Eastern Shore Hotel Guide - Hotels with Pool in Eastern Shore, Maryland

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Top Eastern Shore Hotels with Pool

DoubleTree by Hilton Ocean City Oceanfront
4.0 star property
  • 2 outdoor pools
  • Indoor pool
  • Poolside bar
  • Pool loungers
  • On the beach
9.0 out of 10, Wonderful, (1000)
Sparkling indoor and outdoor pools invite swimmers year-round, with sun loungers perfectly positioned for ocean gazing. After cooling off, guests savour handcrafted drinks at the poolside bar while planning beach adventures just steps away.
The price is €78
includes taxes & fees
2 Dec - 3 Dec
DoubleTree by Hilton Ocean City Oceanfront
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
  • 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.
The price is €92
includes taxes & fees
23 Nov - 24 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
Hyatt Place Ocean City / Oceanfront
3.0 star property
  • Indoor pool
  • Poolside bar
  • Pool loungers
  • On the beach
9.0 out of 10, Wonderful, (1583)
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.
The price is €80
includes taxes & fees
17 Nov - 18 Nov
Hyatt Place Ocean City / Oceanfront
Grand Hotel Ocean City Oceanfront
3.0 star property
  • Outdoor pool
  • Indoor pool
  • Poolside bar
  • On the beach
9.0 out of 10, Wonderful, (3319)
Splash between seasons at dual swimming havens while enjoying poolside cocktails and ocean-view dining. After refreshing dips, explore the sauna, fitness centre, or oceanfront terrace before returning to spacious rooms with private balconies.
Grand Hotel Ocean City Oceanfront
Hilton Garden Inn Ocean City Oceanfront
3.0 star property
  • Indoor pool
  • Pool loungers
  • On the beach
9.0 out of 10, Wonderful, (1080)
Sparkling waters beckon year-round at the indoor pool, complete with plush loungers and adjacent fitness centre featuring a Peloton bike. After swimming, guests savour ocean views at Solstice Bar & Grill before joining morning beach yoga classes.
The price is €65
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Ocean City Oceanfront
Hilton Ocean City Oceanfront Suites
4.0 star property
  • Indoor pool
  • Poolside bar
  • Pool loungers
  • On the beach
  • Hot tub
8.8 out of 10, Excellent, (1306)
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.
The price is €106
includes taxes & fees
11 Nov - 12 Nov
Hilton Ocean City Oceanfront Suites
Hyatt Regency Chesapeake Bay
4.0 star property
  • 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.
The price is €182
includes taxes & fees
23 Nov - 24 Nov
Hyatt Regency Chesapeake Bay
Comfort Inn & Suites Cambridge
2.5 star property
  • Indoor pool
8.2 out of 10, Very good, (779)
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.
The price is €106
includes taxes & fees
30 Nov - 1 Dec
Comfort Inn & Suites Cambridge
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
2.5 star property
  • Indoor pool
  • Poolside bar
  • Near the beach
8.8 out of 10, Excellent, (1015)
Poolside refreshment awaits at the swim-up bar, complementing both the year-round indoor sanctuary and sun-drenched seasonal outdoor pool. Guests praise the immaculate facilities just steps from Ocean City's sandy beaches and boardwalk attractions.
The price is €57
includes taxes & fees
26 Nov - 27 Nov
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Fenwick Inn
3.0 star property
  • Indoor pool
  • Near the beach
8.8 out of 10, Excellent, (2020)
Vibrant indoor aquatic centre 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.
Fenwick 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.

Top Eastern Shore Hotel Reviews

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