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
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
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.
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 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.
$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 hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.
Exterior
A gym with exercise equipment, a bench, and a wall-mounted mirror.

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 covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
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
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 spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A patio with outdoor seating, overlooking a marina with boats.

4. 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.
$139 nightly
$154 total
Oct 19 - Oct 20
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
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 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 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".

6. 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 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 dining area with a long table and six chairs, a grill, and potted plants.
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.
$66 nightly
$74 total
Nov 2 - Nov 3
Total with taxes and fees
Holiday Inn Ocean City by IHG
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.

8. 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 pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
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.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

9. 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
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.
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.

10. 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 11 - Oct 12
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
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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

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 modern food court with a central island, various food stations, and a yogurt display.
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
$103 nightly
$114 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.
A wooden pavilion with picnic tables and benches, a grill, and a red bench.
A gym with exercise equipment, a bench, and a wall-mounted mirror.
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
$108 nightly
$120 total
Oct 4 - Oct 5
Total with taxes and fees
Best Western Kent Narrows Inn
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 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.

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 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 13 - Oct 14
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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 spacious dining area with high ceilings, large windows, and modern chandeliers.
A marina with boats docked, a sandy beach, and a clear blue sky.

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 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 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.

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 hotel dining area with a long table, four chairs, and three pendant lights.
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

Hampton Inn Easton

Hampton Inn Easton
Easton
$128 nightly
$141 total
Oct 11 - Oct 12
Total with taxes and fees
Hampton Inn Easton
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 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 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 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.

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
A patio with outdoor seating, overlooking a marina with boats.
An indoor swimming pool with clear views of boats and water.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
$139 nightly
$154 total
Oct 19 - Oct 20
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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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 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 high ceilings, large windows, and modern chandeliers.
A marina with boats docked, a sandy beach, and a clear blue sky.

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 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 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 hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
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 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
$111 nightly
$124 total
Nov 1 - Nov 2
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 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 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
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

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"I would rate the hotel, the room and the staff 6 stars if I could. The room was very clean and comfortable. The room was super quiet. It’s really one of the nicest hotel rooms I’ve ever stayed in. The HVAC system was silent and kept the temperature very comfortable. Even the bed was amazing. Finally a mattress that was long enough so my feet didn’t hang over the edge. The balcony was large and the view was fantastic. We cooked breakfast in the well stocked kitchen, and ate on the balcony every morning. The dishwasher made clean up easy. All appliances were modern and worked perfectly. We didn’t use the hot tub but it was there if we wanted to. I really can’t think of anything negative except that we had to leave to go home. What a nice place."
John 3-night trip
Posted less than an hour ago
Holiday Inn & Suites Ocean City by IHG
Castle in the Sand

Castle in the Sand

8/10 Good
"Resort type hotel right on the beach happy hour with rock band playing on a Monday afternoon, Good value for money spent easy parking,"
James 1-night trip
Posted 2 hours ago
Castle in the Sand
Quality Inn Oceanfront

Quality Inn Oceanfront

10/10 Excellent
"Fantastic as always. My only mild complaint is I wish they'd update their showers. Water pressure wasn't great and neither was the temperature control. HOWEVER I love this hotel. The staff is wonderful, rooms are a good size, great view from the ocean front side and my family LOVES the birds. Fantastic deal for the price."
Abbey 1-night trip
Posted 5 hours ago
Quality Inn Oceanfront
Bonita Beach Hotel

Bonita Beach Hotel

10/10 Excellent
"Clean rooms. Clean property."
Joshua 4-night trip
Posted 6 hours ago
Bonita Beach Hotel
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"Everything was great, front desk was very helpful"
Hilda 1-night trip
Posted 11 hours ago
Crystal Beach Hotel
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 1 day 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

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