Find Hotels with a Pool in Chestertown, MD

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Our top choices for Chestertown hotels with a pool

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (872 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is NT$3,204
NT$3,557 total
includes taxes & fees
Mar 1 - Mar 2
Comfort Inn & Suites Chestertown

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 NT$3,420
NT$3,910 total
includes taxes & fees
Mar 10 - Mar 11
The Lodge at Great Oak Landing

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (343 reviews)
  • cleanliness
    Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.
The price is NT$3,136
NT$3,481 total
includes taxes & fees
Feb 15 - Feb 16
Fairfield Inn & Suites by Marriott Middletown

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Seasonal outdoor pool beckons with umbrella-shaded lounging spots perfect for refreshing dips amid Maryland's summer sun.
The price is NT$2,509
NT$2,810 total
includes taxes & fees
Mar 1 - Mar 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (619 reviews)
  • cleanliness
    Revitalizing dips await at this indoor pool sanctuary with attentive staff and plush amenities.
The price is NT$2,624
NT$2,938 total
includes taxes & fees
Feb 14 - Feb 15
Hampton Inn & Suites Baltimore/Aberdeen

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (132 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is NT$3,427
NT$4,892 total
includes taxes & fees
Feb 10 - Feb 11
Kent Island Resort

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, (1,001 reviews)
  • cleanliness
    Splash into summer at this hotel with a sparkling seasonal outdoor pool and tranquil landscaped grounds.
The price is NT$2,720
NT$3,046 total
includes taxes & fees
Feb 15 - Feb 16
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (875 reviews)
  • cleanliness
    Splash into serenity at this indoor pool sanctuary with a hot tub and fitness amenities for a complete wellness getaway.
The price is NT$3,012
NT$3,344 total
includes taxes & fees
Mar 9 - Mar 10
Hampton Inn 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, (660 reviews)
  • cleanliness
    Dive into year-round swimming at this hotel's inviting indoor pool, perfect for a refreshing Delaware getaway.
The price is NT$3,421
NT$3,798 total
includes taxes & fees
Feb 22 - Feb 23
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. 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: Offers complimentary wired internet access, an indoor pool, and free self parking. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Features buffet, an indoor pool, and free self parking. Hilton Garden Inn Baltimore/White Marsh: Offers a snack bar/deli, 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 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 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.

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