Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Tonight
Feb 2 - Feb 3
Tomorrow
Feb 3 - Feb 4
This weekend
Feb 6 - Feb 8
Next weekend
Feb 13 - Feb 15

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, (870 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is ₩146,117
₩162,190 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 ₩156,012
₩178,369 total
includes taxes & fees
Mar 1 - Mar 2
The Lodge at Great Oak Landing
Seasonal outdoor pool, open 10:00 AM to 8:30 PM, pool umbrellas

Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
2.0 star property
Edgewood
6.6 out of 10, (521 reviews)
"Clean room, courteous staff, quiet area, convenient location with food and amenities nearby."
United States
Somu
The price is ₩107,258
₩120,130 total
includes taxes & fees
Feb 3 - Feb 4
Ramada Hotel & Conference Center by Wyndham Edgewood
Exterior

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (434 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is ₩225,279
₩286,818 total
includes taxes & fees
Feb 8 - Feb 9
The Inn at Chesapeake Bay Beach Club
Outdoor pool, sun loungers

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
Inn at Huntingfield Creek
Indoor pool, sun loungers

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (710 reviews)
"Room was spotless, staff was exceptionally friendly."
United States
Maxwell
The price is ₩192,126
₩213,260 total
includes taxes & fees
Feb 16 - Feb 17
Hyatt Place Kent Narrows & Marina
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (874 reviews)
"Amazing stay"
United States
Katiana
The price is ₩137,407
₩152,522 total
includes taxes & fees
Feb 10 - Feb 11
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, (660 reviews)
"Clean room and hotel. Breakfast was good, the fresh baked cookies at the front desk were delicious!"
United States
Valerie
The price is ₩130,010
₩144,311 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Express & Suites Middletown by IHG
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 ₩179,940
₩250,269 total
includes taxes & fees
Feb 3 - Feb 4
Kent Island Resort
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, (342 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is ₩139,978
₩155,375 total
includes taxes & fees
Feb 8 - Feb 9
Fairfield Inn & Suites by Marriott Middletown
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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Top Chestertown Hotel Reviews

Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent
"The room layout was very good. Like it was done by someone who actually traveled a lot. Nice small kitchen. Lots of counter space. Several hooks in bathroom. Counter space in bathroom. "
Michael 2-night trip
Posted 21 hours ago
Home2 Suites by Hilton Baltimore/White Marsh

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