Find Hotels with a Pool in Eastern Shore, MD

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Top Eastern Shore Hotels with a Pool

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
  • Pool loungers
9.2 out of 10, Wonderful, (914)
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

DoubleTree by Hilton Ocean City Oceanfront

4.0 star property
Midtown Ocean City
  • 2 outdoor pools
  • Indoor pool
  • Poolside bar
  • Pool loungers
  • On the beach
9.0 out of 10, Wonderful, (1001)
Sparkling indoor and outdoor pools invite swimmers year-round, with sun loungers perfectly positioned for ocean gazing. After cooling off, guests savor handcrafted drinks at the poolside bar while planning beach adventures just steps away.
$80 nightly
The price is $89
Dec 1 - Dec 2
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront

3.0 star property
Midtown Ocean City
  • Indoor pool
  • Pool loungers
  • On the beach
9.0 out of 10, Wonderful, (1055)
Sparkling waters beckon year-round at the indoor pool, complete with plush loungers and adjacent fitness center featuring a Peloton bike. After swimming, guests savor ocean views at Solstice Bar & Grill before joining morning beach yoga classes.
$63 nightly
The price is $70
Nov 23 - Nov 24
Total with taxes and fees
Hilton Garden Inn Ocean City Oceanfront

Hyatt Place Ocean City / Oceanfront

3.0 star property
Downtown Ocean City
  • Indoor pool
  • Poolside bar
  • Pool loungers
  • On the beach
9.0 out of 10, Wonderful, (1579)
Swim year-round at the indoor pool or summer away at the seasonal outdoor oasis, complete with loungers, umbrellas, and a refreshing poolside bar. Just steps from Ocean City Boardwalk's attractions and pristine beaches.
$83 nightly
The price is $93
Nov 17 - Nov 18
Total with taxes and fees
Hyatt Place Ocean City / Oceanfront

Grand Hotel Ocean City Oceanfront

3.0 star property
Downtown Ocean City
  • Outdoor pool
  • Indoor pool
  • Poolside bar
  • On the beach
9.0 out of 10, Wonderful, (3303)
Splash between seasons at dual swimming havens while enjoying poolside cocktails and ocean-view dining. After refreshing dips, explore the sauna, fitness center, or oceanfront terrace before returning to spacious rooms with private balconies.
$76 nightly
The price is $85
Nov 9 - Nov 10
Total with taxes and fees
Grand Hotel Ocean City Oceanfront

Fenwick Inn

3.0 star property
North Ocean City
  • Indoor pool
  • Near the beach
8.8 out of 10, Excellent, (1984)
Vibrant indoor aquatic center offers year-round swimming and a relaxing hot tub after beach adventures. Families appreciate the splash pad and arcade room, while the 8th-floor restaurant serves excellent meals with beautiful views.
$75 nightly
The price is $83
Nov 24 - Nov 25
Total with taxes and fees
Fenwick Inn

Hyatt Regency Chesapeake Bay

4.0 star property
Cambridge
  • 2 outdoor pools
  • Indoor pool
  • Poolside bar
  • Pool loungers
  • On private beach
  • Hot tub
8.8 out of 10, Excellent, (1014)
Splash down the waterslide into aquatic bliss at this riverside resort's multiple pools. Guests enjoy poolside dining, a hot tub retreat, and sun loungers for ultimate relaxation, all complemented by golf, tennis, and spa treatments nearby.
$184 nightly
The price is $209
Nov 23 - Nov 24
Total with taxes and fees
Hyatt Regency Chesapeake Bay

Comfort Inn & Suites Cambridge

2.5 star property
Cambridge
  • Indoor pool
8.2 out of 10, Very Good, (781)
Swimming enthusiasts delight in the temperature-controlled indoor pool, open from 9:00 AM to 10:00 PM daily. Beyond aquatic recreation, guests appreciate free bicycles for exploring nearby Choptank River Lighthouse and the consistently praised breakfast buffet.
$110 nightly
The price is $122
Nov 30 - Dec 1
Total with taxes and fees
Comfort Inn & Suites Cambridge

Aloft Ocean City

3.0 star property
Midtown Ocean City
  • Indoor pool
  • Poolside bar
  • Pool umbrellas
  • On the beach
9.0 out of 10, Wonderful, (1001)
Poolside bar service complements the sun-soaked outdoor swimming area and tranquil indoor pool. Guests appreciate the beachfront location, with yoga classes offered right on the sand, and free bicycle rentals for exploring vibrant Ocean City.
$76 nightly
The price is $84
Nov 16 - Nov 17
Total with taxes and fees
Aloft Ocean City

Hilton Ocean City Oceanfront Suites

4.0 star property
Midtown Ocean City
  • Indoor pool
  • Poolside bar
  • Pool loungers
  • On the beach
  • Hot tub
8.8 out of 10, Excellent, (1303)
Glide through the resort's signature lazy river or plunge down the waterslide before unwinding in the hot tub. Multiple pools cater to every mood, with swim-up and poolside bars serving refreshing drinks as ocean views create a perfect waterfront escape.
$111 nightly
The price is $123
Nov 16 - Nov 17
Total with taxes and fees
Hilton Ocean City Oceanfront Suites
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.

Top Eastern Shore Hotel Reviews

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