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Chestertown Hotel with Pool

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Check availability on Chestertown Hotel with Pool

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for Chestertown hotels with a pool

Aerial view

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (88 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
The price is HK$1,037
HK$1,186 total
includes taxes & fees
29 Jun - 30 Jun
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, (926 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is HK$809
HK$898 total
includes taxes & fees
19 Jul - 20 Jul
Comfort Inn & Suites Chestertown
Outdoor pool

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (113 reviews)
  • cleanliness
    Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
The price is HK$776
HK$1,245 total
includes taxes & fees
8 Jul - 9 Jul
First Floor Studio Apartment in Historic Chestertown
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, pool loungers

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (147 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is HK$1,233
HK$1,635 total
includes taxes & fees
1 Jul - 2 Jul
Kent Island Resort
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (927 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is HK$784
HK$870 total
includes taxes & fees
8 Jul - 9 Jul
Quality Inn Grasonville near Kent Island
Indoor pool

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (662 reviews)
  • cleanliness
    Plunge into tranquil waters at this hotel's refreshing indoor pool for a serene aquatic escape.
The price is HK$804
HK$900 total
includes taxes & fees
3 Jul - 4 Jul
Hilton Garden Inn Aberdeen
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is HK$982
HK$1,089 total
includes taxes & fees
8 Jul - 9 Jul
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, (65 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is HK$1,396
HK$1,550 total
includes taxes & fees
8 Jul - 9 Jul
Inn at Huntingfield Creek
Free daily continental breakfast

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, (611 reviews)
  • cleanliness
    Splash into a refreshing escape at this Edgewood hotel, where pool relaxation awaits after adventure-filled days.
The price is HK$729
HK$817 total
includes taxes & fees
1 Jul - 2 Jul
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
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, (1,000 reviews)
  • cleanliness
    Splash into summer at this hotel with a sparkling seasonal outdoor pool and tranquil landscaped grounds.
The price is HK$734
HK$822 total
includes taxes & fees
29 Jun - 30 Jun
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 & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"It was family friendly and very affordable"
Nena 1-night trip
Posted 10 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South

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 free self parking, a seasonal outdoor pool and sunloungers. 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: Hotel located near Johns Hopkins Hospital. Features buffet, an indoor pool and free self parking. Annapolis Waterfront Hotel, Autograph Collection: Offers free self parking, 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 Chestertown Historic District, Rolphs Wharf Marina and Historical Society of Kent County Maryland 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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