Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

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Dec 23 - Dec 24
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Dec 24 - Dec 25
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Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

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, (861)
"Everything was well!"
United States
Ahmed
$104 nightly
The price is $115
Dec 29 - Dec 30
Total with taxes and fees
Comfort Inn & Suites Chestertown
Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Dec 24 - Dec 25
Total with taxes and fees
The Lodge at Great Oak Landing
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)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 24 - Dec 25
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Free daily continental breakfast
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (562)
"This is my forth time at this hotel. Excellent service . Not staying for breakfast but usually very good"
United States
Carolyn
$82 nightly
The price is $92
Dec 26 - Dec 27
Total with taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
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, (323)
"The room was spotless, courteous staff, and a wonderful breakfast to start my day "
United States
Alan
$108 nightly
The price is $120
Dec 28 - Dec 29
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Free daily self-serve breakfast
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1002)
"Very pleasant experience. "
United States
Kathleen
$69 nightly
The price is $76
Jan 22 - Jan 23, 2026
Total with taxes and fees
Quality Inn Smyrna
Indoor pool
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (866)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
$95 nightly
The price is $106
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hampton Inn Middletown
Property amenity
Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (471)
"Good room and service "
United States
Robert
$83 nightly
The price is $93
Dec 26 - Dec 27
Total with taxes and fees
Candlewood Suites Aberdeen-Bel Air by IHG
Indoor pool
Home2 Suites by Hilton Baltimore / Aberdeen, MD

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, (338)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
$71 nightly
The price is $80
Jan 10 - Jan 11, 2026
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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, (604)
"very pet friendly!!"
United States
larry
$98 nightly
The price is $110
Jan 9 - Jan 10, 2026
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"The welcome bag with water and snack was a total surprise. Great idea and the hot cocoa area nice touch. Little candies and cookies at front desk I enjoyed very much. Definitely will be going back. Thank you "
Lorraine 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott 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. Red Roof Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor pool, and free self parking. The Lodge at Great Oak Landing: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool, and spa services. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Features complimentary 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.
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, Crumpton Auction, 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.

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