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Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Tonight
Nov 8 - Nov 9
Tomorrow
Nov 9 - Nov 10
Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23

Top Chestertown Hotels with a Pool

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, (842)
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 NT$3,156
NT$3,503 total
includes taxes & fees
Nov 18 - Nov 19
Comfort Inn & Suites Chestertown
Room, 1 King Bed with Sofa bed, Marina View | 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, (74)
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 NT$3,063
NT$3,502 total
includes taxes & fees
Nov 18 - Nov 19
The Lodge at Great Oak Landing
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, (1001)
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 NT$2,529
NT$2,832 total
includes taxes & fees
Nov 17 - Nov 18
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (300)
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 NT$3,341
NT$3,709 total
includes taxes & fees
Nov 19 - Nov 20
Fairfield Inn & Suites by Marriott Middletown
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, (1003)
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 NT$2,608
NT$2,920 total
includes taxes & fees
Nov 29 - Nov 30
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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, (638)
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 NT$3,223
NT$3,577 total
includes taxes & fees
Dec 5 - Dec 6
Holiday Inn Express & Suites Middletown by IHG
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 NT$2,107
NT$2,339 total
includes taxes & fees
Dec 9 - Dec 10
Quality Inn
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, (588)
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 NT$2,801
NT$3,137 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn & Suites Baltimore/Aberdeen
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
  • Indoor pool
  • Hot tub
8.0 out of 10, Very Good, (1003)
Sparkling waters await in the pristine indoor swimming pool, complemented by a rejuvenating hot tub and sauna. Active travelers appreciate the nearby hiking trails while enjoying spotless accommodations with 49-inch TVs and refrigerators.
The price is NT$2,847
NT$3,160 total
includes taxes & fees
Nov 16 - Nov 17
Best Western Kent Narrows Inn
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Great breakfast, good location, clean."
william 3-night trip
Posted 4 days ago
Fairfield Inn & Suites by Marriott White Marsh

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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. 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 Baltimore Cruise Terminal. Provides buffet, an indoor pool, and free self parking.
What is there to see and do in Chestertown?
Surround yourself with nature at Chesapeake Bay and Chestertown Dog Park. Discover sights such as Historical Society of Kent County Maryland, Rolphs Wharf Marina, 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.