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 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
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.
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.
$110 nightly
$122 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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 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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

2. 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 29 - Sep 30
Total with taxes and fees
Best Western Plus Easton Inn & Suites
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 covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

3. 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 29 - Sep 30
Total with taxes and fees
Baymont by Wyndham Easton
A swimming pool with a 5ft depth marker, white lounge chairs, and tables arranged around the pool area.
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 wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

4. 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
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 beachfront hotel with multiple balconies overlooking the ocean.
A lobby with green sofas, a round table with a plant, and a lantern.

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.
$74 nightly
$82 total
Oct 28 - Oct 29
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
A multi-level hotel with a central pool area, multiple balconies, and indoor seating areas.
A beachfront hotel with multiple floors, balconies, and a large glass facade.
A restaurant with a high ceiling, large windows, and a view of the sunset.
A balcony with a view of the ocean, featuring a railing and blue chairs.

6. Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort
North Ocean City
  • Luxurious indoor pool retreat with beachfront bliss makes this ocean getaway a splash.
$108 nightly
$119 total
Oct 18 - Oct 19
Total with taxes and fees
Princess Royale Oceanfront Resort
An indoor swimming pool with clear water, tiled steps, and orange lounge chairs.
A modern house with a glass door entrance, outdoor seating area with chairs, and a small table.
A hotel room with two beds, a large window with a city view, a flat-screen TV, and a desk with a lamp.
A hotel reception area with a herringbone patterned floor, reception desks, a flat-screen TV, and a view of the lobby.

7. Fenwick Inn

Fenwick Inn
North Ocean City
  • Dive into resort-style relaxation at this indoor pool oasis just steps from Maryland Beach.
$84 nightly
$95 total
Oct 12 - Oct 13
Total with taxes and fees
Fenwick Inn
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.

8. 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
A multi-story hotel with a pool area, including sun loungers and a smaller pool.
A multi-story hotel with balconies, a beachside location, and various shops and restaurants.
A beach with umbrellas and people.
A terrace with white plastic chairs and tables, blue umbrellas, and potted plants.

9. Park Place Hotel

Park Place Hotel
Downtown Ocean City
  • Relax at the oceanfront seasonal pool with loungers and umbrellas, just steps from the boardwalk for a perfect beach getaway.
$83 nightly
$92 total
Oct 13 - Oct 14
Total with taxes and fees
Park Place Hotel
A swimming pool with red and white striped lounge chairs and umbrellas, surrounded by a fence and trees.
A beachside restaurant with outdoor seating and umbrellas.
A hotel room with a bed, a green sofa, a small table, a chair, a window with curtains, and a painting on the wall.
A castle-like building with a swimming pool, surrounded by trees and illuminated by street lights.

10. Castle in the Sand

Castle in the Sand
Midtown Ocean City
  • Shimmering oceanfront pool paradise delivers refreshing dips with beach views just steps away.
$71 nightly
$80 total
Sep 29 - Sep 30
Total with taxes and fees
Castle in the Sand
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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 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 pool area with multiple pools, lounge chairs, and a pool lift.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$129 nightly
$142 total
Sep 29 - Sep 30
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 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
$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 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.
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
$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 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 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 29 - Sep 30
Total with taxes and fees
Baymont by Wyndham Easton
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 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.

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 spacious lobby with a mix of seating options, including sofas and chairs, and a bar area with stools.
A Hampton Inn & Suites with a covered entrance, brick facade, and well-maintained landscaping.

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 restaurant with a bar area, seating, and a kitchen in the background.
A hotel with a prominent 'Best Western' sign, a brick facade, and a covered entrance.

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 with a covered entrance, multiple windows, and a brick facade.
An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables.
A hotel room with a large bathtub, a red chair, a small round table, and a bed with white linens.

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.
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.
A hotel room with a large bed, bedside lamps, a nightstand, a window with blinds, and a wall-mounted abstract painting.

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.
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.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
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
$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 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.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$250 nightly
$284 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 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.
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
$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 swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
A beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.
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
$98 nightly
$109 total
Oct 19 - Oct 20
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 wooden console table with framed floral artwork, two lamps, and two ottomans.
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
$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

Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"We had an absolute blast staying here. The staff and the other guests were great! We were there for the Nor’Easter and although the Oceans Calling Festival was cancelled and the weather was awful we still had fun. We did cut our stay short due to deteriorating weather conditions, but booked for next year before we left. If you want a clean place to stay and want to be surrounded by all the OC Boardwalk has to offer, look no further. Yes, the rooms are small but what are you doing in your room? Go outside, hang out on the porch or the huge lobby. So much fun."
Lori 4-night trip
Posted 1 hour ago
Plim Plaza Hotel
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"5"
David 4-night trip
Posted 1 hour ago
Days Inn by Wyndham Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

8/10 Good
"Nice indoor pool, and the small kitchen and living area was roomy. It was a very comfortable place to stay."
Bethany 2-night trip
Posted 1 hour ago
Princess Royale Oceanfront Resort
Bonita Beach Hotel

Bonita Beach Hotel

10/10 Excellent
"Able to get early check-in which was nice. Room was clean and offered all the amenities needed to enjoy our stay. Room was very useful for a longer stay than just one or two nights"
Jeremy 1-night trip
Posted 2 hours ago
Bonita Beach Hotel
Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

8/10 Good
"No body soap in the bathroom."
Michael 4-night trip
Posted 3 hours ago
Holiday Inn & Suites Ocean City by IHG
Crystal Beach Hotel

Crystal Beach Hotel

8/10 Good
"Great value, can’t beat the location. We stayed in a dog friendly room, I would suggest removing carpet from these toiles to help with odor. Really happy overall for the value and plan to come back to this hotel."
Louis 2-night trip
Posted 4 hours ago
Crystal Beach Hotel
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 8 hours ago
Comfort Suites Ocean City West
Quality Inn Oceanfront

Quality Inn Oceanfront

8/10 Good
"bathroom tub and fixtures needs to be upgraded. Staff is both courtesy and helpful."
Robin 2-night trip
Posted 20 hours ago
Quality Inn Oceanfront

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