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 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
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.
Two Adirondack chairs facing a calm body of water with a clear sky above.

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 8 - Nov 9
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.
Room
A bathroom with a toilet, a shower with a curtain, a bathtub, and a marble wall.
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.
$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 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 spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.

3. 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
A swimming pool with a 5ft depth marker, white lounge chairs, and tables arranged around the pool area.
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".

4. 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 27 - Oct 28
Total with taxes and fees
Comfort Inn & Suites Cambridge
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 hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.

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 20 - Oct 21
Total with taxes and fees
Baymont by Wyndham Easton
A large indoor swimming pool with wooden beams, white walls, and lounge chairs along the sides.
A beach chair under a blue umbrella on a sandy beach with the ocean in the background.
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A balcony with wicker furniture overlooking a beach.

6. 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.
$65 nightly
$73 total
Nov 8 - Nov 9
Total with taxes and fees
Hilton Garden Inn Ocean City Oceanfront
An indoor swimming pool with clear views of boats and water.
A balcony with a view of a marina and row houses.
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.

7. 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 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.

8. 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.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
An outdoor event area with round tables and a view of the water.

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 26 - Oct 27
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.
A hotel room with two beds, a chair, and a painting on the wall.

10. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$81 nightly
$89 total
Nov 19 - Nov 20
Total with taxes and fees
St Michaels 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

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

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
$105 nightly
$117 total
Nov 8 - Nov 9
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.
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.
Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
$152 nightly
$169 total
Oct 26 - Oct 27
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A hotel room with a large bed, a desk, a television, and a desk lamp.
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.
A hotel with a covered entrance, multiple floors, and a parking lot.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135 nightly
$149 total
Oct 25 - Oct 26
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
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 spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.

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 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 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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$119 nightly
$131 total
Nov 15 - Nov 16
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A balcony with two green Adirondack chairs facing a beach.
A hotel room with two beds, a desk, and a chair. There is a window with curtains, a lamp, and a nightstand with a phone.
A beach view from a balcony with a clear sky.
A restaurant with multiple round tables and chairs, a flat-screen TV mounted on the wall, and a window with an umbrella.

Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk
Downtown Ocean City
$67 nightly
$75 total
Nov 18 - Nov 19
Total with taxes and fees
Comfort Inn Ocean City Boardwalk
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.
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.

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 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 hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

Hampton Inn Easton

Hampton Inn Easton
Easton
$128 nightly
$141 total
Oct 29 - Oct 30
Total with taxes and fees
Hampton Inn Easton
Pool
Terrace/patio
A hotel reception area with a wooden reception desk, a blue chair, and a red chair.
A modern hotel lobby with seating areas, a television, and a snack bar.

Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland
Fruitland
$105 nightly
$118 total
Nov 9 - Nov 10
Total with taxes and fees
Home2 Suites By Hilton Salisbury Fruitland
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 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 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
$81 nightly
$91 total
Nov 3 - Nov 4
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
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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 spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.

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 swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
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 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
$81 nightly
$91 total
Nov 3 - Nov 4
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 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
$237 nightly
$263 total
Nov 15 - Nov 16
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 dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.
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 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 20 - Oct 21
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

8/10 Good
"We found our room to be surprisingly spacious, very clean, and comfortable; however, the kitchenette/bathroom areas were a bit dated. The property location was excellent and there were restaurants and a pool within the property. The common areas inside the hotel and the outdoor space at the front of the hotel were adequate, but guests were somewhat disrespectful, leaving their trash, not replacing chairs after their use, etc... The staff was pleasant enough when checking-in and helpful when we had a question but were ignoring simple tasks like straightening up the common areas when time allowed. Although this was a little off-putting, we would return if the opportunity presented itself."
Keli 1-night trip
Posted 1 hour ago
Grand Hotel Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"The property was very clean, staff was awesome and overall the experience was amazing."
Shy 1-night trip
Posted 6 hours ago
Princess Royale Oceanfront Resort
Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"Comfortable bed. Good location."
Alexander 1-night trip
Posted 8 hours ago
Plim Plaza Hotel
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Great location. Very clean."
scott 2-night trip
Posted 8 hours ago
St Michaels Inn
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"Clean room, friendly staff and great view."
Jill 2-night trip
Posted 9 hours ago
Days Inn by Wyndham Ocean City Oceanfront
The Americana Hotel

The Americana Hotel

10/10 Excellent
"Everything is wonderful! Our family love this place and we will be back."
Arriya 1-night trip
Posted 9 hours ago
The Americana Hotel
Quality Inn Oceanfront

Quality Inn Oceanfront

10/10 Excellent
"Nic clean room"
Tim 1-night trip
Posted 13 hours ago
Quality Inn Oceanfront

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