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
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
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.
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.

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.
$103 nightly
$114 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 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.
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 27 - Sep 28
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 covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
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.

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 27 - Sep 28
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 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.

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 lobby with green sofas, a round table with a plant, and a lantern.
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.

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.
$79 nightly
$89 total
Oct 25 - Oct 26
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 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.
A beachfront hotel with multiple floors, balconies, and a large glass facade.

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 lounge area with multiple seating arrangements, including sofas and chairs, a central wooden planter, and ambient lighting.
A modern house with a glass door entrance, outdoor seating area with chairs, and a small table.
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 waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

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 4 - Oct 5
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 castle-like building with a swimming pool, surrounded by trees and illuminated by street lights.
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 beachside restaurant with outdoor seating and umbrellas.

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 28 - Sep 29
Total with taxes and fees
Castle in the Sand
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

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 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.
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 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 with a brick facade, multiple parking spaces, and a landscaped area with trees.
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 27 - Sep 28
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
$152 nightly
$169 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.
A modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A reception area with two reception desks, a wall-mounted sign reading "Holiday Inn Express," and a telephone on the right side.

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
Easton
$134 nightly
$147 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Easton by IHG
A spacious lobby with a reception desk, seating area, and a television screen.
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.
A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

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 hotel room with two beds, a desk, a TV, a chair, and a large window with curtains.
A spacious lobby with a mix of seating options, including sofas and chairs, and a bar area with stools.
A modern hotel room with a kitchenette, a large mirror, a flat-screen TV, and a sofa.

Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland
Fruitland
$122 nightly
$137 total
Oct 4 - Oct 5
Total with taxes and fees
Hampton Inn & Suites Salisbury/Fruitland
A modern lobby with a reception desk, seating area, and artwork on the walls.
A modern restaurant with booths and tables, a kitchen area, and a large window.
A hotel room with a bed, a sofa, a TV, a desk, and a large window.

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City
Pocomoke City
$127 nightly
$142 total
Sep 29 - Sep 30
Total with taxes and fees
Best Western Plus Pocomoke City
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.
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
$99 nightly
$109 total
Sep 27 - Sep 28
Total with taxes and fees
Baymont by Wyndham Easton
A swimming pool with a metal ladder, lounge chairs, and a small building in the background.
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.
A hotel lobby with a reception desk, seating area, and a large wall mural.

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
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with high ceilings, large windows, and modern chandeliers.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

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
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 high ceilings, large windows, and modern chandeliers.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

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 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.
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.

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
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 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.

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 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 banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

The Oaks Waterfront

The Oaks Waterfront
Easton
$489 nightly
$538 total
Sep 27 - Sep 28
Total with taxes and fees
The Oaks Waterfront
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 beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
$98 nightly
$109 total
Oct 12 - Oct 13
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
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

10/10 Excellent
"Great place to stay!"
Phyllis 2-night trip
Posted 2 hours ago
Plim Plaza Hotel
Bonita Beach Hotel

Bonita Beach Hotel

10/10 Excellent
"Property is clean. Helpful staff. Fridge and microwave. Parking spaces tight for SUVs but plenty of street parking."
Juan 2-night trip
Posted 4 hours ago
Bonita Beach Hotel
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

10/10 Excellent
"I love the this hotel come here every year this year 3 times staff is always happy cheerful an friendly beds are comfy so much close by an it’s right on the beach"
Amy 1-night trip
Posted 16 hours ago
Carousel Resort Hotel & Condominiums
Fenwick Inn

Fenwick Inn

8/10 Good
"I had a nice stay at the fenwick inn, it was a great value, but the hotel is somewhat old and even with renovations it still shows its age"
John 2-night trip
Posted 18 hours ago
Fenwick Inn
Quality Inn Oceanfront

Quality Inn Oceanfront

10/10 Excellent
"The place had a great elevator super fast, close to the beach, nice hot tubs (2) which they changed the water every day nice, the inside pool was a little cold maybe a heater, the outside pool looked nice but the weather sucked really bad so we didn't get to use it oh well not their fault the staff was nice good free coffee and tea pretty good parking, the tropical birds were cool fish, and turtles too. All in all pretty nice would stay again hopefully with better weather. Thanks."
mark 5-night trip
Posted 18 hours ago
Quality Inn Oceanfront
Comfort Suites Ocean City West

Comfort Suites Ocean City West

8/10 Good
"The only thing was the tub looked so bad dirty stains"
alan 2-night trip
Posted 19 hours ago
Comfort Suites Ocean City West
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"My young family of 4 stayed for only one night mid September. We used the private beach and also the indoor pool. Having access to that private beach was the main reason we decided to stay here. The facilities and room are a bit run down but comfortable enough."
Lynn 1-night trip
Posted 22 hours ago
Princess Bayside Beach Hotel
Crystal Beach Hotel

Crystal Beach Hotel

8/10 Good
"This property smelled so clean would love to know what cleaning solutions they are using."
Victoria 1-night trip
Posted 1 day ago
Crystal Beach Hotel

Explore a world of travel with Expedia