Find Hotels with an Outdoor Pool in Eastern Shore, MD

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Top Eastern Shore Hotels with an Outdoor Pool

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
9.2 out of 10, Wonderful, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
$79 nightly
The price is $88
Dec 18 - Dec 19
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG

Grand Hotel Ocean City Oceanfront

3.0 star property
Downtown Ocean City
9.0 out of 10, Wonderful, (3337)
"Great view, good stay."
United States
Emre
$68 nightly
The price is $76
Dec 21 - Dec 22
Total with taxes and fees
Grand Hotel Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront

4.0 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1003)
"The room was clean,the staff was friendly and I enjoyed my stay."
United States
Kelvin
$77 nightly
The price is $86
Dec 11 - Dec 12
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront

Hyatt Regency Chesapeake Bay

4.0 star property
Cambridge
8.8 out of 10, Excellent, (1000)
"Very courteous staff."
United States
Joseph
$201 nightly
The price is $229
Dec 15 - Dec 16
Total with taxes and fees
Hyatt Regency Chesapeake Bay

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (858)
"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. "
United States
Santa
$102 nightly
The price is $113
Dec 25 - Dec 26
Total with taxes and fees
Comfort Inn & Suites Chestertown

Park Place Hotel

3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (1045)
"Excellent spot, clean, amazing views. "
United States
Sacra
$75 nightly
The price is $83
Jan 4 - Jan 5, 2026
Total with taxes and fees
Park Place Hotel

Hyatt Place Ocean City / Oceanfront

3.0 star property
Downtown Ocean City
9.0 out of 10, Wonderful, (1591)
"Room was very clean, staff were the best.would definitely recommend staying there."
United States
Gary
$80 nightly
The price is $89
Dec 14 - Dec 15
Total with taxes and fees
Hyatt Place Ocean City / Oceanfront

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
9.4 out of 10, Exceptional, (359)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
$100 nightly
The price is $110
Dec 7 - Dec 8
Total with taxes and fees
Knapps Narrows Marina & Inn

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

2.5 star property
Midtown Ocean City
8.8 out of 10, Excellent, (1002)
"Good hotel overall."
United States
Niama
$55 nightly
The price is $61
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
$163 nightly
The price is $177
Dec 7 - Dec 8
Total with taxes and fees
Kent Island Resort
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 Eastern Shore

Discover top Eastern Shore attractions

The Eastern Shore of the United States offers a delightful mix of relaxation and adventure, perfect for looking for a tranquil getaway. Begin your exploration at Assateague Island National Seashore, where wild ponies roam free along pristine beaches, allowing for serene walks and unforgettable family photos. Then, head to the charming town of St. Michaels, known for its quaint shops and waterfront dining, where you can relish fresh seafood while enjoying picturesque views of the Chesapeake Bay. For a touch of history, visit the Chesapeake Bay Maritime Museum, which offers engaging exhibits that the whole family can enjoy, making it both educational and leisurely. The area is also dotted with beautiful parks and nature reserves perfect for picnicking or leisurely bike rides, such as the Eastern Shore’s Blackwater National Wildlife Refuge, renowned for its scenic landscapes and birdwatching opportunities. After a day of exploration, unwind at one of the many hotels featuring stunning pools, like the Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina, where you can relax poolside while the kids splash around or indulge in a spa treatment. Staying in the St. Michaels area provides a wonderful home base, with easy access to various attractions and a welcoming atmosphere, ensuring that every moment of your stay is filled with comfort and enjoyment.

Top Eastern Shore Hotel Reviews

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