Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top 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, (857)
"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
The price is AED 375
AED 416 total
includes taxes & fees
4 Dec - 5 Dec
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

3.5 star property
Chestertown
8.0 out of 10, Very Good, (76)
"Very nice rooms, "
United States
Stephania
The price is AED 364
AED 416 total
includes taxes & fees
1 Dec - 2 Dec
The Lodge at Great Oak Landing
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.
The price is AED 364
AED 583 total
includes taxes & fees
1 Dec - 2 Dec
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, (643)
"This was a great relaxing stay"
United States
Pamela
The price is AED 306
AED 339 total
includes taxes & fees
21 Dec - 22 Dec
Holiday Inn Express & Suites Middletown by IHG
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, (309)
"Great overall experience "
United States
Clement
The price is AED 387
AED 430 total
includes taxes & fees
7 Dec - 8 Dec
Fairfield Inn & Suites by Marriott Middletown
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (595)
"Wonderful room and location "
United States
Caren
The price is AED 332
AED 372 total
includes taxes & fees
8 Dec - 9 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Seasonal outdoor pool
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, (1015)
"The room was nice the bed comfy, the staff was friendly "
United States
Kenya
The price is AED 340
AED 381 total
includes taxes & fees
7 Dec - 8 Dec
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (127)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is AED 409
AED 580 total
includes taxes & fees
7 Dec - 8 Dec
Kent Island Resort
Free daily self-serve breakfast
Quality Inn

Quality Inn

2.5 star property
Smyrna
7.6 out of 10, Good, (1003)
"Everything was great!! Checked in with ease and staff was great!!"
United States
Tonya
The price is AED 231
AED 257 total
includes taxes & fees
14 Dec - 15 Dec
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, (1008)
"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
The price is AED 306
AED 342 total
includes taxes & fees
26 Dec - 27 Dec
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
"Was very happy"
Debbie 1-night trip
Posted 16 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

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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.