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 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
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 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.
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.
$114 nightly
$127 total
Oct 18 - Oct 19
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
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.

2. 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
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.

3. 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
Sep 29 - Sep 30
Total with taxes and fees
Baymont by Wyndham Easton
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.

4. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$96 nightly
$105 total
Sep 23 - Sep 24
Total with taxes and fees
St Michaels Inn
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
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 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.
$135 nightly
$149 total
Sep 27 - Sep 28
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 balcony with a view of the ocean, featuring a railing and blue chairs.
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.

6. 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 hotel room with a desk, chair, blue sofa, ottoman, and a hallway leading to a door.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.
A spacious lobby with a reception desk, seating area, and a television screen.

7. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$116 nightly
$128 total
Sep 29 - Sep 30
Total with taxes and fees
Comfort Inn & Suites Cambridge
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.
A beach with a wooden boardwalk, umbrellas, and people.
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.

8. 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
A poolside area with blue lounge chairs and yellow umbrellas, a sign for Grand Hotel, and palm trees in the background.
A beachfront hotel with multiple balconies overlooking the ocean.
A hotel room with two beds, a balcony, a dining area, and a view of the city.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.

9. 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.
$94 nightly
$106 total
Oct 14 - Oct 15
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
An indoor swimming pool with clear water, tiled steps, and orange lounge chairs.
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 house with a glass door entrance, outdoor seating area with chairs, and a small table.
A hotel reception area with a herringbone patterned floor, reception desks, a flat-screen TV, and a view of the lobby.

10. Fenwick Inn

Fenwick Inn
North Ocean City
  • Dive into resort-style relaxation at this indoor pool oasis just steps from Maryland Beach.
$82 nightly
$92 total
Sep 23 - Sep 24
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 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 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
Sep 27 - Sep 28
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 pool area with multiple pools, lounge chairs, and a pool lift.
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.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
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.

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 modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.
A coffee station with two coffee machines and a variety of coffee pods and cups.

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
Easton
$149 nightly
$164 total
Oct 11 - Oct 12
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 blue sofa, a desk with a chair, a lamp, and a picture on the wall.
A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".
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
$116 nightly
$128 total
Sep 29 - Sep 30
Total with taxes and fees
Comfort Inn & Suites Cambridge
A modern indoor pool area with wooden beams, a pool, and seating arrangements.
A hotel room with two beds, a desk, a TV, a chair, and a large window with curtains.
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.

Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland
Fruitland
$122 nightly
$137 total
Sep 30 - Oct 1
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.
A hotel room with a bed, a sofa, a TV, a desk, 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 hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
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.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
$89 nightly
$98 total
Sep 29 - Sep 30
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 lobby with a reception desk, seating area, and a large wall mural.
A hotel with a prominent 'Best Western' sign, a brick facade, and a covered entrance.
A restaurant with a bar area, seating, and a kitchen in the background.

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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$266 nightly
$302 total
Oct 13 - Oct 14
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 marina with boats docked, a sandy beach, and a clear blue sky.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$266 nightly
$302 total
Oct 13 - Oct 14
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 large, multi-story hotel with a prominent Hilton sign, a parking lot with several cars, and a view of the ocean in the background.
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
$152 nightly
$170 total
Oct 18 - Oct 19
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 spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
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
$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 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
$489 nightly
$538 total
Sep 23 - Sep 24
Total with taxes and fees
The Oaks Waterfront
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
$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

Francis Scott Key Family Resort

Francis Scott Key Family Resort

8/10 Good
"I want to first highlight a gentleman by the name Donald; He was the nicest guy there., we arrived on Sunday. and the pools ware closed. now mind you it was after Labor Day weekend, but the main reason why I picked this place was because it showed on the website that the pool was still open outdoor and indoor. i went to the front desk the next day to ask why the pools weren't open the gentleman wasn't there. there were two ladies and the older one was extremely rude. I went back the next day to see if there was another person and I found Donald :) i mention to him the pool situation and he said I am so sorry about this yes, a lot of people that just got here have been having concerts about it. I will let the manager know. long story short he took care of it. we had a great time in the outdoor pool & indoor in the afternoon. it was a very nice place for my family, and I will definitely book my stay again next year. hoping that they will keep the pool open again. :)"
ALICIA 7-night trip
Posted 2 hours ago
Francis Scott Key Family Resort
Tidelands Caribbean Hotel and Suites

Tidelands Caribbean Hotel and Suites

10/10 Excellent
"Clean room,friendly personel,wonderful amenities!!!"
Deborah 2-night trip
Posted 3 hours ago
Tidelands Caribbean Hotel and Suites
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"Clean room great spot right on the boardwalk and Beach couldn't ask for more"
Marion 2-night trip
Posted 3 hours ago
Crystal Beach Hotel
Quality Inn Oceanfront

Quality Inn Oceanfront

10/10 Excellent
"The atrium area was very tropical in feel, including the tropical birds."
wayne 2-night trip
Posted 21 hours ago
Quality Inn Oceanfront
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 23 hours ago
Comfort Inn Gold Coast
Castle in the Sand

Castle in the Sand

10/10 Excellent
"Clean room"
Emil 1-night trip
Posted 1 day ago
Castle in the Sand

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