Hotels with Pool & Resorts in Chestertown from AU$126

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Check availability on Chestertown Hotels with Pool

Tonight
3 Mar - 4 Mar
Tomorrow
4 Mar - 5 Mar
This weekend
6 Mar - 8 Mar
Next weekend
13 Mar - 15 Mar

Our top choices for Chestertown hotels with a pool

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 AU$174
includes taxes & fees
16 Mar - 17 Mar
The Lodge at Great Oak Landing
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, (879 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is AU$158
includes taxes & fees
15 Mar - 16 Mar
Comfort Inn & Suites Chestertown
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)
"Everything was clean and neat and welcoming "
United States
Iriana J.
The price is AU$226
includes taxes & fees
16 Mar - 17 Mar
First Floor Studio Apartment in Historic Chestertown
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,004 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is AU$147
includes taxes & fees
16 Mar - 17 Mar
Best Western Kent Narrows Inn
Indoor pool

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (351 reviews)
"Consistently a good stay here with helpful staff and comfortable rooms. "
United States
Mary
The price is AU$155
includes taxes & fees
15 Mar - 16 Mar
Fairfield Inn & Suites by Marriott Middletown
Outdoor pool, pool loungers

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (61 reviews)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
Inn at Huntingfield Creek
Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,004 reviews)
"Great stay"
United States
Edward
The price is AU$126
includes taxes & fees
2 Apr - 3 Apr
Quality Inn Smyrna
Indoor pool

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (350 reviews)
"Awesome staff, very clean, great pool Awesome breakfast!!! All good things"
United States
Patty
The price is AU$154
includes taxes & fees
22 Mar - 23 Mar
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Indoor pool

Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (438 reviews)
"Claudia at the front desk was awesome!! Clean room amd great location. Only downside was the loud traffic you could hear from the road in the room."
United States
Steven
The price is AU$186
includes taxes & fees
7 Mar - 8 Mar
Holiday Inn Express Aberdeen by IHG
Indoor pool

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (226 reviews)
"Had a very pleasant check in with this hotel. Many restaurants are within a mile of the hotel. Very close to I-95. "
United States
Dennis
The price is AU$146
includes taxes & fees
22 Mar - 23 Mar
Courtyard Aberdeen at Ripken Stadium
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
Spa pool

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Top Chestertown Hotel Reviews

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

10/10 Excellent
"Super comfortable and quiet "
Maleek 1-night trip
Posted 1 day ago
Americas Best Value Inn Edgewood

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. Features 2 bars, a seasonal outdoor pool and spa services. Historic Inns of Annapolis: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool and free self parking. Hampton Inn Baltimore/Glen Burnie: 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, 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 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.