Search Hotels with Pool in Chestertown

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Check availability on Chestertown Hotels with Pool

Tonight
28 Apr - 29 Apr
Tomorrow
29 Apr - 30 Apr
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

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, (80 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
The price is Rp1.858.788
Rp2.125.152 total
includes taxes & fees
30 Apr - 1 May
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, (908 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is Rp2.081.843
Rp2.310.846 total
includes taxes & fees
21 May - 22 May
Comfort Inn & Suites Chestertown
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, (377 reviews)
  • cleanliness
    Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.
The price is Rp2.013.687
Rp2.235.193 total
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites by Marriott Middletown
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 Rp1.857.411
Rp2.061.726 total
includes taxes & fees
5 May - 6 May
Best Western Kent Narrows Inn
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is Rp2.512.099
Rp3.367.561 total
includes taxes & fees
30 Apr - 1 May
Kent Island Resort
Outdoor pool, pool loungers

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is Rp3.105.381
Rp3.447.019 total
includes taxes & fees
6 May - 7 May
Inn at Huntingfield Creek
Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,001 reviews)
  • cleanliness
    Dip into poolside bliss at this hotel with a sun-soaked outdoor pool and modern fitness centre nearby.
The price is Rp1.405.794
Rp1.560.431 total
includes taxes & fees
6 May - 7 May
Quality Inn Smyrna
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)
  • cleanliness
    Splash into summer at this hotel with a sparkling seasonal outdoor pool and tranquil landscaped grounds.
The price is Rp1.521.452
Rp1.704.026 total
includes taxes & fees
6 May - 7 May
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Indoor pool, outdoor pool

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
  • cleanliness
    Splash into waterfront bliss with indoor and outdoor pools at this log cabin retreat.
The price is Rp6.020.709
Rp7.294.135 total
includes taxes & fees
30 Apr - 1 May
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Very good "
Rashi 1-night trip
Posted 2 hours ago
Hilton Garden Inn Baltimore/White Marsh

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. The Lodge at Great Oak Landing: Offers 3 bars, 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. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool and free self parking. Pendry Baltimore: Provides complimentary high-speed (wired) Internet access, an indoor pool and free self parking.
What is there to see and do in Chestertown?
Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Rolphs Wharf Marina, Historical Society of Kent County Maryland 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.