Hotels with Swimming Pool in Chestertown, Maryland

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Hotels with Swimming Pool

Top Chestertown Hotels with Swimming Pool

1 bedroom, free WiFi, bed sheets
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, (75)
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 P5,846
P6,684 total
includes taxes & fees
Nov 17 - Nov 18
The Lodge at Great Oak Landing
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
  • Pool loungers
8.6 out of 10, Excellent, (847)
Poolside relaxation awaits with sun loungers and umbrellas surrounding the seasonal outdoor oasis. After swimming, guests can enjoy the fitness center, savor a free full breakfast, or explore nearby Washington College and River Arts.
The price is P6,024
P6,686 total
includes taxes & fees
Nov 19 - Nov 20
Comfort Inn & Suites Chestertown
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, (1002)
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 accommodations praised for exceptional cleanliness.
The price is P4,819
P5,397 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn & Suites Edgewood/Aberdeen-South
Indoor pool
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
Middletown
  • Indoor pool
9.2 out of 10, Wonderful, (639)
Splash into the pristine indoor pool, accessible from morning to night, after exploring nearby Dutch Country Farmers Market. Immaculate rooms with pillow menus await, complemented by a complimentary breakfast buffet that guests consistently praise as delicious and varied.
The price is P6,850
P7,604 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express & Suites Middletown by IHG
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, (304)
Swimming enthusiasts cherish the pristine indoor pool, a centerpiece 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 P6,378
P7,080 total
includes taxes & fees
Nov 23 - Nov 24
Fairfield Inn & Suites by Marriott Middletown
Indoor pool, open 5 AM to 11 PM, sun loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1000)
Waterfront serenity awaits at the indoor pool, complete with comfortable sun loungers and extended hours from 5 AM to 11 PM. Steps from the marina, this hotel combines aquatic pleasure with scenic beauty and a modern fitness center.
The price is P6,009
P6,670 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Kent Island Marina
Free daily self-serve breakfast
Quality Inn

Quality Inn

2.5 star property
Smyrna
  • Outdoor pool
7.6 out of 10, Good, (1001)
Swimming enthusiasts splash into the inviting outdoor pool, a refreshing centerpiece after workouts in the fitness center. Friendly staff ensure exceptional service throughout the hotel, complemented by comfortable, clean accommodations just steps from local dining options.
The price is P4,016
P4,457 total
includes taxes & fees
Dec 17 - Dec 18
Quality Inn
Seasonal outdoor pool, pool umbrellas
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

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

3.0 star property
Bel Air
  • Pool umbrellas
8.8 out of 10, Excellent, (1002)
Seasonal outdoor umbrellas dot the crystal-clear pool, creating idyllic shaded retreats for sun-soaked afternoons. Guests appreciate immaculately clean rooms with premium bedding after invigorating fitness center workouts at this eco-certified Maryland hotel.
The price is P5,262
P5,893 total
includes taxes & fees
Nov 23 - Nov 24
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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, (590)
Splash into vacation mode at the pristine indoor swimming pool after enjoying the complimentary breakfast buffet. Clean, comfortable accommodations and exceptionally friendly staff create a peaceful retreat complete with fitness center and tennis courts.
The price is P5,339
P5,979 total
includes taxes & fees
Dec 8 - Dec 9
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.
View all properties

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
Santa 5-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown

Explore a world of travel with Expedia

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. Offers 2 bars, a seasonal outdoor pool, and spa services. Historic Inns of Annapolis: Features complimentary wired internet access, an indoor pool, and free self parking. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Provides buffet, 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 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.