Chestertown Hotel Guide - Hotels with Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with 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

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (866 reviews)
"Everything was well!"
United States
Ahmed
The price is €95
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn & Suites Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown

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 €140
includes taxes & fees
14 Jan - 15 Jan
First Floor Studio Apartment in Historic Chestertown
Indoor pool
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (333 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is €103
includes taxes & fees
27 Jan - 28 Jan
Fairfield Inn & Suites by Marriott Middletown
Indoor pool
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (635 reviews)
"High quality pillows Comfortable bed Clean room Kuerig Big room Strong WiFi Clean shower Good shampoo Excellent towels Plenty of drawers and closet space Comfy chair Great desk space"
United States
John
The price is €76
includes taxes & fees
6 Feb - 7 Feb
Hilton Garden Inn Aberdeen
Seasonal outdoor pool
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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)
"Room was great and staff excellent. "
United States
Robert
The price is €83
includes taxes & fees
30 Jan - 31 Jan
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Indoor pool
Holiday Inn Express & Suites Middletown by IHG

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, (654 reviews)
"Room was great the staff is so friendly every visit !!!!!"
United States
Dennis
The price is €87
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express & Suites Middletown by IHG
Indoor pool
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (870 reviews)
"Amazing stay"
United States
Katiana
The price is €91
includes taxes & fees
12 Feb - 13 Feb
Hampton Inn Middletown
Desk, laptop workspace, iron/ironing board, free WiFi
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,002 reviews)
"Great stay"
United States
Edward
The price is €65
includes taxes & fees
12 Feb - 13 Feb
Quality Inn Smyrna
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (611 reviews)
"Everything looks great. Staff is very nice."
United States
David
The price is €81
includes taxes & fees
26 Jan - 27 Jan
Hampton Inn & Suites Baltimore/Aberdeen
Seasonal outdoor pool, pool umbrellas
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

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, (1,006 reviews)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is €78
includes taxes & fees
1 Feb - 2 Feb
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Profesional staff. Verry clean room. Nice break fast."
Anwar 1-night trip
Posted 4 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South

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. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Hotel located near Baltimore Inner Harbor Marina. Provides 2 bars, a seasonal outdoor pool and spa services. Pendry Baltimore: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Hilton Garden Inn Baltimore/White Marsh: Hotel located near Johns Hopkins Hospital. Features buffet, an indoor pool and free self parking. Historic Inns of Annapolis: Features a snack bar/deli, a seasonal outdoor pool and buffet.
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, Chestertown Historic District and Rolphs Wharf Marina 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.