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

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Oct 1 - Oct 2
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Oct 2 - Oct 3
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Oct 2 - Oct 4
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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 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
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A snack and beverage section with shelves stocked with various snacks and a refrigerator with bottled drinks.
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.
A bathroom with a bathtub, toilet, and a shower area.

2. 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 4 - Oct 5
Total with taxes and fees
Best Western Kent Narrows Inn
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 gym with a treadmill, elliptical, and stationary bike.
A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.

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.
$89 nightly
$98 total
Oct 4 - Oct 5
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 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.
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.
$113 nightly
$125 total
Oct 27 - Oct 28
Total with taxes and fees
Comfort Inn & Suites Cambridge
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.
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 spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

5. 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
Oct 4 - Oct 5
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A poolside area with blue lounge chairs and yellow umbrellas, a sign for Grand Hotel, and palm trees in the background.
A beachfront hotel with multiple balconies overlooking the ocean.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.
A lobby with green sofas, a round table with a plant, and a lantern.

6. 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.
$67 nightly
$75 total
Nov 1 - Nov 2
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.

7. 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.
$74 nightly
$83 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Ocean City by IHG
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
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.

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 13 - Oct 14
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A spacious lobby with a staircase, a reception desk, and a dining area.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A hotel room with a bed, a sofa, a desk, and two chairs. There are two lamps on the desk and a picture frame on the wall.

9. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
  • Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
$96 nightly
$107 total
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Grasonville near Kent Island
An indoor swimming pool with clear views of boats and water.
A balcony with a view of a body of water, a row of buildings, and a chair.
A balcony with a view of a marina and row houses.
A patio with outdoor seating, overlooking a marina with boats.

10. 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 12 - Oct 13
Total with taxes and fees
Hilton Garden Inn Kent Island 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 with a brick facade, multiple parking spaces, and a landscaped area with trees.
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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$129 nightly
$142 total
Oct 4 - Oct 5
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 modern food court with a central island, various food stations, and a yogurt display.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
$103 nightly
$114 total
Nov 1 - Nov 2
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.
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.
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 13 - Oct 14
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.
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
Oct 11 - Oct 12
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 gym with a treadmill, elliptical, and stationary bike.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
$89 nightly
$98 total
Oct 4 - Oct 5
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 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.
A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
$113 nightly
$125 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 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.
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
$106 nightly
$118 total
Nov 1 - Nov 2
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 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.
An indoor swimming pool with clear blue water, surrounded by lounge chairs and tables.

Country Inn & Suites by Radisson, Salisbury, MD

Country Inn & Suites by Radisson, Salisbury, MD
Salisbury
$89 nightly
$99 total
Nov 1 - Nov 2
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 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.
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
$114 nightly
$127 total
Nov 1 - Nov 2
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 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.
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
$111 nightly
$124 total
Nov 1 - Nov 2
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 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
$242 nightly
$275 total
Oct 27 - Oct 28
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 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.

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 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
$89 nightly
$100 total
Nov 1 - Nov 2
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 white colonial-style house with a covered porch, brick steps, and outdoor seating.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

The Oaks Waterfront

The Oaks Waterfront
Easton
$489 nightly
$538 total
Oct 4 - Oct 5
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

Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

10/10 Excellent
"My sister in law and I spent Sept 21-26 2026 for a girls trip. We were pleased with our ocean front balcony room and appreciated having the restaurant, indoor pool and hot tub on premises. We were there during the Sept nor'easter so not having to leave the hotel to eat was very nice. All the staff were polite and friendly. We plan to come again hoping to be able to enjoy the beach next time."
Teresa 4-night trip
Posted 14 hours ago
Carousel Resort Hotel & Condominiums
Francis Scott Key Family Resort

Francis Scott Key Family Resort

8/10 Good
"Great place for families lots of amenities to keep them entertained"
Reyna 2-night trip
Posted 2 days ago
Francis Scott Key Family Resort
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 3 days ago
Bonita Beach Hotel

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