The Best Hotels with a Pool in Chestertown, MD from ￥15,769 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 Johns Hopkins Hospital. Provides buffet, an indoor pool, and free self parking. Blue Heron Farm Waterfront Chalet : Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool, and spa services. Historic Inns of Annapolis : 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.

￥24,092 total

includes taxes & fees

Jun 3 - Jun 4

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.

￥18,769 total

includes taxes & fees

Jun 21 - Jun 22

First Floor Studio Apartment in Historic Chestertown

Chestertown

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

￥25,299 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.

￥18,784 total

includes taxes & fees

Jun 16 - Jun 17

Best Western Kent Narrows Inn

Grasonville

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

￥20,345 total

includes taxes & fees

Jun 7 - Jun 8

Kent Island Resort

Stevensville

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

￥32,971 total

includes taxes & fees

Jun 15 - Jun 16

Inn at Huntingfield Creek

Rock Hall

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

￥31,482 total

includes taxes & fees

Jun 4 - Jun 5

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

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

￥17,406 total

includes taxes & fees

Jun 14 - Jun 15

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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 Baltimore/Glen Burnie

8/10 Good

"Nice and clean"

Red Roof Inn & Suites Chestertown

2/10 Terrible

"The staff at the front is very rude. Everytime I would go to the front I would have to say hello multiple times for somebody to come to the front to assist me. There was a guy on night shift with black glasses, would always say Jesus Christ or would mumble under his breath because it seemed like I was bothering him. The tv wasn’t working another night so I went to the front, and the lady told me it is what it is. This place is very unprofessional. The towels and washcloths were still dirty looking. Will not be back."

Fairfield Inn & Suites by Marriott White Marsh

6/10 Okay

"Unfortunately, the room did not live up to the reviews. Maybe it was just our room, but the carpet had a stain and needed replacing. The mattress was meh. The bathroom needed updating. It had the best reviews of the hotels in the area, and I changed my mind based on the reviews. I wish I hadn't. Perhaps some of my feelings are due to the couple next door who were screaming at each other for an hour (at 10pm!). I called the front desk to complain, and the couple eventually quieted down. It just wasn't a good night."

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 Johns Hopkins Hospital. Provides buffet, an indoor pool, and free self parking. Blue Heron Farm Waterfront Chalet: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool, and spa services. Historic Inns of Annapolis: 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, 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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