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

Find Hotels with a Pool in Eastern Shore, MD

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Check availability on Eastern Shore Hotels with a Pool

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Eastern Shore hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
Two Adirondack chairs facing a calm body of water with a clear sky above.
A modern food court with a central island, various food stations, and a yogurt display.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
￥16,619
￥18,448 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

2. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
  • Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.
￥21,392
￥23,531 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Easton
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
  • Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
￥23,584
￥26,178 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Place Kent Narrows & Marina
A deck with white lounge chairs and a pool, overlooking a beach.
A beach view from a balcony with a clear sky.
A beach view with a white fence, two green Adirondack chairs, and a white lounge chair.
A balcony with two green Adirondack chairs facing a beach.

4. Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk
Downtown Ocean City
  • Splash into poolside paradise at the heart of Ocean City with indoor and seasonal outdoor pools.
￥10,629
￥11,903 total
includes taxes & fees
Nov 19 - Nov 20
Comfort Inn Ocean City Boardwalk
A poolside area with blue lounge chairs and yellow umbrellas, a sign for Grand Hotel, and palm trees in the background.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.
A hotel room with two beds, a balcony, a dining area, and a view of the city.
A beachfront hotel with multiple balconies overlooking the ocean.

5. Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
  • Float in indoor or outdoor pools with oceanfront views in this beach retreat.
￥10,193
￥11,417 total
includes taxes & fees
Nov 1 - Nov 2
Grand Hotel Ocean City Oceanfront
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.
A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

6. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
  • Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
￥18,835
￥20,719 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Plus Easton Inn & Suites
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
A hotel hallway with carpeted floors, white doors, and overhead lighting.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.
A modern hotel dining area with a long table, four chairs, and three pendant lights.

7. Hampton Inn Easton

Hampton Inn Easton
Easton
  • Dive into refreshing luxury at this Easton hotel with a pristine indoor pool and fitness center for your aquatic escape.
￥20,241
￥22,265 total
includes taxes & fees
Oct 29 - Oct 30
Hampton Inn Easton
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with high ceilings, large windows, and modern chandeliers.
A spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.

8. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Aquatic paradise awaits with 2 outdoor pools, indoor pool, and waterslide offering year-round relaxation at this riverside resort.
￥23,109
￥30,748 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
A bar area with a long counter, multiple bar stools, and a pool table. There are tables and chairs for dining, and the room has large windows.
A living room with a beige sofa, blue and red patterned pillows, a wooden coffee table, and a view of the ocean through large windows.

9. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
  • Plunge into ocean views at this beachfront hotel with 3 pools, where sun-drenched relaxation meets poolside cocktail service.
￥12,849
￥14,391 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Ocean City Oceanfront
A person sitting by a poolside with orange chairs and a drink.
A dining area with a table set for two, potted plants, and a view through large windows.
A balcony with two chairs and a table, overlooking a body of water and distant land.
A balcony with white railings and orange chairs, overlooking a body of water and a distant shoreline.

10. Cambria Hotel Ocean City - Bayfront

Cambria Hotel Ocean City - Bayfront
Downtown Ocean City
  • Poolside paradise beckons with year-round swimming options in this bayside retreat.
￥13,169
￥17,123 total
includes taxes & fees
Nov 12 - Nov 13
Cambria Hotel Ocean City - Bayfront
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Choose what matters most at hotels with a pool in Eastern Shore

Breakfast included
4 stars
5 stars
Hot tub
Spa

Hotels with pools and free breakfast in Eastern Shore

Two Adirondack chairs facing a calm body of water with a clear sky above.
A modern food court with a central island, various food stations, and a yogurt display.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
￥16,619
￥18,448 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
Room
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A poolside area with lounge chairs and a mural of a sunset over water.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
￥14,226
￥15,792 total
includes taxes & fees
Nov 11 - Nov 12
Best Western Kent Narrows Inn
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with high ceilings, large windows, and modern chandeliers.
A spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
￥23,109
￥30,748 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A gym with a treadmill, elliptical, and stationary bike.
A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
￥14,103
￥15,513 total
includes taxes & fees
Nov 1 - Nov 2
Baymont by Wyndham Easton
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.
A water park with multiple slides and pools, including a large green water slide and a lazy river.
A spacious dining area with multiple tables and chairs, large windows offering a view of the ocean, and a modern interior design.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
￥10,253
￥11,483 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Ocean City Oceanfront
A spacious lobby with a reception desk, seating area, and a television screen.
A hotel room with a blue sofa, a desk with a chair, a lamp, and a picture on the wall.
A hotel room with a desk, chair, blue sofa, ottoman, and a hallway leading to a door.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
￥17,436
￥19,354 total
includes taxes & fees
Oct 27 - Oct 28
Comfort Inn & Suites Cambridge
A patio with outdoor seating, overlooking a marina with boats.
An indoor swimming pool with clear views of boats and water.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
￥19,728
￥21,898 total
includes taxes & fees
Nov 18 - Nov 19
Hilton Garden Inn Kent Island Marina
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A spacious lobby with a staircase, a reception desk, and a dining area.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
￥13,207
￥14,661 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Grasonville near Kent Island
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.
A hotel hallway with carpeted floors, white doors, and overhead lighting.

Hampton Inn Easton

Hampton Inn Easton
Easton
￥20,241
￥22,265 total
includes taxes & fees
Oct 29 - Oct 30
Hampton Inn Easton
A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
A hotel with a covered entrance, multiple floors, and a parking lot.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
￥21,392
￥23,531 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Easton
View all properties

4-star hotels with pools in Eastern Shore

An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with high ceilings, large windows, and modern chandeliers.
A spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
￥23,109
￥30,748 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
A bar area with a long counter, multiple bar stools, and a pool table. There are tables and chairs for dining, and the room has large windows.
A living room with a beige sofa, blue and red patterned pillows, a wooden coffee table, and a view of the ocean through large windows.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
￥12,849
￥14,391 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Ocean City Oceanfront
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
A large, multi-story hotel with a prominent Hilton sign, a parking lot with several cars, and a view of the ocean in the background.
A dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.
A balcony with a round table and chairs, overlooking the beach and ocean.

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
￥18,163
￥20,341 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Ocean City Oceanfront Suites
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
￥33,845
￥41,595 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Chesapeake Bay Beach Club
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

The Oaks Waterfront

The Oaks Waterfront
Easton
￥69,659
￥76,625 total
includes taxes & fees
Nov 1 - Nov 2
The Oaks Waterfront
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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Top Eastern Shore Hotel Reviews

Castle in the Sand

Castle in the Sand

10/10 Excellent
"Great front office staff. Made me feel welcome from the get-go. Nice overall set-up with a restaurant on the premises and an outdoor bar with live music."
Robert 3-night trip
Posted 11 hours ago
Castle in the Sand
The Americana Hotel

The Americana Hotel

8/10 Good
"The only problem I had with this stay was Ac was not that cold but other than that everything was fine."
Deandre 3-night trip
Posted 12 hours ago
The Americana Hotel
Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG

10/10 Excellent
"Room was clean, bed was comfortable. Hot tubs and pools were great! When indoor hot tubs wouldn't turn on, we approached the front desk. They called maintenance before we even turned away, and he arrived to fix them as we were walking back in! Took mere seconds, and he had the jets back up and running!"
Francine 2-night trip
Posted 18 hours ago
Holiday Inn Ocean City by IHG
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"We found our room to be surprisingly spacious, very clean, and comfortable; however, the kitchenette/bathroom areas were a bit dated. The property location was excellent and there were restaurants and a pool within the property. The common areas inside the hotel and the outdoor space at the front of the hotel were adequate, but guests were somewhat disrespectful, leaving their trash, not replacing chairs after their use, etc... The staff was pleasant enough when checking-in and helpful when we had a question but were ignoring simple tasks like straightening up the common areas when time allowed. Although this was a little off-putting, we would return if the opportunity presented itself."
Keli 1-night trip
Posted 2 days ago
Grand Hotel Ocean City Oceanfront
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"Great area to stay in plenty of great places to eat in walking distance and an excellent room with amazing room service"
Liam 3-night trip
Posted 2 days ago
Crystal Beach Hotel

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