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 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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.
$110 nightly
$122 total
Oct 25 - Oct 26
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 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.

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
Oct 8 - Oct 9
Total with taxes and fees
Best Western Plus Easton Inn & Suites
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.
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

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.
$108 nightly
$120 total
Oct 14 - Oct 15
Total with taxes and fees
Best Western Kent Narrows Inn
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 hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.
A gym with a treadmill, elliptical, and stationary bike.

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 11 - Oct 12
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 a desk, chair, blue sofa, ottoman, and a hallway leading to a door.
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.

5. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$111 nightly
$124 total
Nov 1 - Nov 2
Total with taxes and fees
Comfort Inn & Suites Cambridge
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 balcony with a view of the ocean and beach.
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.

6. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
  • Plunge into ocean views at this beachfront hotel with 3 pools, where sun-drenched relaxation meets poolside cocktail service.
$81 nightly
$91 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.
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.

7. 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.
$80 nightly
$90 total
Nov 2 - Nov 3
Total with taxes and fees
Hyatt Place Ocean City / Oceanfront
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.
A balcony with a view of a body of water, a row of buildings, and a chair.
A balcony with a view of a marina and row houses.

8. 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.
$139 nightly
$154 total
Oct 19 - Oct 20
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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 beachfront hotel with multiple balconies overlooking the ocean.
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.
$64 nightly
$72 total
Nov 1 - Nov 2
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
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 hotel room with a large bed, a desk with a chair, a TV, and a balcony with a view of the sea.
A dining area with a long table and six chairs, a grill, and potted 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.
$69 nightly
$77 total
Nov 2 - Nov 3
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

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.
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.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135 nightly
$149 total
Oct 18 - Oct 19
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
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
$110 nightly
$122 total
Oct 25 - Oct 26
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.
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.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
$152 nightly
$169 total
Oct 18 - Oct 19
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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
$203 nightly
$231 total
Nov 4 - Nov 5
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
$129 nightly
$142 total
Oct 8 - Oct 9
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 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
Oct 18 - Oct 19
Total with taxes and fees
Hampton Inn Easton
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 a desk, chair, blue sofa, ottoman, and a hallway leading to a door.
A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
$111 nightly
$124 total
Nov 1 - Nov 2
Total with taxes and fees
Comfort Inn & Suites Cambridge
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
A balcony with a round table and chairs, overlooking the beach and ocean.
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.

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 hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A gym with a treadmill, elliptical, and stationary bike.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
$89 nightly
$98 total
Oct 11 - Oct 12
Total with taxes and fees
Baymont by Wyndham Easton
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 beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.
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
$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 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
$203 nightly
$231 total
Nov 4 - Nov 5
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 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 beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.
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
$81 nightly
$91 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
A balcony with a round table and chairs, overlooking the beach and ocean.
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.

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 hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
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
$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 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.
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 8 - Oct 9
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

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"This room was a diamond in the rough. I was pleasantly surprised with the entire establishment. I booked a room last minute (day of) and wasn't too hopeful. I just wanted to make sure I had a bed and a nice bathroom but I was in a time crunch. I booked it immediately and hoped for the best. When I arrived to the hotel, I was greeted by very helpful and nice staff who also gave me a little goody bag at check in. I was there for Country Calling music festival and they gave out clear bags with 2 emergency ponchos, koozies, 2 water bottles with electrolytes, ear plugs and the schedule! A small gift is such a huge gesture! The contents inside were incredible, very thankful for the bag. When I checked into my room, that's when I realized I had booked a suite. It was basically an apartment and when I checked in - I told all my friends about the great find and how I could basically live there, it was that cozy and clean. When you walk in, it was a sitting area/living room type area, then you walk through a hallway of a full kitchen with a big bathroom and then into your bed room that overlooks the boardwalk and ocean view. I was on the top floor, it was incredible. This hotel is on 17th street and the venue is at the end of the boardwalk - 1st. About a mile and a half walk but I enjoyed the room so much! I wish I had time to partake in the 1 of 3 pools I believe. The outdoor ones looked incredible but I believe there is also an outside one. One day, I must come back!"
Alexandra 2-night trip
Posted 14 hours ago
Holiday Inn & Suites Ocean City by IHG
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"The property was well maintained and the amenities were convenient and made the stay go very well."
sylvia 2-night trip
Posted 19 hours ago
Grand Hotel Ocean City Oceanfront
The Shore House

The Shore House

8/10 Good
"Good location"
Hugh 1-night trip
Posted 22 hours ago
The Shore House
Comfort Suites Ocean City West

Comfort Suites Ocean City West

10/10 Excellent
"Large room"
Lisa 3-night trip
Posted 23 hours ago
Comfort Suites Ocean City West
Castle in the Sand

Castle in the Sand

10/10 Excellent
"The bathroom was clean but a little in need of upgrades. The hotel staff were amazing so helpful and nice! Great location!"
Katherine 3-night trip
Posted 2 days ago
Castle in the Sand
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 6 days ago
St Michaels Inn

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