242 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 3 bars, a seasonal outdoor pool, and free self parking. 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 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.

Stephen

₩229,533 total

includes taxes & fees

May 27 - May 28

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.

Anita

₩186,498 total

includes taxes & fees

Jun 24 - Jun 25

Inn at Huntingfield Creek

Rock Hall

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

Cristy

₩299,947 total

includes taxes & fees

Jun 8 - Jun 9

Kent Island Resort

Stevensville

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

David

₩316,398 total

includes taxes & fees

Jun 1 - Jun 2

Quality Inn Grasonville near Kent Island

Grasonville

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

Samantha

₩171,793 total

includes taxes & fees

May 27 - May 28

Best Western Kent Narrows Inn

Grasonville

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

Elizabeth-Ann

₩193,843 total

includes taxes & fees

Jun 1 - Jun 2

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.

Richard

₩184,696 total

includes taxes & fees

Jun 7 - Jun 8

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

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

Patty

₩165,847 total

includes taxes & fees

Jun 7 - Jun 8

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Choose what matters most at hotels with a pool in Chestertown

Breakfast included

Hot tub

Top Chestertown Hotel Reviews

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

6/10 Okay

"Black mold in the shower"

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

6/10 Okay

"The elevator wasn’t working. I’m disabled and my room was on the 3rd floor. The lobby smells terrible. Idk if it was the staffs body odor or what. Terrible. Smell. Rest of the hotel and room smelled fresh but heavily masked by spray and product but ok. Breakfast area smelled like mold and waffles. Very weird. Idk if I’ll stay again."

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent

"Nice hotel in an excellent location. Love going to the Avenue At White Marsh. Great shops & restaurants only about a mile away. When we checked in, the front desk staff accommodated us when we asked to change rooms. Nice breakfast. Easy parking. We would stay here again."

Comfort Inn & Suites Chestertown

4/10 Poor

"I called the central reservation desk to extend my stay at 08000 the morning of check-in. They verified the reservation under the current ID was extended. When I confirmed this with the front desk, she said they were no rooms available. There was no discussion and she and the next clerk gave no explanation. There were no positive interactions. Just 'We don't have any rooms". I had to come down to the desk after getting in my night clothes as there were no linens for the pull out bed. I had to carry them up by myself. No offer to help with the task. This was NOT a customer friendly place. There are no other places to stay in this little town, so I guess they dont have to try!!!!! NEVER AGAIN"

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 3 bars, a seasonal outdoor pool, and free self parking. 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 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 Rolphs Wharf Marina, 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 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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