Find Hotels with a Pool in Chestertown, MD

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Top Chestertown Hotels with a Pool

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

3.5 star property
Chestertown
8.0 out of 10, Very Good, (76)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Dec 8 - Dec 9
Total with taxes and fees
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, (858)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
$102 nightly
The price is $113
Dec 25 - Dec 26
Total with taxes and fees
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, (107)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 8 - Dec 9
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
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, (644)
"This was a great relaxing stay"
United States
Pamela
$91 nightly
The price is $101
Dec 28 - Dec 29
Total with taxes and fees
Holiday Inn Express & Suites Middletown by IHG
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (597)
"very pet friendly!!"
United States
larry
$90 nightly
The price is $101
Dec 13 - Dec 14
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen
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, (314)
"One of the best hotels I have ever stayed "
United States
jean
$108 nightly
The price is $120
Dec 14 - Dec 15
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Indoor pool
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1005)
"Would stay again"
United States
Dena
$82 nightly
The price is $91
Dec 14 - Dec 15
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (337)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
$80 nightly
The price is $90
Dec 19 - Dec 20
Total with taxes and fees
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Free daily self-serve breakfast
Quality Inn

Quality Inn

2.5 star property
Smyrna
7.6 out of 10, Good, (1000)
"Everything was great!! Checked in with ease and staff was great!!"
United States
Tonya
$63 nightly
The price is $70
Dec 14 - Dec 15
Total with taxes and fees
Quality Inn
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, (1001)
"The room was very nice as well as the staff. The guy at the desk let us check in early which was super helpful for us! Would definitely recommend and come back to again! "
United States
Sara
$84 nightly
The price is $94
Dec 28 - Dec 29
Total with taxes and fees
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Good stay "
D 3-night trip
Posted 3 days ago
Quality Inn & Suites Bel Air I-95 Exit 77A

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. Features 2 bars, a seasonal outdoor pool, and spa services. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Provides complimentary wired internet access, 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, 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 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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