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 4 - Sep 5
Tomorrow
Sep 5 - Sep 6
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Eastern Shore hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
A modern food court with a central island, various food stations, and a yogurt display.
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.

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.
$119 nightly
$132 total
Oct 5 - Oct 6
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
Sep 27 - Sep 28
Total with taxes and fees
Best Western Plus Easton Inn & Suites
A multi-story hotel with a pool area, including sun loungers and a smaller pool.
A terrace with white plastic chairs and tables, blue umbrellas, and potted plants.
A beach with umbrellas and people.
An outdoor seating area with tables and chairs, overlooking a beach.

3. Park Place Hotel

Park Place Hotel
Downtown Ocean City
  • Relax at the oceanfront seasonal pool with loungers and umbrellas, just steps from the boardwalk for a perfect beach getaway.
$80 nightly
$88 total
Sep 29 - Sep 30
Total with taxes and fees
Park Place Hotel
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

4. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$87 nightly
$96 total
Sep 14 - Sep 15
Total with taxes and fees
St Michaels Inn
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.

5. 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 4 - Oct 5
Total with taxes and fees
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.
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.

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
Sep 13 - Sep 14
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
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 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".

7. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$115 nightly
$128 total
Sep 28 - Sep 29
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 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 lobby with green sofas, a round table with a plant, and a lantern.

8. 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.
$97 nightly
$109 total
Oct 5 - Oct 6
Total with taxes and fees
Grand Hotel Ocean City Oceanfront
A swimming pool with a metal ladder, lounge chairs, and a small building in the background.
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.
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.

9. Best Western Denton Inn

Best Western Denton Inn
Denton
  • Poolside retreat with a cozy fireplace lobby and complimentary breakfast makes this Denton stay refreshingly convenient.
$119 nightly
$132 total
Sep 7 - Sep 8
Total with taxes and fees
Best Western Denton Inn
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 modern lounge area with multiple seating arrangements, including sofas and chairs, a central wooden planter, and ambient lighting.
A hotel room with two beds, a large window with a city view, a flat-screen TV, and a desk with a lamp.

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
Sep 21 - Sep 22
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 hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.
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.
A Holiday Inn Express sign with a green and blue logo, surrounded by landscaped garden beds and trimmed hedges.

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
Easton
$159 nightly
$175 total
Sep 6 - Sep 7
Total with taxes and fees
Holiday Inn Express Easton by IHG
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
Sep 27 - Sep 28
Total with taxes and fees
Best Western Plus Easton Inn & Suites
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.
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
Sep 13 - Sep 14
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton
A modern indoor pool area with wooden beams, a pool, and seating arrangements.
A spacious lobby with a mix of seating options, including sofas and chairs, and a bar area with stools.
A Hampton Inn & Suites with a covered entrance, brick facade, and well-maintained landscaping.
A modern hotel room with a kitchenette, a large mirror, a flat-screen TV, and a sofa.

Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland
Fruitland
$122 nightly
$137 total
Sep 13 - Sep 14
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 bed, a sofa, a TV, a desk, and a large window.
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
$118 nightly
$132 total
Sep 7 - Sep 8
Total with taxes and fees
Best Western Plus Pocomoke City
A rooftop terrace with wicker furniture, a fire pit, and a view of a 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 4 - Oct 5
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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 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.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
$115 nightly
$128 total
Sep 28 - Sep 29
Total with taxes and fees
Comfort Inn & Suites Cambridge
A spacious lobby with a wooden reception desk, a sofa, a staircase, and a reception area.
A hotel room with a large bathtub, a red chair, a small round table, and a bed with white linens.
A hotel with a covered entrance, multiple windows, and a brick facade.
A modern hotel room with a wooden floor, a red armchair, a grey sofa, a desk with a chair, and a lamp.

Country Inn & Suites by Radisson, Salisbury, MD

Country Inn & Suites by Radisson, Salisbury, MD
Salisbury
$84 nightly
$94 total
Sep 13 - Sep 14
Total with taxes and fees
Country Inn & Suites by Radisson, Salisbury, MD
A hotel corridor with a large screen displaying a construction site, a curved wooden wall, and an exit sign.
A modern bistro with a wooden reception desk, a counter with a menu board, and red upholstered chairs.
An indoor swimming pool with clear lanes, a lifeguard chair, and a sun lounger by the poolside.
A modern office space with multiple workstations, ergonomic chairs, and a comfortable seating area with a sofa and armchairs.

Courtyard by Marriott Salisbury

Courtyard by Marriott Salisbury
Salisbury
$117 nightly
$131 total
Sep 14 - Sep 15
Total with taxes and fees
Courtyard by Marriott Salisbury
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 modern lounge area with multiple seating arrangements, including sofas and chairs, a central wooden planter, and ambient lighting.
A hotel room with two beds, a large window with a city view, a flat-screen TV, and a desk with a lamp.

Fenwick Inn

Fenwick Inn
North Ocean City
$84 nightly
$95 total
Sep 21 - Sep 22
Total with taxes and fees
Fenwick Inn
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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
$273 nightly
$310 total
Sep 29 - Sep 30
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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.
A dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.
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
$156 nightly
$175 total
Oct 6 - Oct 7
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 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
$440 nightly
$484 total
Sep 7 - Sep 8
Total with taxes and fees
The Oaks Waterfront
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 dining area with round tables, high ceilings with ductwork, and a stone fireplace.
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
$210 nightly
$233 total
Sep 9 - Sep 10
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
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
$106 nightly
$118 total
Oct 5 - Oct 6
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

10/10 Excellent
"Staff were friendly and professional. The check-in & check-out process was easy. Rooms and facilities were clean, well kept and maintained. The resort had numerous amenities suitable for all ages. We would absolutely stay there again!"
Cassandra 1-night trip
Posted 4 hours ago
Francis Scott Key Family Resort
Castle in the Sand

Castle in the Sand

8/10 Good
"We had a great time. Ocean view room was great! Bar and restaurant was very nice. Quick service and food very good. Breakfast buffet was very nice, lots of choices. Beds were comfortable, full size coffee pot was wonderful, so much better than those tiny 4 cup ones. Cupboards stocked well. Always had fresh towels. Beach was nice , not over crowded."
Kelly 4-night trip
Posted 6 hours ago
Castle in the Sand
Quality Inn Oceanfront

Quality Inn Oceanfront

10/10 Excellent
"It was really pretty the only thing I did not like was the bathroom in the room they don’t correct it really good but other than that it’s pretty nice"
Isis 1-night trip
Posted 6 hours ago
Quality Inn Oceanfront
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

10/10 Excellent
"Warm welcome. Friendly staff."
Necati 3-night trip
Posted 6 hours ago
Princess Bayside Beach Hotel
Bonita Beach Hotel

Bonita Beach Hotel

8/10 Good
"We were able to check-in 2 hours early, which was nice. The carpet in the room wasn't as clean as we hoped, but overall we had a nice stay."
Andre'a 1-night trip
Posted 1 day ago
Bonita Beach Hotel
Crystal Beach Hotel

Crystal Beach Hotel

8/10 Good
"You pay extra for more than 2 adults. Do not be honest on your people staying. The more people entered increases the rate and they do not increase the key cards or towels, linens, etc. non smoking rooms, balcony, etc — completely understand — have a smoking area with benches to sit and relax!!"
Bernice 3-night trip
Posted 2 days ago
Crystal Beach Hotel
Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"The hotel was great but the restaurants weren't. They shorted us 3 crabs and left the clams off the meal. When asked about it they said they were out of clams and they would put 3 more crabs in for us.if your paying 140 for a meal you would think they'd te1ll you they were out of stuff when your ordering. Went to get some breakfast sandwiches for us and the waiter said I had to order from the bar. I waited 10 minutes and was totally ignored. No customers but me. So I got some sandwiches elsewhere."
jennifer 5-night trip
Posted 2 days ago
Plim Plaza Hotel

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