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

Find Hotels with a Pool in Eastern Shore, MD

Check availability on Eastern Shore Hotels with a Pool

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Oct 20 - Oct 21
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Oct 21 - Oct 22
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Oct 23 - Oct 25
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Our top choices for Eastern Shore hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
Two Adirondack chairs facing a calm body of water with a clear sky above.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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.
$105 nightly
$117 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
Exterior
Room
A gym with exercise equipment, a bench, and a wall-mounted mirror.

2. 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.
$90 nightly
$100 total
Nov 8 - Nov 9
Total with taxes and fees
Best Western Kent Narrows Inn
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A marina with boats docked, a sandy beach, and a clear blue sky.
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.

3. 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.
$171 nightly
$194 total
Nov 18 - Nov 19
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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.
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.

4. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.
$89 nightly
$98 total
Oct 21 - Oct 22
Total with taxes and fees
Baymont by Wyndham Easton
A large indoor swimming pool with wooden beams, white walls, and lounge chairs along the sides.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.
A balcony with wicker furniture overlooking a beach.
A beach chair under a blue umbrella on a sandy beach with the ocean in the background.

5. Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
  • Oceanfront indoor pool sanctuary with modern loungers and beach yoga classes creates a perfect aquatic escape any season.
$65 nightly
$73 total
Nov 8 - Nov 9
Total with taxes and fees
Hilton Garden Inn Ocean City Oceanfront
A swimming pool with a 5ft depth marker, white lounge chairs, and tables arranged around the pool area.
A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".
A hotel room with a desk, chair, blue sofa, ottoman, and a hallway leading to a door.
A spacious lobby with a reception desk, seating area, and a television screen.

6. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$110 nightly
$122 total
Oct 27 - Oct 28
Total with taxes and fees
Comfort Inn & Suites Cambridge
An indoor swimming pool with clear views of boats and water.
A patio with outdoor seating, overlooking a marina with boats.
A balcony with a view of a body of water, a row of buildings, and a chair.
A balcony with a view of a marina and row houses.

7. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
  • Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
$125 nightly
$138 total
Nov 18 - Nov 19
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A spacious lobby with a staircase, a reception desk, and a dining area.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A hotel room with a bed, a sofa, a desk, and two chairs. There are two lamps on the desk and a picture frame on the wall.

8. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
  • Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
$83 nightly
$93 total
Nov 15 - Nov 16
Total with taxes and fees
Quality Inn Grasonville near Kent Island
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
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.

9. 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.
$128 nightly
$141 total
Oct 29 - Oct 30
Total with taxes and fees
Hampton Inn Easton
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.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

10. 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.
$135 nightly
$149 total
Oct 25 - Oct 26
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
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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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A modern food court with a central island, various food stations, and a yogurt display.
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
$105 nightly
$117 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Room
Exterior
A lobby with a reception desk, a clock, and a wall-mounted deer head.
A gym with exercise equipment, a bench, and a wall-mounted mirror.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
$90 nightly
$100 total
Nov 8 - Nov 9
Total with taxes and fees
Best Western Kent Narrows Inn
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A marina with boats docked, a sandy beach, and a clear blue sky.
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.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$171 nightly
$194 total
Nov 18 - Nov 19
Total with taxes and fees
Hyatt Regency Chesapeake Bay
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
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.
A gym with a treadmill, elliptical, and stationary bike.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
$89 nightly
$98 total
Oct 21 - Oct 22
Total with taxes and fees
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 beach chair under a blue umbrella on a sandy beach with the ocean in the background.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
$65 nightly
$73 total
Nov 8 - Nov 9
Total with taxes and fees
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 hotel room with a blue sofa, a desk with a chair, a lamp, and a picture on the wall.
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
$110 nightly
$122 total
Oct 27 - Oct 28
Total with taxes and fees
Comfort Inn & Suites Cambridge
A white door with a view of the sea through a window.
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.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
$125 nightly
$138 total
Nov 18 - Nov 19
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.
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
$83 nightly
$93 total
Nov 15 - Nov 16
Total with taxes and fees
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 swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

Hampton Inn Easton

Hampton Inn Easton
Easton
$128 nightly
$141 total
Oct 29 - Oct 30
Total with taxes and fees
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 with a covered entrance, multiple floors, and a parking lot.
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.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135 nightly
$149 total
Oct 25 - Oct 26
Total with taxes and fees
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 marina with boats docked, a sandy beach, and a clear blue sky.
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.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$171 nightly
$194 total
Nov 18 - Nov 19
Total with taxes and fees
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 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.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
$81 nightly
$91 total
Nov 8 - Nov 9
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
A dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.
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 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
$115 nightly
$129 total
Nov 1 - Nov 2
Total with taxes and fees
Hilton Ocean City Oceanfront Suites
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
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
$237 nightly
$263 total
Nov 15 - Nov 16
Total with taxes and fees
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 wooden console table with framed floral artwork, two lamps, and two ottomans.
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
$489 nightly
$538 total
Oct 21 - Oct 22
Total with taxes and fees
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

Fenwick Inn

Fenwick Inn

10/10 Excellent
"It was great! Clean room. Staff was great!"
Jeanne 2-night trip
Posted 10 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 12 hours ago
St Michaels Inn
Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"Hotel is old with small rooms. People are very nice and accommodating. Rooms are clean, however, not much countertop for makeup, hair products, jewelry and other necessities. We had a king size bed that was nice and comfortable but there was not room for a chair or any other option to sit other than on the bed. Nicely located on the boardwalk with places to eat in season. They supply coffee, but not in room, you have to go to the lobby to get it. Does have a nice size refrigerator and a microwave. Does not have a balcony. Nice front porch with rocking chairs. I could hear the person in the next room snoring, so the walls are a bit thin."
Janice 4-night trip
Posted 13 hours ago
Plim Plaza Hotel
Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG

10/10 Excellent
"The Holiday in is a great place to stay. Staff were Great! Would Definitely stay Again."
Valerie 2-night trip
Posted 22 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 1 day ago
Grand Hotel Ocean City Oceanfront

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