Search Hotels with Pool in Chestertown

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Check availability on Chestertown Hotels with Pool

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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
The price is ฿3,133
฿3,478 total
includes taxes & fees
25 Jan - 26 Jan 2026
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
The price is ฿3,079
฿3,521 total
includes taxes & fees
28 Dec - 29 Dec
The Lodge at Great Oak Landing
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
The price is ฿2,551
฿2,857 total
includes taxes & fees
27 Dec - 28 Dec
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, (325)
"Clean room, great staff, recommended. "
United States
Tom
The price is ฿3,356
฿3,726 total
includes taxes & fees
30 Dec - 31 Dec
Fairfield Inn & Suites by Marriott Middletown
Free daily self-service breakfast
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1001)
"Great stay"
United States
Edward
The price is ฿2,113
฿2,346 total
includes taxes & fees
25 Jan - 26 Jan 2026
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)
"Amazing stay"
United States
Katiana
The price is ฿2,959
฿3,284 total
includes taxes & fees
6 Jan - 7 Jan 2026
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
The price is ฿2,579
฿2,889 total
includes taxes & fees
31 Dec - 1 Jan 2026
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)
"Ty"
United States
Mary
The price is ฿2,217
฿2,483 total
includes taxes & fees
24 Jan - 25 Jan 2026
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, (605)
"very pet friendly!!"
United States
larry
The price is ฿3,052
฿3,418 total
includes taxes & fees
9 Jan - 10 Jan 2026
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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Yes and yes"
MARY ANN 1-night trip
Posted 5 days ago
Hampton Inn Baltimore/Glen Burnie

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. 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 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.
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 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.