Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Our top choices for Chestertown hotels with a pool

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (873 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is ￥15,903
￥17,652 total
includes taxes & fees
Mar 1 - Mar 2
Comfort Inn & Suites Chestertown
Aerial view

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is ￥16,979
￥19,412 total
includes taxes & fees
Mar 1 - Mar 2
The Lodge at Great Oak Landing
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is ￥15,565
￥24,973 total
includes taxes & fees
Feb 10 - Feb 11
First Floor Studio Apartment in Historic Chestertown
Indoor pool

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (343 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is ￥15,565
￥17,277 total
includes taxes & fees
Feb 15 - Feb 16
Fairfield Inn & Suites by Marriott Middletown
Seasonal outdoor pool, pool umbrellas

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,001 reviews)
"We always enjoy our stay here when visiting our family as the facility is clean, comfortable and quiet. Only exception was on one of the days a fire alarm had gone off and scared us awake but it turned out to be a false alarm. "
United States
Cheryle
The price is ￥12,452
￥13,946 total
includes taxes & fees
Mar 1 - Mar 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Indoor pool

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (620 reviews)
"Good customer service and the room was spotless!"
United States
George
The price is ￥13,021
￥14,583 total
includes taxes & fees
Feb 16 - Feb 17
Hampton Inn & Suites Baltimore/Aberdeen
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (132 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is ￥17,010
￥24,279 total
includes taxes & fees
Feb 10 - Feb 11
Kent Island Resort
Seasonal outdoor pool

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,002 reviews)
"Everything was great"
United States
juan
The price is ￥13,364
￥14,968 total
includes taxes & fees
Feb 17 - Feb 18
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (875 reviews)
"Amazing stay"
United States
Katiana
The price is ￥14,955
￥16,600 total
includes taxes & fees
Mar 3 - Mar 4
Hampton Inn Middletown
Indoor pool

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (661 reviews)
"Clean room and hotel. Breakfast was good, the fresh baked cookies at the front desk were delicious!"
United States
Valerie
The price is ￥16,980
￥18,848 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express & Suites Middletown by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub

Top Chestertown Hotel Reviews

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

10/10 Excellent
"The service was good and the room was was clean "
Angela 1-night trip
Posted 6 days ago
Americas Best Value Inn Edgewood

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. Historic Inns of Annapolis: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool, and spa services. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Offers complimentary wired internet access, an indoor pool, and free self parking. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Features buffet, an indoor pool, and free self parking. Hilton Garden Inn Baltimore/White Marsh: Offers a snack bar/deli, 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 Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater, and Chestertown Historic District 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.