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 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Eastern Shore hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.
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.
$105 nightly
$117 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A resort with a large pool, outdoor seating, and a view of the sea.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious restaurant with high ceilings, large windows, and a variety of seating arrangements.

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.
$169 nightly
$192 total
Nov 23 - Nov 24
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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 patio with outdoor seating, overlooking a marina with boats.

3. 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.
$131 nightly
$146 total
Nov 22 - Nov 23
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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 rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

4. 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.
$139 nightly
$154 total
Nov 24 - Nov 25
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A residential area with a large building, a swimming pool, and well-maintained lawns.
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 room with a large bed, a desk, a chair, a television, and a window with curtains.

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.
$90 nightly
$99 total
Nov 2 - Nov 3
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 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.

6. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$108 nightly
$120 total
Nov 22 - Nov 23
Total with taxes and fees
Comfort Inn & Suites Cambridge
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
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.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

7. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$80 nightly
$88 total
Nov 24 - Nov 25
Total with taxes and fees
St Michaels Inn
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.
A gym with exercise equipment, a bench, and a wall-mounted mirror.
Exterior

8. 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
A spacious lobby with a staircase, a reception desk, and a dining area.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
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.

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.
$84 nightly
$93 total
Nov 22 - Nov 23
Total with taxes and fees
Quality Inn Grasonville near Kent Island
A resort with a swimming pool, sun loungers, and a view of the ocean.
A restaurant interior with brick walls, wooden tables, and shelves of wine bottles.
A beachside resort with sun loungers, umbrellas, and a view of the ocean.
A hotel entrance with a stone facade, a green-lit wall, and a variety of tropical plants.

10. 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.
$61 nightly
$68 total
Nov 24 - Nov 25
Total with taxes and fees
Holiday Inn Ocean City by IHG
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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 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 buffet with various food items, including omelets and baked goods, served in metal containers.

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
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.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
$139 nightly
$154 total
Nov 24 - Nov 25
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.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
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
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 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.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
$108 nightly
$120 total
Nov 22 - Nov 23
Total with taxes and fees
Comfort Inn & Suites Cambridge
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 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
$119 nightly
$131 total
Nov 15 - Nov 16
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 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.
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
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
$81 nightly
$91 total
Nov 2 - Nov 3
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
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.
A kitchen with a stone wall, a microwave, and various food items on the counter.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
$90 nightly
$99 total
Nov 2 - Nov 3
Total with taxes and fees
Baymont by Wyndham Easton
A multi-story hotel with balconies, located near a waterfront.
A modern bar area with a circular counter, bar stools, and a seating area with a view of bicycles outside.
A dining area with a table set for two, potted plants, and a view through large windows.
A balcony with white railings and orange chairs, overlooking a body of water and a distant shoreline.

Cambria Hotel Ocean City - Bayfront

Cambria Hotel Ocean City - Bayfront
Downtown Ocean City
$97 nightly
$108 total
Nov 16 - Nov 17
Total with taxes and fees
Cambria Hotel Ocean City - Bayfront
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.
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
$131 nightly
$146 total
Nov 22 - Nov 23
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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4-star hotels with pools in Eastern Shore

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
$81 nightly
$91 total
Nov 2 - Nov 3
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
A resort with a large pool, outdoor seating, and a view of the sea.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious restaurant with high ceilings, large windows, and a variety of seating arrangements.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$169 nightly
$192 total
Nov 23 - Nov 24
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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 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.

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
$115 nightly
$129 total
Nov 2 - Nov 3
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 balcony with a view of a marina filled with boats.
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.

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 banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
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 27 - Oct 28
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

Castle in the Sand

Castle in the Sand

10/10 Excellent
"Always a good stay in OC"
Anthony 2-night trip
Posted 2 hours ago
Castle in the Sand
The Americana Hotel

The Americana Hotel

10/10 Excellent
"Very clean and well maintained"
Matt 2-night trip
Posted 10 hours ago
The Americana Hotel
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

10/10 Excellent
"Excellent location and services"
Emmanuel 1-night trip
Posted 14 hours ago
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel
Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG

10/10 Excellent
"Emily was her usual sweet and extremely helpful self."
Dan 4-night trip
Posted 17 hours ago
Holiday Inn Ocean City by IHG
Quality Inn Oceanfront

Quality Inn Oceanfront

8/10 Good
"Heat wasn't working the first nite , it was cold , maintenance fixed it but it stopped working again over nite the second nite ."
David 2-night trip
Posted 17 hours ago
Quality Inn Oceanfront
Comfort Suites Ocean City West

Comfort Suites Ocean City West

8/10 Good
"Nice hotel but the plug in air freshener in the room was overwhelming strong. We ended up unplugging it but that did not help so we put it outside the room."
Barbara 2-night trip
Posted 19 hours ago
Comfort Suites Ocean City West
Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"Clean property with friendly staff"
Kathryn 1-night trip
Posted 19 hours ago
Holiday Inn & Suites Ocean City by IHG
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"I loved this resort. Food was good"
Jamie 4-night trip
Posted 1 day ago
Princess Royale Oceanfront Resort
Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"The staff was amazing…we added a night and Renae(desk) and Draymond(night manager) were very helpful in combining our reservations so we didn’t have to change rooms the next day. They were both very helpful…it’s how changes should work. Thank you both."
Alan 1-night trip
Posted 2 days ago
Plim Plaza Hotel

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