Find Hotels with a Pool in Chestertown, MD from CA $124

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Hotels with a Pool

Our top choices for Chestertown hotels with a pool

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 CA $149
CA $171 total
includes taxes & fees
Apr 15 - Apr 16
The Lodge at Great Oak Landing

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 CA $137
CA $220 total
includes taxes & fees
Apr 15 - Apr 16
First Floor Studio Apartment in Historic Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (898 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is CA $170
CA $188 total
includes taxes & fees
May 3 - May 4
Comfort Inn & Suites Chestertown

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 CA $165
CA $224 total
includes taxes & fees
Apr 14 - Apr 15
Kent Island Resort

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,008 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is CA $137
CA $153 total
includes taxes & fees
Apr 26 - Apr 27
Best Western Kent Narrows Inn

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 CA $112
CA $124 total
includes taxes & fees
Apr 19 - Apr 20
Quality Inn Smyrna

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is CA $194
CA $215 total
includes taxes & fees
Apr 18 - Apr 19
Inn at Huntingfield Creek

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 CA $570
CA $677 total
includes taxes & fees
Apr 14 - Apr 15
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (369 reviews)
  • cleanliness
    Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.
The price is CA $144
CA $160 total
includes taxes & fees
Apr 26 - Apr 27
Fairfield Inn & Suites by Marriott Middletown

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (675 reviews)
  • cleanliness
    Dive into year-round swimming at this hotel's inviting indoor pool, perfect for a refreshing Delaware getaway.
The price is CA $140
CA $155 total
includes taxes & fees
Apr 19 - Apr 20
Holiday Inn Express & Suites Middletown by IHG
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.

Choose what matters most at hotels with a pool in Chestertown

Top Chestertown Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Chestertown?
Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool, and free self parking. Blue Heron Farm Waterfront Chalet: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool, and spa services. Historic Inns of Annapolis: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool, and free self parking. Hampton Inn Baltimore/Glen Burnie: Features complimentary wired internet access, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: 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 Garfield Center for the Arts at the Prince Theater, 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 offers an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August, or June when the average temperature is 74°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 39°F.

Explore a world of travel with Expedia