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
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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.
$103 nightly
$114 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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 a building with columns.
A kitchen with a stone wall, a microwave, and various food items on the counter.
A residential area with a large building, a swimming pool, and well-maintained lawns.

2. 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 1 - Oct 2
Total with taxes and fees
Baymont by Wyndham Easton
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
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.
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.

3. 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.
$129 nightly
$142 total
Sep 27 - Sep 28
Total with taxes and fees
Best Western Plus Easton Inn & Suites
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
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.

4. 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 4 - Oct 5
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A multi-level hotel with a central pool area, multiple balconies, and indoor seating areas.
A beachfront hotel with multiple floors, balconies, and a large glass facade.
A hotel room with a bed, two blue chairs, a table, and a view of the beach.
A balcony with a view of the ocean, featuring a railing and blue chairs.

5. Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort
North Ocean City
  • Luxurious indoor pool retreat with beachfront bliss makes this ocean getaway a splash.
$108 nightly
$119 total
Oct 18 - Oct 19
Total with taxes and fees
Princess Royale Oceanfront Resort
A swimming pool with a 5ft depth marker, white lounge chairs, and tables arranged around the pool area.
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 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.
$113 nightly
$126 total
Sep 27 - Sep 28
Total with taxes and fees
Comfort Inn & Suites Cambridge
A poolside area with blue lounge chairs and yellow umbrellas, a sign for Grand Hotel, and palm trees in the background.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.
A hotel room with two beds, a balcony, a dining area, and a view of the city.
A lobby with green sofas, a round table with a plant, and a lantern.

7. 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.
$79 nightly
$89 total
Oct 25 - Oct 26
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.
A lobby with a reception desk, a clock, and a wall-mounted deer head.
A bathroom with a shower, toilet, and a wheelchair-accessible chair.

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.
$127 nightly
$141 total
Oct 1 - Oct 2
Total with taxes and fees
Best Western Kent Narrows Inn
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.
A beach with a wooden boardwalk, umbrellas, and people.
A hotel room with a large bed, a desk, a chair, and a view of the city through large windows.
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.

9. Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
  • Oceanside pool escape in Maryland features refreshing indoor and seasonal outdoor pool with poolside loungers and bar service.
$110 nightly
$123 total
Oct 5 - Oct 6
Total with taxes and fees
Hyatt Place Ocean City / Oceanfront
An indoor swimming pool with clear water, tiled steps, and orange lounge chairs.
A modern house with a glass door entrance, outdoor seating area with chairs, and a small table.
A hotel room with two beds, a large window with a city view, a flat-screen TV, and a desk with a lamp.
A modern lounge area with multiple seating arrangements, including sofas and chairs, a central wooden planter, and ambient lighting.

10. Fenwick Inn

Fenwick Inn
North Ocean City
  • Dive into resort-style relaxation at this indoor pool oasis just steps from Maryland Beach.
$84 nightly
$95 total
Oct 12 - Oct 13
Total with taxes and fees
Fenwick 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

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.
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.
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 4 - Oct 5
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
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.
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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$129 nightly
$142 total
Sep 27 - Sep 28
Total with taxes and fees
Best Western Plus Easton Inn & Suites
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 modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
$152 nightly
$169 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.
A Holiday Inn Express sign with a green and blue logo, surrounded by landscaped garden beds and trimmed hedges.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A reception area with two reception desks, a wall-mounted sign reading "Holiday Inn Express," and a telephone on the right side.

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
Easton
$134 nightly
$147 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Easton by IHG
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 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
$113 nightly
$126 total
Sep 27 - Sep 28
Total with taxes and fees
Comfort Inn & Suites Cambridge
A modern indoor pool area with wooden beams, a pool, and seating arrangements.
A modern hotel room with a kitchenette, a large mirror, a flat-screen TV, and a sofa.
A spacious lobby with a mix of seating options, including sofas and chairs, and a bar area with stools.
A hotel room with two beds, a desk, a TV, a chair, and a large window with curtains.

Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland
Fruitland
$122 nightly
$137 total
Oct 4 - Oct 5
Total with taxes and fees
Hampton Inn & Suites Salisbury/Fruitland
A modern lobby with a reception desk, seating area, and artwork on the walls.
A hotel room with a large bed, bedside lamps, a nightstand, a window with blinds, and a wall-mounted abstract painting.
A modern restaurant with booths and tables, a kitchen area, and a large window.

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City
Pocomoke City
$127 nightly
$142 total
Sep 27 - Sep 28
Total with taxes and fees
Best Western Plus Pocomoke City
A kitchen with a stone wall, a microwave, and various food items on the counter.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.
A residential area with a large building, a swimming pool, and well-maintained lawns.
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
$89 nightly
$98 total
Oct 1 - Oct 2
Total with taxes and fees
Baymont by Wyndham Easton
A swimming pool with a metal ladder, lounge chairs, and a small building in the background.
A hotel with a prominent 'Best Western' sign, a brick facade, and a covered entrance.
A hotel lobby with a reception desk, seating area, and a large wall mural.
A hotel room with a bed, a sofa, a desk, and a chair. There are two lamps on the nightstands, a television, and a window with curtains.

Best Western Denton Inn

Best Western Denton Inn
Denton
$119 nightly
$132 total
Oct 4 - Oct 5
Total with taxes and fees
Best Western Denton 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 high ceilings, large windows, and modern chandeliers.
A marina with boats docked, a sandy beach, and a clear blue sky.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$245 nightly
$278 total
Oct 6 - Oct 7
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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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 high ceilings, large windows, and modern chandeliers.
A marina with boats docked, a sandy beach, and a clear blue sky.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$245 nightly
$278 total
Oct 6 - Oct 7
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.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
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
$135 nightly
$152 total
Oct 25 - Oct 26
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 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 spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
$214 nightly
$238 total
Oct 19 - Oct 20
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 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 wooden console table with framed floral artwork, two lamps, and two ottomans.

The Oaks Waterfront

The Oaks Waterfront
Easton
$489 nightly
$538 total
Sep 27 - Sep 28
Total with taxes and fees
The Oaks Waterfront
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 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 swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
$98 nightly
$109 total
Oct 12 - Oct 13
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
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

Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"I come stay here at least twice a year. Great staff great location great amenities for the area."
Herbert 3-night trip
Posted 2 hours ago
Crystal Beach Hotel
Fenwick Inn

Fenwick Inn

10/10 Excellent
"I did enjoy that the room was nice and cold when we checked other places you have to turn the air on. Other than that everything was amazing some staff members were a little bit off but you will always find 1-2 employees that you just don’t vibe well."
Jennifer 2-night trip
Posted 8 hours ago
Fenwick Inn
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"This was a great hotel. Staff couldn’t do enough for us. Room was clean. Bed was one of the best we have slept in on vacation. Sheets were soft and actually stayed on the bed. The kitchen area was efficient for a stay. Pool was clean. Restaurant was good. Highly recommended and we will be back."
Barbara 4-night trip
Posted 9 hours ago
Princess Royale Oceanfront Resort
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

8/10 Good
"Very clean, bedding, floors, bath Excellent beach view. Would stay here again"
John 2-night trip
Posted 12 hours ago
Days Inn by Wyndham Ocean City Oceanfront
Francis Scott Key Family Resort

Francis Scott Key Family Resort

10/10 Excellent
"Great place for kids to have fun and enjoy a vacation. It was close to everything and the food onsite was good. The room was beautifully clean and comfortable. Would definitely stay again. Thank you."
Rosemary 2-night trip
Posted 16 hours ago
Francis Scott Key Family Resort
Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"We only got one day of maid service in our room out of 8 days. Other than that...it was a decent value."
GUITAR STYLINGS 1-night trip
Posted 1 day ago
Plim Plaza Hotel
Comfort Inn Gold Coast

Comfort Inn Gold Coast

10/10 Excellent
"Hotel is very clean, room was very clean and comfortable. Great area."
Patrick 2-night trip
Posted 2 days ago
Comfort Inn Gold Coast

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