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 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
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.
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.
$110 nightly
$122 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
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.

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 6 - Oct 7
Total with taxes and fees
Baymont by Wyndham Easton
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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
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
Oct 6 - Oct 7
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 poolside area with lounge chairs and a mural of a sunset over water.
A hotel room with a large bed, bedside tables, a chair, a desk, a window with curtains, and a wall-mounted air conditioner.
A reception desk with a clock, framed pictures, and a sign for express checkout.

4. 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.
$115 nightly
$128 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Kent Narrows Inn
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 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.

5. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$112 nightly
$124 total
Nov 5 - Nov 6
Total with taxes and fees
Comfort Inn & Suites Cambridge
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.
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.

6. 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 11 - Oct 12
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
An outdoor event area with round tables and a view of the water.
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.

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 13 - Oct 14
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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 dining area with a long table and six chairs, a grill, and potted plants.
A beachside resort with sun loungers, umbrellas, and a view of the ocean.

8. 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.
$66 nightly
$74 total
Nov 3 - Nov 4
Total with taxes and fees
Holiday Inn Ocean City by IHG
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 patio with outdoor seating, overlooking a marina with boats.
A balcony with a view of a body of water, a row of buildings, and a chair.

9. 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 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 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.

10. 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.
$89 nightly
$100 total
Nov 1 - Nov 2
Total with taxes and fees
DoubleTree by Hilton 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 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
$110 nightly
$122 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, bedside tables, a chair, a desk, a window with curtains, and a wall-mounted air conditioner.
A wooden pavilion with picnic tables and benches, a grill, and a red bench.
A poolside area with lounge chairs and a mural of a sunset over water.
A restaurant with a counter, seating area, and a clock on the wall.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
$115 nightly
$128 total
Nov 1 - Nov 2
Total with taxes and fees
Best Western Kent Narrows Inn
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 lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135 nightly
$149 total
Oct 11 - Oct 12
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
Marina
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 13 - Oct 14
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 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
$233 nightly
$264 total
Nov 4 - Nov 5
Total with taxes and fees
Hyatt Regency Chesapeake Bay
A spacious lobby with a reception desk, seating area, and a television screen.
A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".
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
$112 nightly
$124 total
Nov 5 - Nov 6
Total with taxes and fees
Comfort Inn & Suites Cambridge
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A hotel hallway with carpeted floors, white doors, and overhead lighting.
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.

Hampton Inn Easton

Hampton Inn Easton
Easton
$128 nightly
$141 total
Oct 18 - Oct 19
Total with taxes and fees
Hampton Inn Easton
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
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.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
$89 nightly
$98 total
Oct 6 - Oct 7
Total with taxes and fees
Baymont by Wyndham Easton
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 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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$129 nightly
$142 total
Oct 6 - Oct 7
Total with taxes and fees
Best Western Plus Easton Inn & Suites
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.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
An indoor swimming pool with clear views of boats and water.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
$139 nightly
$154 total
Oct 19 - Oct 20
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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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
$233 nightly
$264 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 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.
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
$89 nightly
$100 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 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 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 dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
$111 nightly
$124 total
Nov 2 - Nov 3
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 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 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 6 - Oct 7
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

Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"Nice place. Great location"
Adrienne 2-night trip
Posted 8 hours ago
Princess Bayside Beach Hotel
Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"It was mind blowing to see how big the rooms were and how fast the elevators worked. Balconies were big with table and 4 chairs. It was like an ikea apartment seriously would definitely stay again. The only thing I didn't like was $10 a day for parking"
Amber 2-night trip
Posted 9 hours ago
Holiday Inn & Suites Ocean City by IHG
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

8/10 Good
"The room was spacious and clean but for the price, the amenities were just okay. The pool is weirdly situated inside a gate next to an arcade that I'm guessing no one uses. Not a lot of space to sit near the poolside bar."
Tiffany 2-night trip
Posted 11 hours ago
Princess Royale Oceanfront Resort
Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"Great stay, love that they have entertainment and everything you need right there and it was just steps from the country calling music festival."
Nina 3-night trip
Posted 11 hours ago
Plim Plaza Hotel
Tidelands Caribbean Hotel and Suites

Tidelands Caribbean Hotel and Suites

10/10 Excellent
"Room was clean and staff was great."
Dawn 3-night trip
Posted 17 hours ago
Tidelands Caribbean Hotel and Suites
Castle in the Sand

Castle in the Sand

8/10 Good
"The rooms were clean but lacked stuff to do dishes with and coffee"
Jessica 3-night trip
Posted 18 hours ago
Castle in the Sand
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

8/10 Good
"Rooms are decent. Beds are so uncomfortable though, we could barely sleep. My AC didn’t work either. Pool and hot tub area could use a good cleaning and upgrades. Hot tub doesn’t get up to appropriate temperature. Staff were very helpful though.coffee at the Bistro was excellent as well!"
Katie 3-night trip
Posted 18 hours ago
Carousel Resort Hotel & Condominiums
The Shore House

The Shore House

8/10 Good
"Quick one night stay before checking into our boardwalk hotel for the week. Clean small room with everything needed for one night. Easy check in and friendly staff. Would recommend for sure!"
Bree 1-night trip
Posted 21 hours ago
The Shore House
Quality Inn Oceanfront

Quality Inn Oceanfront

8/10 Good
"The room was clean and comfortable. The staff was friendly and helpful. The view was excellent. The property is somewhat dated and could use updated."
Carol 1-night trip
Posted 2 days ago
Quality Inn Oceanfront

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