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

Find Hotels with a Pool in Eastern Shore, MD

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Eastern Shore Hotels with a Pool

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our top choices for Eastern Shore hotels with a pool

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 swimming pool with lounge chairs and umbrellas, surrounded by a white fence.
A modern bathroom with a large mirror, white sink, and toilet. There are towels hanging on hooks and a black bag on a hook.

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.
$123 nightly
$137 total
Sep 28 - Sep 29
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 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.

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 28 - Sep 29
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A hotel room with two beds, a chair, and a painting on the wall.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

3. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$87 nightly
$96 total
Sep 8 - Sep 9
Total with taxes and fees
St Michaels Inn
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 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.

4. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$114 nightly
$126 total
Sep 7 - Sep 8
Total with taxes and fees
Comfort Inn & Suites Cambridge
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 lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
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.

5. 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
Sep 3 - Sep 4
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.
A hotel room with a large bed, a desk, a chair, and a view of the city through large windows.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.

6. Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
  • Oceanside pool escape in Maryland features refreshing indoor and seasonal outdoor pool with poolside loungers and bar service.
$118 nightly
$132 total
Sep 17 - Sep 18
Total with taxes and fees
Hyatt Place 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 hotel room with a bed, two blue chairs, a table, and a view of the beach.
A balcony with a view of the ocean, featuring a railing and blue chairs.

7. Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort
North Ocean City
  • Luxurious indoor pool retreat with beachfront bliss makes this ocean getaway a splash.
$131 nightly
$145 total
Sep 30 - Oct 1
Total with taxes and fees
Princess Royale Oceanfront Resort
An indoor swimming pool with clear water, tiled steps, and orange lounge chairs.
A modern lounge area with multiple seating arrangements, including sofas and chairs, a central wooden planter, and ambient lighting.
A hotel room with two beds, a large window with a city view, a flat-screen TV, and a desk with a lamp.
A modern house with a glass door entrance, outdoor seating area with chairs, and a small table.

8. 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
Sep 21 - Sep 22
Total with taxes and fees
Fenwick Inn
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.

9. 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.
$117 nightly
$131 total
Sep 7 - Sep 8
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
A resort with a pool, beach, and outdoor seating area.
A spacious dining area with wooden tables and chairs, large windows offering views of the outdoors, and a ceiling with recessed lighting.
A hotel room with a bed, a sofa, a small table, two chairs, and a balcony with a view of the beach.
A balcony with a view of the ocean, featuring a railing and several Adirondack chairs.

10. Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums
North Ocean City
  • Splash into seaside bliss with year-round pools and beachfront relaxation at this coastal retreat.
$88 nightly
$98 total
Sep 30 - Oct 1
Total with taxes and fees
Carousel Resort Hotel & Condominiums
View all properties

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 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 swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
$123 nightly
$137 total
Sep 28 - Sep 29
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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 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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$129 nightly
$142 total
Sep 28 - Sep 29
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A two-story building with a covered entrance and an American flag.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A hotel room with two beds, a chair, and a painting on the wall.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

St Michaels Inn

St Michaels Inn
St. Michaels
$87 nightly
$96 total
Sep 8 - Sep 9
Total with taxes and fees
St Michaels Inn
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 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.
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
Sep 1 - Sep 2
Total with taxes and fees
Best Western Denton Inn
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 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
$114 nightly
$126 total
Sep 7 - Sep 8
Total with taxes and fees
Comfort Inn & Suites Cambridge
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 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.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135 nightly
$149 total
Sep 3 - Sep 4
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.
A hotel room with a large bed, a desk, a chair, and a view of the city through large windows.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
$118 nightly
$132 total
Sep 17 - Sep 18
Total with taxes and fees
Hyatt Place Ocean City / Oceanfront
An indoor swimming pool with clear water, tiled steps, and orange lounge chairs.
A modern lounge area with multiple seating arrangements, including sofas and chairs, a central wooden planter, and ambient lighting.
A hotel room with two beds, a large window with a city view, a flat-screen TV, and a desk with a lamp.
A modern house with a glass door entrance, outdoor seating area with chairs, and a small table.

Fenwick Inn

Fenwick Inn
North Ocean City
$84 nightly
$95 total
Sep 21 - Sep 22
Total with taxes and fees
Fenwick Inn
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 hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
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
$100 nightly
$111 total
Sep 28 - Sep 29
Total with taxes and fees
Quality Inn Grasonville near Kent Island
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 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 multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$254 nightly
$288 total
Sep 29 - Sep 30
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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 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 multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$254 nightly
$288 total
Sep 29 - Sep 30
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 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 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
$240 nightly
$267 total
Sep 28 - Sep 29
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 beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
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
$171 nightly
$192 total
Sep 7 - Sep 8
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 balcony with a round table and chairs, overlooking the beach and ocean.
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.

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
$205 nightly
$230 total
Sep 30 - Oct 1
Total with taxes and fees
Hilton Ocean City Oceanfront Suites
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A wooden console table with framed floral artwork, two lamps, and two ottomans.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.

The Oaks Waterfront

The Oaks Waterfront
Easton
$440 nightly
$484 total
Sep 2 - Sep 3
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.
View all properties

Top Eastern Shore Hotel Reviews

Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"The property definitely needs an update. We have stayed there multiple times and like the location, the pool and the pool bar. The front porch is great. The chain and deadbolt on our door didn’t work. You couldn’t set the AC to one temperature. The carpets in the whole building look like they haven’t been cleaned in years. It needs a big renovation."
Linda 4-night trip
Posted 2 hours ago
Plim Plaza Hotel
Castle in the Sand

Castle in the Sand

10/10 Excellent
"Absolutely amazing place, with two restaurants on site, being mere feet from the ocean, and the gorgeous pool. There was zero reason to leave the property. More like a resort than a hotel. Plan to make castle in the sand an annual tradition for my family!!"
Nicole 3-night trip
Posted 3 hours ago
Castle in the Sand
Coastal Palms Inn & Suites

Coastal Palms Inn & Suites

8/10 Good
"I would like a more variable breakfast and they should offer a better coffee."
Johana 3-night trip
Posted 3 hours ago
Coastal Palms Inn & Suites
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"The ocean view room was nice and is a must have. Accessibility to the boardwalk was great! It would’ve been nice if the hotel was a little more modern. Nevertheless we had a great time in Ocean City, Maryland and will be returning next year!"
Angela 3-night trip
Posted 3 hours ago
Grand Hotel Ocean City Oceanfront
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"Clean room, very short walk to the beach"
Shannon 2-night trip
Posted 7 hours ago
Days Inn by Wyndham Ocean City Oceanfront
Ashore Oceanfront Hotel by Marriott

Ashore Oceanfront Hotel by Marriott

10/10 Excellent
"Clean hotel, super easy parking, free umbrella and beach chairs. Friendly staff. We'll be back!"
PAUL 5-night trip
Posted 7 hours ago
Ashore Oceanfront Hotel by Marriott
Tidelands Caribbean Hotel and Suites

Tidelands Caribbean Hotel and Suites

10/10 Excellent
"Very clean and convenient right on the boardwalk. Recommend"
Edward 3-night trip
Posted 8 hours ago
Tidelands Caribbean Hotel and Suites
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"above being fantastic not my first time wont be our last"
Dolly 4-night trip
Posted 9 hours ago
Crystal Beach Hotel
Bonita Beach Hotel

Bonita Beach Hotel

10/10 Excellent
"Very well kept hotel clean"
Melvin 2-night trip
Posted 1 day ago
Bonita Beach Hotel

Explore a world of travel with Expedia