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

Hotels with Swimming Pool in Eastern Shore, Maryland

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Check availability on Eastern Shore Hotels with Swimming Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
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 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.

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.
P6,623
P7,352 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 hotel with a covered entrance, multiple floors, and a parking lot.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

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.
P8,525
P9,377 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield Inn & Suites by Marriott Easton
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
An outdoor event area with round tables and a view of the water.
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.
P9,588
P10,642 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Place Kent Narrows & Marina
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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
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.

4. 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.
P7,506
P8,257 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Plus Easton Inn & Suites
A deck with white lounge chairs and a pool, overlooking a beach.
A hotel room with two beds, a desk, and a chair. There is a window with curtains, a lamp, and a nightstand with a phone.
A beach view from a balcony with a clear sky.
A balcony with two green Adirondack chairs facing a beach.

5. 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.
P4,236
P4,744 total
includes taxes & fees
Nov 19 - Nov 20
Comfort Inn Ocean City Boardwalk
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a sandy beach, and a clear blue sky.

6. 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.
P10,155
P13,328 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A poolside area with blue lounge chairs and yellow umbrellas, a sign for Grand Hotel, and palm trees in the background.
A hotel room with two beds, a balcony, a dining area, and a view of the city.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.
A beachfront hotel with multiple balconies overlooking the ocean.

7. 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.
P4,062
P4,550 total
includes taxes & fees
Nov 1 - Nov 2
Grand Hotel Ocean City Oceanfront
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
Room
A wooden pavilion with picnic tables and benches, a grill, and a red bench.
A snack and beverage section with shelves stocked with various snacks and a refrigerator with bottled drinks.

8. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
  • Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
P5,669
P6,293 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Kent Narrows Inn
A swimming pool with lounge chairs and a pergola under a clear sky.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
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.

9. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
  • Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.
P13,487
P16,576 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Chesapeake Bay Beach Club
Pool
A hotel room with a gray sofa, a small ottoman, a bed with white bedding, a nightstand with a lamp, a wall-mounted TV, and a mirror with a pink frame.
Private kitchen
Exterior

10. Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland
Fruitland
P6,648
P7,446 total
includes taxes & fees
Nov 9 - Nov 10
Home2 Suites By Hilton Salisbury Fruitland
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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 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.
A modern food court with a central island, various food stations, and a yogurt display.
A reception desk with a modern design, a digital display, and a check-in counter.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
P6,623
P7,352 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
Room
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.
A restaurant with a counter, seating area, and a clock on the wall.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
P5,669
P6,293 total
includes taxes & fees
Nov 8 - Nov 9
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 a view of the water, featuring a modern design with a marble floor and contemporary furniture.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a sandy beach, and a clear blue sky.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
P10,155
P13,328 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 swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
P5,612
P6,173 total
includes taxes & fees
Nov 2 - Nov 3
Baymont by Wyndham Easton
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A spacious dining area with multiple tables and chairs, large windows offering a view of the ocean, and a modern interior design.
A water park with multiple slides and pools, including a large green water slide and a lazy river.
A beach chair under a blue umbrella on a sandy beach with the ocean in the background.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
P4,086
P4,576 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Ocean City Oceanfront
A spacious lobby with a reception desk, seating area, and a television screen.
A hotel room with a desk, chair, blue sofa, ottoman, and a hallway leading to a door.
A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".
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
P6,936
P7,699 total
includes taxes & fees
Oct 28 - Oct 29
Comfort Inn & Suites Cambridge
A patio with outdoor seating, overlooking a marina with boats.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
An indoor swimming pool with clear views of boats and water.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
P7,862
P8,727 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 hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A spacious lobby with a staircase, a reception desk, and a dining area.

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
P5,263
P5,842 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 hotel hallway with carpeted floors, white doors, and overhead lighting.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

Hampton Inn Easton

Hampton Inn Easton
Easton
P8,054
P8,859 total
includes taxes & fees
Nov 1 - Nov 2
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.
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
A hotel with a covered entrance, multiple floors, and a parking lot.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
P8,525
P9,377 total
includes taxes & fees
Oct 25 - Oct 26
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 a view of the water, featuring a modern design with a marble floor and contemporary furniture.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a sandy beach, and a clear blue sky.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
P10,155
P13,328 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 living room with a beige sofa, blue and red patterned pillows, a wooden coffee table, and a view of the ocean through large windows.
A beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.
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.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
P5,115
P5,729 total
includes taxes & fees
Nov 3 - Nov 4
DoubleTree by Hilton Ocean City Oceanfront
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
A balcony with a round table and chairs, overlooking the beach and ocean.
A dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
P7,238
P8,107 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 bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
P13,487
P16,576 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 white colonial-style house with a covered porch, brick steps, and outdoor seating.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.

The Oaks Waterfront

The Oaks Waterfront
Easton
P27,718
P30,489 total
includes taxes & fees
Nov 2 - Nov 3
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 3 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 4 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 10 hours ago
Holiday Inn Ocean City by IHG
Fenwick Inn

Fenwick Inn

10/10 Excellent
"It was great! Clean room. Staff was great!"
Jeanne 2-night trip
Posted 21 hours ago
Fenwick Inn
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Staff was exceptional. Historical vibe was fun and coastal-appropriate. Close to DC and other fun destinations."
Kelly 4-night trip
Posted 23 hours ago
St Michaels Inn
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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