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 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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 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.

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 27 - Sep 28
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 27 - Sep 28
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.
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.

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 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 beachfront hotel with multiple floors, balconies, and a large glass facade.
A balcony with a view of the ocean, featuring a railing and blue chairs.

5. 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
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 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.
$115 nightly
$127 total
Sep 30 - Oct 1
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 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.

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.
$79 nightly
$89 total
Oct 25 - Oct 26
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A bathroom with a bathtub, toilet, and shower.
A kitchenette with a coffee machine, a framed picture, and a potted plant.
A hotel room with two beds, a desk, a chair, and a television.

8. 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.
$127 nightly
$141 total
Oct 4 - Oct 5
Total with taxes and fees
Best Western Kent Narrows Inn
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.
A hotel room with a large bed, a desk, a chair, and a view of the city through large windows.
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.

9. 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.
$110 nightly
$123 total
Oct 5 - Oct 6
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 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.

10. 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
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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 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 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.

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 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 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.
An outdoor event area with round tables and a view of the water.

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 reception area with two reception desks, a wall-mounted sign reading "Holiday Inn Express," and a telephone on the right side.
A Holiday Inn Express sign with a green and blue logo, surrounded by landscaped garden beds and trimmed hedges.
A coffee station with two coffee machines and a variety of coffee pods and cups.

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 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.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
$115 nightly
$127 total
Sep 30 - Oct 1
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 hotel room with two beds, a desk, a TV, a chair, and a large window with curtains.

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 hotel room with a large bed, bedside lamps, a nightstand, a window with blinds, and a wall-mounted abstract painting.
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
Sep 28 - Sep 29
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 kitchen with a stone wall, a microwave, and various food items on the counter.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.
A residential area with a large building, a swimming pool, and well-maintained lawns.

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 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.
A restaurant with a bar area, seating, and a kitchen in the background.

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 sandy beach, and a clear blue sky.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$245 nightly
$278 total
Oct 6 - Oct 7
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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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 sandy beach, and a clear blue sky.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$245 nightly
$278 total
Oct 6 - Oct 7
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 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.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina 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 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
$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 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 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 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
$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.
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Top Eastern Shore Hotel Reviews

Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"Accessibility to beach and main attractions on boardwalk"
Heather 3-night trip
Posted 6 hours ago
Plim Plaza Hotel
Crystal Beach Hotel

Crystal Beach Hotel

8/10 Good
"Good time"
Wendy 4-night trip
Posted 6 hours ago
Crystal Beach Hotel
Fenwick Inn

Fenwick Inn

10/10 Excellent
"This is one of the best hotels in the city. Good customer service and spacious rooms. We stayed for 3 days and enjoyed our stay at the hotel. They also have a beautuful rooftop restaurant with a city view. A good place for short or long term stay."
manisha 3-night trip
Posted 12 hours ago
Fenwick Inn
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

10/10 Excellent
"I love the beach view so nice to watch the water"
susan 2-night trip
Posted 17 hours ago
Carousel Resort Hotel & Condominiums
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

8/10 Good
"Very clean, bedding, floors, bath Excellent beach view. Would stay here again"
John 2-night trip
Posted 2 days ago
Days Inn by Wyndham Ocean City Oceanfront
Francis Scott Key Family Resort

Francis Scott Key Family Resort

10/10 Excellent
"Great place for kids to have fun and enjoy a vacation. It was close to everything and the food onsite was good. The room was beautifully clean and comfortable. Would definitely stay again. Thank you."
Rosemary 2-night trip
Posted 2 days ago
Francis Scott Key Family Resort
Comfort Inn Gold Coast

Comfort Inn Gold Coast

10/10 Excellent
"Hotel is very clean, room was very clean and comfortable. Great area."
Patrick 2-night trip
Posted 3 days ago
Comfort Inn Gold Coast

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