Chestertown Hotels with Swimming Pool

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Check availability on Chestertown Hotels with Swimming Pools

Tonight
1 Apr - 2 Apr
Tomorrow
2 Apr - 3 Apr
This weekend
3 Apr - 5 Apr
Next weekend
10 Apr - 12 Apr

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 RM435
RM497 total
includes taxes & fees
9 Apr - 10 Apr
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, (893 reviews)
"Best place to stay always "
United States
Robert
The price is RM496
RM550 total
includes taxes & fees
3 May - 4 May
Comfort Inn & Suites Chestertown
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (134 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is RM522
RM701 total
includes taxes & fees
8 Apr - 9 Apr
Kent Island Resort
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,001 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is RM433
RM480 total
includes taxes & fees
6 Apr - 7 Apr
Best Western Kent Narrows Inn
Outdoor pool, pool loungers

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is RM567
RM630 total
includes taxes & fees
12 Apr - 13 Apr
Inn at Huntingfield Creek
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (886 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is RM394
RM437 total
includes taxes & fees
9 Apr - 10 Apr
Quality Inn Grasonville near Kent Island
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, (1,002 reviews)
"Near $95 and good place to stay"
United States
Thandavarayan
The price is RM356
RM399 total
includes taxes & fees
15 Apr - 16 Apr
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Indoor pool

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (325 reviews)
"The staff was lovely and so accommodating. Definitely the best part of our stay."
United States
Maritza
The price is RM441
RM494 total
includes taxes & fees
19 Apr - 20 Apr
Fairfield Inn & Suites by Marriott Aberdeen
Indoor pool

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, (358 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is RM409
RM459 total
includes taxes & fees
3 May - 4 May
Home2 Suites by Hilton Baltimore / 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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Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent
"Clean, spacious room. Quiet location. Decent breakfast. "
Melanie 1-night trip
Posted 7 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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. Historic Inns of Annapolis: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool and spa services. Hampton Inn Baltimore/Glen Burnie: 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: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Pendry Baltimore: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access.
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, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater 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.

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