A marina with numerous boats docked at wooden piers under a clear sky.

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

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Check availability on Eastern Shore Hotels with Pool

Our top choices for Eastern Shore hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

1. 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 €96
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
A swimming pool with blue water, surrounded by lounge chairs and umbrellas.

2. Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
3.0 star property
Downtown Ocean City
9.0 out of 10, Wonderful, (4,008 reviews)
  • cleanliness
    Float in indoor or outdoor pools with oceanfront views in this beach retreat.
The price is €54
includes taxes & fees
19 Nov - 20 Nov
Grand Hotel Ocean City Oceanfront
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

3. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is €90
includes taxes & fees
22 Nov - 23 Nov
Best Western Kent Narrows Inn
A resort with a large pool, outdoor seating, and a view of the sea.

4. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Aquatic paradise awaits with 2 outdoor pools, indoor pool, and waterslide offering year-round relaxation at this riverside resort.
The price is €200
includes taxes & fees
22 Nov - 23 Nov
Hyatt Regency Chesapeake Bay
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.

5. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (861 reviews)
  • cleanliness
    Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
The price is €135
includes taxes & fees
18 Nov - 19 Nov
Hyatt Place Kent Narrows & Marina
An indoor swimming pool with clear views of boats and water.

6. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
The price is €123
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Kent Island Marina
An indoor swimming pool with clear glass walls, a tiled floor, and a view of the sky.

7. Cambria Hotel Ocean City - Bayfront

Cambria Hotel Ocean City - Bayfront
3.0 star property
Downtown Ocean City
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Poolside paradise beckons with year-round swimming options in this bayside retreat.
The price is €82
includes taxes & fees
15 Dec - 16 Dec
Cambria Hotel Ocean City - Bayfront
A pool area with lounge chairs, a hot tub, and a view of the ocean.

8. 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, (1,000 reviews)
  • cleanliness
    Dive into coastal tranquility at the bayfront hotel with year-round pool access and poolside bar service.
The price is €59
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
A rooftop pool with lounge chairs and a building with balconies.

9. 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, (1,003 reviews)
  • cleanliness
    Plunge into ocean views at this beachfront hotel with 3 pools, where sun-drenched relaxation meets poolside cocktail service.
The price is €82
includes taxes & fees
22 Nov - 23 Nov
DoubleTree by Hilton Ocean City Oceanfront
A spacious lobby with a staircase, a reception desk, and a dining area.

10. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (1,004 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is €83
includes taxes & fees
13 Dec - 14 Dec
Quality Inn Grasonville near Kent Island
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

Hotels with pools and free breakfast in Eastern Shore

Two Adirondack chairs facing a calm body of water with a clear sky above.
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (1002)
The price is €96
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
View all properties

4-star hotels with pools in Eastern Shore

A resort with a large pool, outdoor seating, and a view of the sea.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1001)
The price is €200
includes taxes & fees
22 Nov - 23 Nov
Hyatt Regency Chesapeake Bay
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.
View all properties

Top Eastern Shore Hotel Reviews

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"We had a great stay! Everything was clean, staff helpful, great location! So peaceful off season, the outdoor heated pool was open through Nov. 15th and although the weather was fantastic, we didn’t get a swim in. Was disappointed that the tub/shower combo was the in-room hot tub. It would have been nicer to have the tub freestanding, I wasn’t comfortable using it. Overall, the value, the direct oceanfront location, amenities were perfect."
Pina 5-night trip
Posted 3 hours ago
Holiday Inn & Suites Ocean City by IHG

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