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 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Eastern Shore hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
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.

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.
$105 nightly
$117 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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.

2. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Aquatic paradise awaits with 2 outdoor pools, indoor pool, and waterslide offering year-round relaxation at this riverside resort.
$171 nightly
$194 total
Nov 18 - Nov 19
Total with taxes and fees
Hyatt Regency Chesapeake Bay
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A bathroom with a toilet, a shower with a curtain, a bathtub, and a marble wall.
A snack and beverage section with shelves stocked with various snacks and a refrigerator with bottled drinks.
A wooden pavilion with picnic tables and benches, a grill, and a red bench.

3. 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.
$90 nightly
$100 total
Nov 8 - Nov 9
Total with taxes and fees
Best Western Kent Narrows Inn
An indoor swimming pool with clear views of boats and water.
A balcony with a view of a marina and row houses.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A balcony with a view of a body of water, a row of buildings, and a chair.

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.
$125 nightly
$138 total
Nov 18 - Nov 19
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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.

5. 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 22 - Oct 23
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 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.
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.
$110 nightly
$122 total
Oct 28 - Oct 29
Total with taxes and fees
Comfort Inn & Suites Cambridge
A spacious lobby with a staircase, a reception desk, and a dining area.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
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.

7. 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.
$83 nightly
$93 total
Nov 15 - Nov 16
Total with taxes and fees
Quality Inn Grasonville near Kent Island
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
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.

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.
$149 nightly
$165 total
Nov 18 - Nov 19
Total with taxes and fees
Hyatt Place Kent Narrows & 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 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.

9. 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.
$119 nightly
$131 total
Nov 15 - Nov 16
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A large indoor swimming pool with wooden beams, white walls, and lounge chairs along the sides.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.
A balcony with wicker furniture overlooking a beach.
A beach chair under a blue umbrella on a sandy beach with the ocean in the background.

10. Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
  • Oceanfront indoor pool sanctuary with modern loungers and beach yoga classes creates a perfect aquatic escape any season.
$57 nightly
$63 total
Nov 10 - Nov 11
Total with taxes and fees
Hilton Garden Inn 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

Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
A reception desk with a modern design, a digital display, and a check-in counter.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
$105 nightly
$117 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Room
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A restaurant with a counter, seating area, and a clock on the wall.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
$90 nightly
$100 total
Nov 8 - Nov 9
Total with taxes and fees
Best Western Kent Narrows Inn
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
$171 nightly
$194 total
Nov 18 - Nov 19
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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
$89 nightly
$98 total
Oct 22 - Oct 23
Total with taxes and fees
Baymont by Wyndham Easton
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A spacious dining area with multiple tables and chairs, large windows offering a view of the ocean, and a modern interior design.
A beach chair under a blue umbrella on a sandy beach with the ocean in the background.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
$57 nightly
$63 total
Nov 10 - Nov 11
Total with taxes and fees
Hilton Garden Inn Ocean City Oceanfront
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".
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.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
$110 nightly
$122 total
Oct 28 - Oct 29
Total with taxes and fees
Comfort Inn & Suites Cambridge
A patio with outdoor seating, overlooking a marina with boats.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.
An indoor swimming pool with clear views of boats and water.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
$125 nightly
$138 total
Nov 18 - Nov 19
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A spacious lobby with a staircase, a reception desk, and a dining area.

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
$83 nightly
$93 total
Nov 15 - Nov 16
Total with taxes and fees
Quality Inn Grasonville near Kent Island
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 lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

Hampton Inn Easton

Hampton Inn Easton
Easton
$128 nightly
$141 total
Oct 29 - Oct 30
Total with taxes and fees
Hampton Inn Easton
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.
A hotel with a covered entrance, multiple floors, and a parking lot.
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135 nightly
$149 total
Nov 1 - Nov 2
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
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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 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
$171 nightly
$194 total
Nov 18 - Nov 19
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 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 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
$81 nightly
$91 total
Nov 2 - Nov 3
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
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.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
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
$115 nightly
$129 total
Nov 1 - Nov 2
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 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 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
$237 nightly
$263 total
Nov 15 - Nov 16
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 wooden console table with framed floral artwork, two lamps, and two ottomans.
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
Oct 22 - Oct 23
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
"Everything was above what you would expect, staff, clean room, balcony and beach view!!😎😎"
David J. 4-night trip
Posted 2 hours ago
Holiday Inn & Suites Ocean City by IHG
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"It was good"
Thomas 2-night trip
Posted 3 hours ago
Grand Hotel Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Nice hotel, onsite restaurant and bars, right on the beach which was perfect and parking is easy to get to."
Jennifer 1-night trip
Posted 4 hours ago
Princess Royale Oceanfront Resort
Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"Todo muy bien"
Ana 3-night trip
Posted 8 hours ago
Plim Plaza Hotel
The Americana Hotel

The Americana Hotel

8/10 Good
"The only problem I had with this stay was Ac was not that cold but other than that everything was fine."
Deandre 3-night trip
Posted 1 day ago
The Americana Hotel
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"Great area to stay in plenty of great places to eat in walking distance and an excellent room with amazing room service"
Liam 3-night trip
Posted 3 days ago
Crystal Beach Hotel

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