Chestertown Hotel Guide - Hotels with Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with Pool

Tonight
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Chestertown Hotels with Pool

Room, 1 King Bed with Sofa bed, Marina View
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
  • Pool loungers
  • Private beach access
8.0 out of 10, Very good, (76)
Splash into summer fun at the seasonal outdoor pool, complete with loungers and umbrellas for all-day relaxation. Beyond the water, this lodge offers a private beach, 9-hole golf course, and delicious dining at Fairlee's restaurant.
The price is €98
includes taxes & fees
11 Dec - 12 Dec
The Lodge at Great Oak Landing
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
  • Outdoor pool
  • Hot tub
9.6 out of 10, Exceptional, (107)
Sparkling waters of the private pool invite guests to unwind after exploring charming Chestertown or biking rural roads. Beyond aquatic pleasures, this spotless property features a hot tub, fitness centre, and convenient laundry facilities.
The price is €141
includes taxes & fees
1 Dec - 2 Dec
First Floor Studio Apartment in Historic Chestertown
Free daily continental breakfast
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

2.5 star property
Edgewood
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Gym
9.0 out of 10, Wonderful, (546)
Sparkling waters beckon at this conveniently located hotel, offering a refreshing swimming oasis alongside 24-hour fitness facilities. Spotless accommodation and complimentary continental breakfast complete a rejuvenating stay near Interstate 95.
The price is €76
includes taxes & fees
4 Dec - 5 Dec
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Indoor pool
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
  • Indoor pool
9.4 out of 10, Exceptional, (1011)
Swimmers splash into the warmth of a pristine indoor pool, accessible from early morning until evening. Beyond aquatic pleasures, guests enjoy a comprehensive health club, 24-hour service, and peaceful accommodation praised for exceptional cleanliness.
The price is €79
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn & Suites Edgewood/Aberdeen-South
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
  • Indoor pool
9.0 out of 10, Wonderful, (595)
Splash into holiday mode at the pristine indoor swimming pool after enjoying the complimentary breakfast buffet. Clean, comfortable accommodation and exceptionally friendly staff create a peaceful retreat complete with fitness centre and tennis courts.
The price is €87
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Indoor pool, pool loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (666)
Pool loungers invite guests to unwind beside the tranquil indoor pool after exploring nearby trails and beaches. With stunning waterfront vistas, delicious breakfast options, and spacious, comfortable rooms, this hotel offers a serene island retreat.
The price is €111
includes taxes & fees
1 Dec - 2 Dec
Hyatt Place Kent Narrows & Marina
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (127)
Sparkling waters welcome swimmers to this seasonal retreat where comfortable loungers await beneath shade umbrellas. Beyond the refreshing pool, adventures beckon with complimentary bicycles, kayaking, and fishing along the picturesque Chesapeake Bay.
The price is €136
includes taxes & fees
7 Dec - 8 Dec
Kent Island Resort
Indoor pool
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
  • Indoor pool
9.2 out of 10, Wonderful, (307)
Swimming enthusiasts cherish the pristine indoor pool, a centrepiece amenity complemented by exceptional staff service and continental breakfast. Situated near restaurants and attractions, this well-maintained Fairfield Inn & Suites delivers comfort in a convenient location.
The price is €101
includes taxes & fees
28 Dec - 29 Dec
Fairfield Inn & Suites by Marriott Middletown
Seasonal outdoor pool
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
Aberdeen
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
9.0 out of 10, Wonderful, (1013)
Sparkling clean waters invite summer dips in the seasonal outdoor pool open from May through August. After swimming, guests recharge with a complimentary breakfast buffet before exploring Aberdeen's convenient dining options and attractions.
The price is €89
includes taxes & fees
30 Nov - 1 Dec
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Amazing staff. Clean room."
Cindy 1-night trip
Posted 1 day ago
Best Western Plus Hotel & Conference Center

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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. Features 2 bars, a seasonal outdoor pool and spa services. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool and free self parking. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Provides complimentary high-speed (wired) Internet access, 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, Chestertown Historic District and Rolphs Wharf Marina 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.