Find Hotels with Pool in Eastern Shore, MD

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Check prices for these dates

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for Eastern Shore hotels with a pool

A resort with a large pool, outdoor seating, and a view of the sea.

1. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Aquatic paradise awaits with 2 outdoor pools, indoor pool, and waterslide offering year-round relaxation at this riverside resort.
The price is £144
includes taxes & fees
23 Nov - 24 Nov
Hyatt Regency Chesapeake Bay
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

2. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is £84
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
A multi-story hotel with a pool area, balconies, and a view of the ocean.

3. Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
3.0 star property
Downtown Ocean City
9.0 out of 10, Wonderful, (4,005 reviews)
  • cleanliness
    Float in indoor or outdoor pools with oceanfront views in this beach retreat.
The price is £54
includes taxes & fees
10 Nov - 11 Nov
Grand Hotel Ocean City Oceanfront
A two-story building with a covered entrance and an American flag.

4. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.0 out of 10, Very good, (1,005 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is £62
includes taxes & fees
8 Dec - 9 Dec
St Michaels Inn
A pool area with lounge chairs, a hot tub, and a view of the ocean.

5. Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center
2.5 star property
Midtown Ocean City
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Dive into coastal tranquility at the bayfront hotel with year-round pool access and poolside bar service.
The price is £49
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.

6. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
4.0 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Plunge into ocean views at this beachfront hotel with 3 pools, where sun-drenched relaxation meets poolside cocktail service.
The price is £68
includes taxes & fees
15 Nov - 16 Nov
DoubleTree by Hilton Ocean City Oceanfront
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.

7. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (858 reviews)
  • cleanliness
    Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
The price is £111
includes taxes & fees
15 Nov - 16 Nov
Hyatt Place Kent Narrows & Marina
A balcony with a view of a body of water, a row of buildings, and a chair.

8. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
The price is £100
includes taxes & fees
18 Nov - 19 Nov
Hilton Garden Inn Kent Island Marina
A large indoor swimming pool with wooden beams, white walls, and lounge chairs along the sides.

9. Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
3.0 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1,484 reviews)
  • cleanliness
    Oceanfront indoor pool sanctuary with modern loungers and beach yoga classes creates a perfect aquatic escape any season.
The price is £58
includes taxes & fees
17 Nov - 18 Nov
Hilton Garden Inn Ocean City Oceanfront
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

10. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,003 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is £75
includes taxes & fees
15 Nov - 16 Nov
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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Choose what matters most at hotels with a pool in Eastern Shore

Breakfast included
4 stars

Top Eastern Shore Hotel Reviews

A covered outdoor patio with tables and chairs, umbrellas, and a pool in the background.
The Avenue Inn and Spa

The Avenue Inn and Spa

The Avenue Inn and Spa
Downtown

10/10 Excellent

Staff were very helpful and friendly, the place was very clean and extremely comfortable. Had great touches and was just a wonderful place to stay. Would highly recommend.
United Kingdom
John
Reviewed July 11, 2026
The Avenue Inn and Spa

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