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 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Eastern Shore hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
A modern food court with a central island, various food stations, and a yogurt display.
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.
$110 nightly
$122 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 gym with a treadmill, elliptical, and stationary bike.
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.

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.
$89 nightly
$98 total
Oct 7 - Oct 8
Total with taxes and fees
Baymont by Wyndham Easton
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 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.

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
Oct 7 - Oct 8
Total with taxes and fees
Best Western Plus Easton Inn & Suites
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A bathroom with a glass-enclosed shower, a white toilet, and a white sink.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.
A restaurant with a counter, seating area, and a clock on the wall.

4. 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 13 - Oct 14
Total with taxes and fees
Best Western Kent Narrows 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 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.

5. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$112 nightly
$124 total
Nov 3 - Nov 4
Total with taxes and fees
Comfort Inn & Suites Cambridge
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.

6. 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
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.
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.

7. 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 resort with a swimming pool, sun loungers, 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 dining area with a long table and six chairs, a grill, and potted plants.
A beachside resort with sun loungers, umbrellas, and a view of the ocean.

8. 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 4 - Nov 5
Total with taxes and fees
Holiday Inn Ocean City by IHG
An indoor swimming pool with clear views of boats and water.
A patio with outdoor seating, overlooking a marina with boats.
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.

9. 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 swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
A balcony with a view of the ocean and beach.
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.

10. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
  • Plunge into ocean views at this beachfront hotel with 3 pools, where sun-drenched relaxation meets poolside cocktail service.
$89 nightly
$100 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
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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 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
Two Adirondack chairs facing a calm body of water with a clear sky above.
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 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
$110 nightly
$122 total
Oct 25 - Oct 26
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 modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
Marina
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 sandy beach, and a clear blue sky.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$203 nightly
$231 total
Nov 4 - Nov 5
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
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
Oct 7 - Oct 8
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
A hotel hallway with carpeted floors, white doors, and overhead lighting.
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 18 - Oct 19
Total with taxes and fees
Hampton Inn 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
$112 nightly
$124 total
Nov 3 - Nov 4
Total with taxes and fees
Comfort Inn & Suites Cambridge
A hotel room with a large bed, a desk with a lamp, a chair, a dresser, and a large window with curtains.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
A balcony with a round table and chairs, overlooking the beach and ocean.

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
$111 nightly
$124 total
Nov 3 - Nov 4
Total with taxes and fees
Hilton Ocean City Oceanfront Suites
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.
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 7 - Oct 8
Total with taxes and fees
Baymont by Wyndham Easton
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
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.
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
$89 nightly
$100 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
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 spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$203 nightly
$231 total
Nov 4 - Nov 5
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 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.
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
$89 nightly
$100 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
A hotel room with a large bed, a desk with a lamp, a chair, a dresser, and a large window with curtains.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
A balcony with a round table and chairs, overlooking the beach and ocean.

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
$111 nightly
$124 total
Nov 3 - Nov 4
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 bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

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 deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
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 7 - Oct 8
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

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"Room was very clean . I like that the floor isn’t carpeted."
Mary E 2-night trip
Posted 2 hours ago
Grand Hotel Ocean City Oceanfront
Castle in the Sand

Castle in the Sand

10/10 Excellent
"The bathroom was clean but a little in need of upgrades. The hotel staff were amazing so helpful and nice! Great location!"
Katherine 3-night trip
Posted 18 hours ago
Castle in the Sand
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

8/10 Good
"The room over"
Ken 2-night trip
Posted 21 hours ago
Carousel Resort Hotel & Condominiums
The Shore House

The Shore House

8/10 Good
"Quick one night stay before checking into our boardwalk hotel for the week. Clean small room with everything needed for one night. Easy check in and friendly staff. Would recommend for sure!"
Bree 1-night trip
Posted 2 days ago
The Shore House
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 5 days ago
St Michaels Inn

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