Hotels with Swimming Pools in Chestertown

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Check availability on Chestertown Hotels with Swimming Pools

Tonight
25 Feb - 26 Feb
Tomorrow
26 Feb - 27 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

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)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
The price is S$156
includes taxes & fees
26 Mar - 27 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, (879 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is S$142
includes taxes & fees
8 Mar - 9 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, (1,000 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is S$132
includes taxes & fees
15 Mar - 16 Mar
Best Western Kent Narrows Inn
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, (574 reviews)
  • cleanliness
    Splash into a refreshing escape at this Edgewood hotel, where pool relaxation awaits after adventure-filled days.
The price is S$122
includes taxes & fees
27 Feb - 28 Feb
Holiday Inn Express Edgewood-Aberdeen-Bel Air 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, (350 reviews)
  • cleanliness
    Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.
The price is S$136
includes taxes & fees
8 Mar - 9 Mar
Fairfield Inn & Suites by Marriott Middletown
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)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
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, (875 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is S$118
includes taxes & fees
8 Mar - 9 Mar
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, (639 reviews)
  • cleanliness
    Plunge into tranquil waters at this hotel's refreshing indoor pool for a serene aquatic escape.
The price is S$131
includes taxes & fees
6 Mar - 7 Mar
Hilton Garden Inn 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, (349 reviews)
  • cleanliness
    Indoor pool retreat offers relaxing swims with modern amenities and helpful staff around the clock.
The price is S$138
includes taxes & fees
22 Mar - 23 Mar
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

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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Room was clean and quiet… will definitely return "
Kelly 1-night trip
Posted 1 day ago
Best Western Plus Hotel & Conference Center

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. Provides 2 bars, a seasonal outdoor pool and spa services. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Features buffet, an indoor pool and free self parking. Best Western Plus Hotel & Conference Center: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Historic Inns of Annapolis: Hotel located near Johns Hopkins Hospital. Offers a snack bar/deli, an indoor 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.

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