Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

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, (75)
"Very nice rooms, "
United States
Stephania
The price is SAR 371
SAR 424 total
includes taxes & fees
23 Nov - 24 Nov
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, (848)
"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 SAR 383
SAR 425 total
includes taxes & fees
23 Nov - 24 Nov
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, (106)
"Amazing and neat and very private "
United States
Alexander M.
The price is SAR 371
SAR 596 total
includes taxes & fees
1 Dec - 2 Dec
First Floor Studio Apartment in Historic Chestertown
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, (305)
"Great overall experience "
United States
Clement
The price is SAR 405
SAR 450 total
includes taxes & fees
24 Nov - 25 Nov
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
9.4 out of 10, Exceptional, (1005)
"Would stay again"
United States
Dena
The price is SAR 306
SAR 343 total
includes taxes & fees
30 Nov - 1 Dec
Hampton Inn & Suites Edgewood/Aberdeen-South
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (591)
"Wonderful room and location "
United States
Caren
The price is SAR 339
SAR 380 total
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Indoor pool, open 5 AM to 11 PM, sun loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1000)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is SAR 358
SAR 397 total
includes taxes & fees
26 Nov - 27 Nov
Hilton Garden Inn Kent Island Marina
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, (425)
"Kid friendly for sure! The room and hotel is clean and comfy, no complaints! Chlorine smell a bit strong in pool area but it didn’t bother me. We missed breakfast so not sure about that but everything else was great!"
United States
Gabrielle
The price is SAR 428
SAR 479 total
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn Express Aberdeen by IHG
Indoor pool
TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen

3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (90)
"Breakfast was good."
United States
Romelle
The price is SAR 379
SAR 424 total
includes taxes & fees
7 Dec - 8 Dec
TownePlace Suites by Marriott Edgewood Aberdeen
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
The price is SAR 255
SAR 283 total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Good location. Very pricey but not much competition "
jason 2-night trip
Posted 3 days ago
Comfort Inn & Suites Chestertown

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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. Offers 2 bars, a seasonal outdoor pool, and spa services. Historic Inns of Annapolis: Features complimentary wired internet access, an indoor pool, and free self parking. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Provides 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, 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.