Chestertown Hotel with Pool

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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.
"beautiful pool…."
United States
Stephen
The price is HK$994
HK$1,137 total
includes taxes & fees
18 May - 19 May
The Lodge at Great Oak Landing
Outdoor pool

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.
"We did not get a chance to use the pool, but it looked very inviting."
United States
Christine G.
The price is HK$775
HK$1,244 total
includes taxes & fees
12 May - 13 May
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, (909 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
"Best of all the pool has been scrubbed sparkling clean up and running beautifully...that was a real happy surprise."
United States
Veronica
The price is HK$952
HK$1,057 total
includes taxes & fees
7 Jun - 8 Jun
Comfort Inn & Suites Chestertown
Seasonal outdoor pool

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (905 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
"Very clean room dirty pool staff was great"
United States
Lisa
The price is HK$832
HK$923 total
includes taxes & fees
28 May - 29 May
Quality Inn Grasonville near Kent Island
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 pool was refreshing and we took advantage of that on 2 hot days."
United States
Lynn
The price is HK$1,413
HK$1,568 total
includes taxes & fees
17 May - 18 May
Inn at Huntingfield Creek
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.
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is HK$2,739
HK$3,318 total
includes taxes & fees
14 May - 15 May
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,006 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
"Clean room, hot water, huge breakfast, indoor pool, definitely an inexpensive nice place to stay just over the Bay on Na Shore, walking distance to Kent Narrows Airport"
United States
Tasha
The price is HK$901
HK$1,000 total
includes taxes & fees
25 May - 26 May
Best Western Kent Narrows Inn
Indoor pool

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 pool was absolutely packed"
United States
Rachel
The price is HK$828
HK$928 total
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Aberdeen
Indoor pool

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (643 reviews)
  • cleanliness
    Revitalising dips await at this indoor pool sanctuary with attentive staff and plush amenities.
"Great breakfast and pool time."
United States
Eric
The price is HK$738
HK$827 total
includes taxes & fees
3 Jun - 4 Jun
Hampton Inn & Suites Baltimore/Aberdeen
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, (383 reviews)
  • cleanliness
    Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.
"Small pool."
United States
Nadine
The price is HK$932
HK$1,034 total
includes taxes & fees
31 May - 1 Jun
Fairfield Inn & Suites by Marriott Middletown
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

6/10 Okay
"The finer cleaning details aren't paid attention to in this hotel. The desk in the queen suite was dirty and stained, the sink was clogged in the kitchenette. The pool floor is dirty. Breakfast is not impressive, some days we decided to go and pay for food elsewhere."
Kimberlee 3-night trip
Posted 6 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South

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. 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 high-speed (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 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.

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