Chestertown Hotel Guide - Hotels with Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with Pool

Tonight
27 Feb - 28 Feb
Tomorrow
28 Feb - 1 Mar
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 €105
includes taxes & fees
23 Mar - 24 Mar
The Lodge at Great Oak Landing
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
  • cleanliness
    Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
The price is €138
includes taxes & fees
2 Mar - 3 Mar
First Floor Studio Apartment in Historic Chestertown
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 €95
includes taxes & fees
8 Mar - 9 Mar
Comfort Inn & Suites Chestertown
Outdoor pool, a heated pool

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
  • cleanliness
    Waterfront paradise beckons with a heated outdoor pool, private aquatic oasis, and scenic creek views in tranquil Annapolis.
The price is €345
includes taxes & fees
1 Mar - 2 Mar
Waterfront Oasis of Annapolis Star
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 €88
includes taxes & fees
1 Mar - 2 Mar
Best Western Kent Narrows Inn
Indoor pool

Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (437 reviews)
  • cleanliness
    Experience the refreshing escape of an indoor pool in Aberdeen, perfect for year-round relaxation and fun after your adventures.
The price is €102
includes taxes & fees
6 Mar - 7 Mar
Holiday Inn Express Aberdeen by IHG
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
Indoor pool

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (640 reviews)
  • cleanliness
    Plunge into tranquil waters at this hotel's refreshing indoor pool for a serene aquatic escape.
The price is €93
includes taxes & fees
6 Mar - 7 Mar
Hilton Garden Inn Aberdeen
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (876 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is €79
includes taxes & fees
8 Mar - 9 Mar
Quality Inn Grasonville near Kent Island
Indoor pool

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.2 out of 10, Wonderful, (106 reviews)
  • cleanliness
    Refreshing indoor pool escape lets swimmers splash any season at this Aberdeen retreat.
The price is €125
includes taxes & fees
28 Feb - 1 Mar
TownePlace Suites by Marriott Edgewood Aberdeen
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Very clean and stay was better than expected."
Daniel 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.