Search Hotels with Swimming Pool in Chestertown

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Check availability on Chestertown Hotels with Swimming Pool

Our top choices for Chestertown hotels with a pool

Aerial view

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is ₹9,957
₹11,384 total
includes taxes & fees
17 Mar - 18 Mar
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, (885 reviews)
"Staying is peaceful and the rooms clean."
United States
Robert
The price is ₹9,635
₹10,695 total
includes taxes & fees
19 Mar - 20 Mar
Comfort Inn & Suites Chestertown
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,006 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is ₹8,666
₹9,619 total
includes taxes & fees
17 Mar - 18 Mar
Best Western Kent Narrows Inn
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (972 reviews)
"Check-in was great! The young man at the desk was so friendly and helpful!! Room was clean and beds were clean and comfortable!"
United States
Kelley
The price is ₹9,957
₹11,052 total
includes taxes & fees
23 Mar - 24 Mar
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (355 reviews)
"Consistently a good stay here with helpful staff and comfortable rooms. "
United States
Mary
The price is ₹9,127
₹10,131 total
includes taxes & fees
22 Mar - 23 Mar
Fairfield Inn & Suites by Marriott Middletown
Indoor pool, open 5 AM to 11 PM, pool loungers

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is ₹10,509
₹11,664 total
includes taxes & fees
18 Mar - 19 Mar
Hilton Garden Inn Kent Island Marina
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (880 reviews)
"Staff was friendly and helpful and allowed me to check in early"
United States
Chad
The price is ₹8,619
₹9,568 total
includes taxes & fees
17 Mar - 18 Mar
Quality Inn Grasonville near Kent Island
Outdoor pool, pool loungers

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (61 reviews)
"Breakfast was outstanding!! Lovely inn, I’ll definitely keep it in mind for future travels."
United States
Isobel
Inn at Huntingfield Creek
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, (1,001 reviews)
"Clean room, near shopping & dining, & complimentary breakfast buffet! "
United States
Chanel
The price is ₹7,993
₹8,953 total
includes taxes & fees
30 Mar - 31 Mar
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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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Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub

Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Room and all surrounding areas were very clean. The staff was so kind and so friendly. It is in an amazing location and some very good choices for food right in the shopping plaza. "
Linda 2-night trip
Posted 7 hours 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. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool and spa services. Historic Inns of Annapolis: Features complimentary high-speed (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. Hampton Inn Baltimore/Glen Burnie: Features a snack bar/deli, a seasonal outdoor pool and buffet.
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, Garfield Center for the Arts at the Prince Theater 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.