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 18 - Oct 19
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Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
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.
A bathroom with a toilet, a shower with a curtain, a bathtub, and a marble wall.
Exterior
A hotel room with a large bed, a flat-screen TV, a desk with a chair, and a bathroom visible through an open door.

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 marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

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 lounge chairs and umbrellas, surrounded by a fence and buildings.
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 covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

4. 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 19 - Oct 20
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.

5. 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 spacious lobby with a staircase, a reception desk, and a dining area.
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.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.

6. 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 rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

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 25 - Oct 26
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
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.

8. 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 25 - Oct 26
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A resort with a swimming pool, sun loungers, and a view of the ocean.
A fire pit in the center of a courtyard with lounge chairs and umbrellas in the background.
A beachside resort with sun loungers, umbrellas, 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.

9. 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.
$65 nightly
$73 total
Nov 4 - Nov 5
Total with taxes and fees
Holiday Inn Ocean City by IHG
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.

10. 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
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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.
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
$152 nightly
$169 total
Oct 25 - Oct 26
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
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 marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A marina with boats docked, a sandy beach, and a clear blue sky.
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 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
$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.
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 waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
$125 nightly
$139 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 Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
A hotel hallway with carpeted floors, white doors, and overhead lighting.

Hampton Inn Easton

Hampton Inn Easton
Easton
$128 nightly
$141 total
Nov 8 - Nov 9
Total with taxes and fees
Hampton Inn Easton
Exterior
Pool
A modern hotel building with a 'HOME 2' sign, multiple flags, and a covered entrance.
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 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 living room with a beige sofa, blue and red patterned pillows, a wooden coffee table, and a view of the ocean through large windows.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
$81 nightly
$91 total
Nov 1 - Nov 2
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 marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A marina with boats docked, a sandy beach, and a clear blue sky.
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 swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
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 living room with a beige sofa, blue and red patterned pillows, a wooden coffee table, and a view of the ocean through large windows.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
$81 nightly
$91 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 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
$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.
A balcony with a round table and chairs, overlooking the beach and ocean.
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.

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 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.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

The Oaks Waterfront

The Oaks Waterfront
Easton
$489 nightly
$538 total
Oct 19 - Oct 20
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

The Americana Hotel

The Americana Hotel

10/10 Excellent
"Great stay! A+ service, will book again."
Carolyn 3-night trip
Posted 1 hour ago
The Americana Hotel
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"This is an older building by the ocean, so it may not be the fanciest place. But it is well-maintained and clean. The staff are very friendly, helpful, and, perhaps most importantly, everyone had a great attitude. It is a dog friendly hotel and it shows. They have a nice grassy area with a faux fire hydrant and bags to make it easy to clean up after your dog. I will stay here again."
Ginny 3-night trip
Posted 14 hours ago
Days Inn by Wyndham Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

8/10 Good
"Great place for a couples getaway or a whole family"
Ashley 1-night trip
Posted 15 hours ago
Princess Royale Oceanfront Resort
Castle in the Sand

Castle in the Sand

10/10 Excellent
"Nice location. Has an outdoor bar. Hair drier did not work but only stayed 1 night. Perhaps they would have corrected it.Iron worked fine. Furniture is outdated but ok of you don’t want luxury. Lo ed the bed and pillows."
Brian 1-night trip
Posted 18 hours ago
Castle in the Sand
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"Huge busy hotel, well maintained. Booked oceanfront room with jetted tub, and it was amazing. Located right on the boardwalk, super convenient. Parking is $10/night across the street."
Elena 2-night trip
Posted 23 hours ago
Grand Hotel Ocean City Oceanfront
Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"Nice place to stay. Clean but dated. Shower took a long time to warm up."
John D 3-night trip
Posted 2 days ago
Plim Plaza Hotel
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 2 days ago
St Michaels Inn

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