A marina with numerous boats docked at wooden piers under a clear sky.

Find Hotels with a Pool in Eastern Shore, MD from CA $102

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Check availability on Eastern Shore Hotels with a Pool

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
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 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 modern food court with a central island, various food stations, and a yogurt display.

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.
CA $148
CA $164 total
includes taxes & fees
Nov 15 - Nov 16
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 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.
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.
CA $227
CA $298 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
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 snack and beverage section with shelves stocked with various snacks and a refrigerator with bottled drinks.

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.
CA $126
CA $140 total
includes taxes & fees
Nov 16 - Nov 17
Best Western Kent Narrows Inn
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.
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.

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.
CA $214
CA $237 total
includes taxes & fees
Oct 29 - Oct 30
Hyatt Place Kent Narrows & Marina
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
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.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

5. 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.
CA $191
CA $210 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield Inn & Suites by Marriott 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 room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.

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.
CA $91
CA $102 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Ocean City Oceanfront
A swimming pool with a 5ft depth marker, white lounge chairs, and tables arranged around the pool area.
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.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

7. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
CA $155
CA $172 total
includes taxes & fees
Oct 26 - Oct 27
Comfort Inn & Suites Cambridge
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
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.
A gym with a treadmill, elliptical, and stationary bike.

8. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.
CA $125
CA $138 total
includes taxes & fees
Oct 22 - Oct 23
Baymont by Wyndham Easton
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 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.

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.
CA $118
CA $131 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Grasonville near Kent Island
A poolside area with blue lounge chairs and yellow umbrellas, a sign for Grand Hotel, and palm trees in the background.
A lobby with green sofas, a round table with a plant, and a lantern.
A hotel room with two beds, a balcony, a dining area, and a view of the city.
A beachfront hotel with multiple balconies overlooking the ocean.

10. Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
  • Float in indoor or outdoor pools with oceanfront views in this beach retreat.
CA $91
CA $101 total
includes taxes & fees
Nov 2 - Nov 3
Grand Hotel 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 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 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.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
CA $148
CA $164 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
Room
A poolside area with lounge chairs and a mural of a sunset over water.
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.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
CA $126
CA $140 total
includes taxes & fees
Nov 16 - Nov 17
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 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.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
CA $227
CA $298 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
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 gym with a treadmill, elliptical, and stationary bike.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
CA $125
CA $138 total
includes taxes & fees
Oct 22 - Oct 23
Baymont by Wyndham Easton
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.
A spacious dining area with multiple tables and chairs, large windows offering a view of the ocean, and a modern interior design.
A water park with multiple slides and pools, including a large green water slide and a lazy river.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
CA $91
CA $102 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Ocean City Oceanfront
A spacious lobby with a reception desk, seating area, and a television screen.
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.
A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
CA $155
CA $172 total
includes taxes & fees
Oct 26 - Oct 27
Comfort Inn & Suites Cambridge
A patio with outdoor seating, overlooking a marina with boats.
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.
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
CA $176
CA $195 total
includes taxes & fees
Nov 18 - Nov 19
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 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.

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
CA $118
CA $131 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Grasonville near Kent Island
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 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.

Hampton Inn Easton

Hampton Inn Easton
Easton
CA $180
CA $198 total
includes taxes & fees
Oct 29 - Oct 30
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.
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
CA $191
CA $210 total
includes taxes & fees
Oct 25 - Oct 26
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 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.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
CA $227
CA $298 total
includes taxes & fees
Nov 18 - Nov 19
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
CA $114
CA $128 total
includes taxes & fees
Nov 3 - Nov 4
DoubleTree by Hilton Ocean City Oceanfront
A hotel pool area with a water fountain, palm trees, and a multi-story building with balconies.
A balcony with a round table and chairs, overlooking the beach and ocean.
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
CA $162
CA $181 total
includes taxes & fees
Nov 1 - Nov 2
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 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
CA $302
CA $371 total
includes taxes & fees
Nov 15 - Nov 16
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 deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

The Oaks Waterfront

The Oaks Waterfront
Easton
CA $619
CA $681 total
includes taxes & fees
Nov 1 - Nov 2
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
"Great front office staff. Made me feel welcome from the get-go. Nice overall set-up with a restaurant on the premises and an outdoor bar with live music."
Robert 3-night trip
Posted 4 hours ago
Castle in the Sand
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 5 hours ago
The Americana Hotel
Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG

10/10 Excellent
"Room was clean, bed was comfortable. Hot tubs and pools were great! When indoor hot tubs wouldn't turn on, we approached the front desk. They called maintenance before we even turned away, and he arrived to fix them as we were walking back in! Took mere seconds, and he had the jets back up and running!"
Francine 2-night trip
Posted 11 hours ago
Holiday Inn Ocean City by IHG
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Staff was exceptional. Historical vibe was fun and coastal-appropriate. Close to DC and other fun destinations."
Kelly 4-night trip
Posted 1 day ago
St Michaels Inn
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 2 days ago
Grand Hotel Ocean City Oceanfront
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 2 days ago
Crystal Beach Hotel

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