Find Hotels with a Pool in Chestertown, MD

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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
8.0 out of 10, Very Good, (81 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
The price is AED 464
AED 531 total
includes taxes & fees
27 May - 28 May
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, (111 reviews)
  • cleanliness
    Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
The price is AED 364
AED 583 total
includes taxes & fees
18 May - 19 May
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, (911 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is AED 396
AED 439 total
includes taxes & fees
14 Jun - 15 Jun
Comfort Inn & Suites Chestertown

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,002 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is AED 423
AED 469 total
includes taxes & fees
27 May - 28 May
Best Western Kent Narrows Inn

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 AED 654
AED 726 total
includes taxes & fees
17 May - 18 May
Inn at Huntingfield Creek

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 center nearby.
The price is AED 302
AED 336 total
includes taxes & fees
26 May - 27 May
Quality Inn Smyrna

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 AED 1,285
AED 1,557 total
includes taxes & fees
21 May - 22 May
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (653 reviews)
  • cleanliness
    Plunge into tranquil waters at this hotel's refreshing indoor pool for a serene aquatic escape.
The price is AED 389
AED 435 total
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Aberdeen

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (386 reviews)
  • cleanliness
    Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.
The price is AED 382
AED 424 total
includes taxes & fees
31 May - 1 Jun
Fairfield Inn & Suites by Marriott Middletown

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (648 reviews)
  • cleanliness
    Revitalizing dips await at this indoor pool sanctuary with attentive staff and plush amenities.
The price is AED 346
AED 388 total
includes taxes & fees
26 May - 27 May
Hampton Inn & Suites Baltimore/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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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. Red Roof Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor pool, and free self parking. The Lodge at Great Oak Landing: Hotel located near Baltimore Inner Harbor Marina. Provides 2 bars, a seasonal outdoor pool, and spa services. Blue Heron Farm Waterfront Chalet: Features complimentary wired internet access, an indoor pool, and free self parking. Historic Inns of Annapolis: 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 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 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.