Hotels with Swimming Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with Swimming Pool

Tonight
Jan 1 - Jan 2
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Jan 2 - Jan 3
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Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

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 P5,762
P6,396 total
includes taxes & fees
Jan 25 - Jan 26
Comfort Inn & Suites Chestertown
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 P5,826
P6,661 total
includes taxes & fees
Jan 4 - Jan 5
The Lodge at Great Oak Landing
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, (326)
"Clean room, great staff, recommended. "
United States
Tom
The price is P6,356
P7,055 total
includes taxes & fees
Jan 11 - Jan 12
Fairfield Inn & Suites by Marriott Middletown
Indoor pool
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
2.5 star property
Edgewood
7.2 out of 10, Good, (1002)
"Room was great for the price, friendly staff"
United States
Gary
The price is P3,443
P3,856 total
includes taxes & fees
Jan 2 - Jan 3
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Lobby
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is P4,952
P5,497 total
includes taxes & fees
Jan 2 - Jan 3
Quality Inn Grasonville near Kent Island
Indoor pool
Holiday Inn Express & Suites Middletown by IHG

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, (653)
"Room was great the staff is so friendly every visit !!!!!"
United States
Dennis
The price is P5,423
P6,020 total
includes taxes & fees
Feb 1 - Feb 2
Holiday Inn Express & Suites Middletown by IHG
Seasonal outdoor pool
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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, (1003)
"Nice place"
United States
Maria
The price is P5,152
P5,770 total
includes taxes & fees
Jan 2 - Jan 3
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Indoor pool
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (868)
"Amazing stay"
United States
Katiana
The price is P5,598
P6,213 total
includes taxes & fees
Jan 7 - Jan 8
Hampton Inn Middletown
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is P7,002
P9,818 total
includes taxes & fees
Jan 4 - Jan 5
Kent Island Resort
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"It was an amazing stay!!!! Great staff! Amazing service! Food was great! Big up to the housekeeping team!!!! Nuff love!!!"
Rochelle 2-night trip
Posted 3 days ago
Hilton Garden Inn Baltimore/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: Hotel located near Baltimore Inner Harbor Marina. Provides 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. Historic Inns of Annapolis: Features complimentary wired internet access, an indoor pool, and free self parking. Best Western Plus Hotel & Conference Center: Offers a health club, an indoor pool, and a snack bar/deli.
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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