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
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Eastern Shore hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
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.
Two Adirondack chairs facing a calm body of water with a clear sky above.

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.
$110 nightly
$122 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.
A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

2. 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.
$99 nightly
$109 total
Sep 30 - Oct 1
Total with taxes and fees
Baymont by Wyndham Easton
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
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.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

3. 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.
$129 nightly
$142 total
Sep 30 - Oct 1
Total with taxes and fees
Best Western Plus Easton Inn & Suites
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.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
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.

4. 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 4 - Oct 5
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A swimming pool with a 5ft depth marker, white lounge chairs, and tables arranged around the pool area.
A spacious lobby with a reception desk, seating area, and a television screen.
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.

5. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$116 nightly
$129 total
Oct 27 - Oct 28
Total with taxes and fees
Comfort Inn & Suites Cambridge
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A bathroom with a toilet, a bathtub, and a shower area.
Exterior
A lobby with a reception desk, a clock, and a wall-mounted deer head.

6. 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.
$108 nightly
$120 total
Oct 6 - Oct 7
Total with taxes and fees
Best Western Kent Narrows Inn
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 lobby with green sofas, a round table with a plant, and a lantern.

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.
$74 nightly
$82 total
Oct 28 - Oct 29
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
A resort with a swimming pool, sun loungers, and a view of the ocean.
A beachside resort with sun loungers, umbrellas, and a view of the ocean.
A hotel room with a large bed, a desk with a chair, a TV, and a balcony with a view of the sea.
A fire pit in the center of a courtyard with lounge chairs and umbrellas in the background.

8. Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG
North Ocean City
  • Luxurious swim-up bar beckons at this oceanfront hotel, where two pools and hot tubs create the ultimate aquatic retreat.
$75 nightly
$84 total
Oct 29 - Oct 30
Total with taxes and fees
Holiday Inn Ocean City by IHG
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 marina and row houses.
A balcony with a view of a body of water, a row of buildings, and a chair.

9. 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.
$147 nightly
$163 total
Oct 6 - Oct 7
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
An outdoor event area with round tables and a view of the water.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

10. 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.
$152 nightly
$169 total
Oct 6 - Oct 7
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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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

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
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.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$129 nightly
$142 total
Sep 30 - Oct 1
Total with taxes and fees
Best Western Plus Easton Inn & Suites
Two Adirondack chairs facing a calm body of water with a clear sky above.
A reception desk with a modern design, a digital display, and a check-in counter.
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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
$110 nightly
$122 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
$152 nightly
$169 total
Oct 6 - Oct 7
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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.
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.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135 nightly
$149 total
Oct 4 - Oct 5
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
$99 nightly
$109 total
Sep 30 - Oct 1
Total with taxes and fees
Baymont by Wyndham Easton
A spacious lobby with a reception desk, seating area, and a television screen.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.
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.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
$116 nightly
$129 total
Oct 27 - Oct 28
Total with taxes and fees
Comfort Inn & Suites Cambridge
A modern indoor pool area with wooden beams, a pool, and seating arrangements.
A modern hotel room with a kitchenette, a large mirror, a flat-screen TV, and a sofa.
A Hampton Inn & Suites with a covered entrance, brick facade, and well-maintained landscaping.
A spacious lobby with a mix of seating options, including sofas and chairs, and a bar area with stools.

Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland
Fruitland
$122 nightly
$137 total
Oct 8 - Oct 9
Total with taxes and fees
Hampton Inn & Suites Salisbury/Fruitland
A swimming pool with a metal ladder, lounge chairs, and a small building in the background.
A hotel lobby with a reception desk, seating area, and a large wall mural.
A hotel with a prominent 'Best Western' sign, a brick facade, and a covered entrance.
A hotel room with a bed, a sofa, a desk, and a chair. There are two lamps on the nightstands, a television, and a window with curtains.

Best Western Denton Inn

Best Western Denton Inn
Denton
$119 nightly
$132 total
Oct 4 - Oct 5
Total with taxes and fees
Best Western Denton Inn
A spacious lobby with a wooden reception desk, a sofa, a staircase, and a reception area.
A hotel room with a large bathtub, a red chair, a small round table, and a bed with white linens.
A modern hotel room with a wooden floor, a red armchair, a grey sofa, a desk with a chair, and a lamp.
A hotel with a covered entrance, multiple windows, and a brick facade.

Country Inn & Suites by Radisson, Salisbury, MD

Country Inn & Suites by Radisson, Salisbury, MD
Salisbury
$90 nightly
$101 total
Oct 25 - Oct 26
Total with taxes and fees
Country Inn & Suites by Radisson, Salisbury, MD
A modern lobby with a reception desk, seating area, and artwork on the walls.
Exterior
A hotel room with a bed, a sofa, a TV, a desk, and a large window.
A modern restaurant with booths and tables, a kitchen area, and a large window.

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City
Pocomoke City
$127 nightly
$142 total
Oct 11 - Oct 12
Total with taxes and fees
Best Western Plus Pocomoke City
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4-star hotels with pools in Eastern Shore

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 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
$135 nightly
$152 total
Oct 25 - Oct 26
Total with taxes and fees
Hilton Ocean City Oceanfront Suites
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A spacious dining area with high ceilings, large windows, and modern chandeliers.
A marina with boats docked, a sandy beach, and a clear blue sky.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$254 nightly
$288 total
Oct 26 - Oct 27
Total with taxes and fees
Hyatt Regency Chesapeake Bay
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
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.

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
$214 nightly
$238 total
Oct 19 - Oct 20
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
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.
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
$97 nightly
$109 total
Oct 13 - Oct 14
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
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 deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.

The Oaks Waterfront

The Oaks Waterfront
Easton
$489 nightly
$538 total
Sep 30 - Oct 1
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

Castle in the Sand

Castle in the Sand

10/10 Excellent
"Nice front desk guy. Typical OC room but clean"
Mike 2-night trip
Posted 12 hours ago
Castle in the Sand
Bonita Beach Hotel

Bonita Beach Hotel

8/10 Good
"I had a few mechanical issues like one electrical outlet not working, no working room telephone and the shower handle coming off in your hand."
Denise 4-night trip
Posted 17 hours ago
Bonita Beach Hotel
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"Loved that it was clean and the labels on the shower shampoos and soaps were large enough for my 57year old eyes to read."
Jenn 3-night trip
Posted 20 hours ago
Days Inn by Wyndham Ocean City Oceanfront
Comfort Suites Ocean City West

Comfort Suites Ocean City West

8/10 Good
"The front desk staff was extremely helpful and courteous. The hotel, including the rooms were very clean. My only complaint being that when I returned from swimming in the pool one afternoon, that my room door was propped open by the housekeeping staff, with none of them in sight. I stood by for several minutes to see if anyone would return or was keeping an eye on the room, but nobody did. This was a little disconcerting as I had left valuable camera equipment along with my wallet, in the room while swimming. Nothing was missing but these actions left the room unsecure and anyone in the hotel could have easily gained access to it!"
Michael 3-night trip
Posted 1 day ago
Comfort Suites Ocean City West

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