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Find Hotels with an Outdoor Pool in Chestertown, MD

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Top Chestertown Hotels with an Outdoor Pool

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
  • Pool loungers
8.6 out of 10, Excellent, (841)
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.
$102 nightly
The price is $113
Nov 11 - Nov 12
Total with taxes and fees
Comfort Inn & Suites Chestertown

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.
$113 nightly
The price is $126
Nov 9 - Nov 10
Total with taxes and fees
The Lodge at Great Oak Landing

First Floor Studio Apartment in Historic Chestertown

Chestertown
  • Outdoor pool
  • Hot tub
9.6 out of 10, Exceptional, (105)
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 center, and convenient laundry facilities.
$144 nightly
The price is $159
Nov 10 - Nov 11
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

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

3.0 star property
Bel Air
  • Pool umbrellas
8.8 out of 10, Excellent, (1009)
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.
$84 nightly
The price is $94
Nov 29 - Nov 30
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
  • Pool loungers
9.2 out of 10, Wonderful, (915)
Splashing in the seasonal outdoor pool reveals stunning Chesapeake Bay vistas, creating a waterfront oasis complete with sun loungers and umbrellas. Nearby adventures include hiking trails, kayaking, and sailing for the perfect coastal getaway.
$99 nightly
The price is $110
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG

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.
$68 nightly
The price is $75
Dec 9 - Dec 10
Total with taxes and fees
Quality Inn

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, (1001)
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.
$91 nightly
The price is $102
Nov 16 - Nov 17
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Kent Island Resort

3.5 star property
Stevensville
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (123)
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.
$186 nightly
The price is $203
Dec 1 - Dec 2
Total with taxes and fees
Kent Island Resort

The Inn at Chesapeake Bay Beach Club

4.0 star property
Stevensville
  • Full-service spa
9.4 out of 10, Exceptional, (425)
Seasonal outdoor pool beckons from May to September amid upscale amenities at this Chesapeake Bay hotel. Professional staff complement the experience with nearby dining options, complimentary bicycles, and rejuvenating spa treatments.
$207 nightly
The price is $230
Dec 1 - Dec 2
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club

Inn at Huntingfield Creek

3.5 star property
Rock Hall
  • Outdoor pool
  • Pool loungers
  • Full-service spa
10.0 out of 10, Exceptional, (56)
Poolside relaxation awaits at this waterfront bed and breakfast where sun loungers surround the inviting outdoor pool. After swimming, guests can enjoy spa massages, bicycle rentals, and hiking trails before returning to rooms with fireplaces and jetted tubs.
$144 nightly
The price is $160
Dec 1 - Dec 2
Total with taxes and fees
Inn at Huntingfield Creek
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.

Find out more about Chestertown

Discover top Chestertown attractions

In Chestertown, Maryland, travelers seeking relaxation will find a delightful blend of serene activities and charming locations. Start your day with a leisurely stroll along the Chester River, where the scenic waterfront invites you to unwind while enjoying views of historic architecture and boats gliding by. For a taste of local culture, visit the Kent County Arts Council, where you can explore rotating exhibitions that showcase regional artists and craftspeople. Families will appreciate a trip to the nearby Washington College, where picturesque grounds provide a perfect picnic spot or an opportunity to attend one of their community events. Afterward, indulge in a wine tasting at the nearby Crow Vineyard, where you can savor local wines while surrounded by lush vineyards. For accommodations, consider the hotels near the charming downtown area, where many feature inviting pools, allowing you to relax after a day of exploration. The combination of historical charm and modern comfort makes this area perfect for a family getaway, ensuring both relaxation and activities are just moments away.

Find the best hotels with an outdoor pool in Chestertown

For travelers seeking a refreshing retreat in Chestertown, Maryland, these hotels provide inviting outdoor pool amenities that enhance a leisurely stay. Enjoy the sun and water at these top picks!

The Lodge at Great Oak Landing

  • Why it's great for poolside lounging: The Lodge at Great Oak Landing is a fantastic choice for those looking to enjoy an outdoor pool experience amid the natural beauty of Chestertown. With a solid guest review rating of 7.4, this lodge offers a secured shared pool with sun loungers, perfect for relaxing or soaking up the sun after a day of adventures.
  • Other amenities: Guests can also take advantage of nearby private beach access for a day by the water, a fitness facility open 24 hours, and a marina view that adds to the scenic charm. Additional offerings include a playground for shared enjoyment, golf holes for enthusiasts, and various beach amenities like volleyball and sun loungers to enhance your outdoor experience.
  • Nearby attractions: Kinnairds Point Drive - 12.16 miles, Still Pond Station Park - 15.25 miles

Top Chestertown Hotel Reviews

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