A marina with numerous boats docked at wooden piers under a clear sky.

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Check availability on Eastern Shore Family Hotels

Tonight
Oct 17 - Oct 18
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Oct 18 - Oct 19
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Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Eastern Shore family-friendly hotels

Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
A reception desk with a modern design, a digital display, and a check-in counter.

1. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
NT$3,208
NT$3,561 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
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.
Marina

2. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,925
NT$5,467 total
includes taxes & fees
Oct 25 - Oct 26
Hyatt Place Kent Narrows & Marina
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.
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.

3. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
  • Family fun escape at Fairfield Inn Easton with indoor saltwater pool, complimentary breakfast, and convenient location.
NT$4,379
NT$4,817 total
includes taxes & fees
Oct 25 - Oct 26
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 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 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.

4. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
  • Family-friendly getaway with indoor pool offers fun activities, free breakfast, and comfortable spaces for all ages.
NT$3,856
NT$4,241 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Plus Easton Inn & Suites
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 two beds, a desk, a chair, a TV, and a window with curtains.
A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

5. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,565
NT$3,957 total
includes taxes & fees
Oct 27 - Oct 28
Comfort Inn & Suites Cambridge
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
A hotel hallway with carpeted floors, white doors, and overhead lighting.

6. Hampton Inn Easton

Hampton Inn Easton
Easton
  • Family-friendly adventure awaits with a comfortable indoor pool, super comfy beds, and thoughtful staff ready to make memories.
NT$4,143
NT$4,558 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Easton
A two-story house with a porch, a front door, and a small garden area.
A bathroom with white tiled walls, a showerhead, and a door.
A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.
A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.

7. The Wildset

The Wildset
Downtown St. Michaels
NT$7,420
NT$8,972 total
includes taxes & fees
Nov 3 - Nov 4
The Wildset
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.
An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".
A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.

8. The Tidewater Inn

The Tidewater Inn
Easton
  • Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
NT$5,800
NT$6,380 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A modern bathroom with a white sink, mirror, and toilet. There is a hand dryer and a towel rack.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

9. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
  • Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.
NT$3,162
NT$3,509 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Chestertown
Two claw machines with colorful designs and instructions visible through the glass.
A poolside area with blue lounge chairs and yellow umbrellas, a sign for Grand Hotel, and palm trees in the background.
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.

10. Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
  • Kids splash in two pools while enjoying a beachfront playground and arcade at this Ocean City boardwalk retreat.
NT$2,087
NT$2,337 total
includes taxes & fees
Nov 9 - Nov 10
Grand Hotel Ocean City Oceanfront
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Choose what matters most at family-friendly hotels in Eastern Shore

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Family-friendly hotels with free breakfast in Eastern Shore

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.
A beach with a wooden boardwalk, umbrellas, and people.
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
NT$2,592
NT$2,904 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Place Ocean City / Oceanfront
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
NT$2,630
NT$2,946 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Ocean City Oceanfront
Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
A reception desk with a modern design, a digital display, and a check-in counter.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
NT$3,208
NT$3,561 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
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
NT$6,156
NT$7,913 total
includes taxes & fees
Nov 10 - Nov 11
Hyatt Regency Chesapeake Bay
A pool area with lounge chairs, a hot tub, and a view of the ocean.
A modern hotel lobby with a central seating area, a reception desk, and a patterned carpet.
An outdoor patio with brick flooring, wooden pergola, and tables with chairs.
A hotel room with a bed, a desk, a chair, a TV, and a view of the outside.

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Midtown Ocean City
NT$1,900
NT$2,128 total
includes taxes & fees
Oct 26 - Oct 27
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
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 spa room with two hot tubs, a metal ladder, and a ceiling vent.
A beachside resort with sun loungers, umbrellas, and a view of the ocean.

Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG
North Ocean City
NT$2,106
NT$2,359 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Ocean City by IHG
A two-story building with a covered entrance and an American flag.
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 restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

St Michaels Inn

St Michaels Inn
St. Michaels
NT$2,595
NT$2,855 total
includes taxes & fees
Nov 15 - Nov 16
St Michaels Inn
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.
A water park with multiple slides and pools, including a large green water slide and a lazy river.
A spacious dining area with multiple tables and chairs, large windows offering a view of the ocean, and a modern interior design.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
NT$2,099
NT$2,351 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Ocean City Oceanfront
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 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.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
NT$2,887
NT$3,176 total
includes taxes & fees
Oct 18 - Oct 19
Baymont by Wyndham Easton
A balcony with two green Adirondack chairs facing a beach.
A beach view from a balcony with a clear sky.
A restaurant with multiple round tables and chairs, a flat-screen TV mounted on the wall, and a window with an umbrella.
A deck with white lounge chairs and a pool, overlooking a beach.

Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk
Downtown Ocean City
NT$2,176
NT$2,437 total
includes taxes & fees
Nov 16 - Nov 17
Comfort Inn Ocean City Boardwalk
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Family-friendly hotels with pools in Eastern Shore

Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
A reception desk with a modern design, a digital display, and a check-in counter.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
NT$3,208
NT$3,561 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
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
NT$6,156
NT$7,913 total
includes taxes & fees
Nov 10 - Nov 11
Hyatt Regency Chesapeake Bay
A multi-story hotel with a pool area, balconies, and a 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.
A hotel room with a large bed, two chairs, a desk, and a view of the city through the window.

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
NT$2,087
NT$2,337 total
includes taxes & fees
Nov 9 - Nov 10
Grand Hotel Ocean City Oceanfront
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.
A beach with a wooden boardwalk, umbrellas, and people.
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
NT$2,592
NT$2,904 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Place Ocean City / Oceanfront
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
NT$2,630
NT$2,946 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Ocean City Oceanfront
An outdoor seating area with colorful umbrellas and wooden tables, overlooking a beach.
A hotel room with two beds, a desk, a chair, a window with curtains, and a view of the outside.
A bustling bar with stools and a counter, various beer brands displayed, and a neon sign in the background.
A spacious lobby with a reception desk, potted plants, and a tiled floor.

The Americana Hotel

The Americana Hotel
Downtown Ocean City
NT$1,692
NT$1,895 total
includes taxes & fees
Oct 25 - Oct 26
The Americana Hotel
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 spa room with two hot tubs, a metal ladder, and a ceiling vent.
A beachside resort with sun loungers, umbrellas, and a view of the ocean.

Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG
North Ocean City
NT$2,106
NT$2,359 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Ocean City by IHG
A multi-story hotel with balconies, a beachside location, and various shops and restaurants.
An outdoor seating area with tables and chairs, overlooking a beach.
A multi-story hotel with a pool area, including sun loungers and a smaller pool.
A beach with umbrellas and people.

Park Place Hotel

Park Place Hotel
Downtown Ocean City
NT$1,960
NT$2,931 total
includes taxes & fees
Nov 2 - Nov 3
Park Place Hotel
A hotel room with a bed, a chair, a nightstand, a lamp, and a painting on the wall.
Exterior
A restaurant with a counter, seating area, and a clock on the wall.
An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
NT$2,912
NT$3,233 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Kent Narrows Inn
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.
A water park with multiple slides and pools, including a large green water slide and a lazy river.
A spacious dining area with multiple tables and chairs, large windows offering a view of the ocean, and a modern interior design.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
NT$2,099
NT$2,351 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn 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

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

8/10 Good
"Great oceanfront location suites were clean & spacious whirlpool tub was a plus will definitely be staying there again"
Marilyn 3-night trip
Posted 9 hours ago
Holiday Inn & Suites Ocean City by IHG
Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"Nice place to stay. Clean but dated. Shower took a long time to warm up."
John D 3-night trip
Posted 15 hours ago
Plim Plaza Hotel
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

10/10 Excellent
"The staff was amazing !!!!"
Colleen 2-night trip
Posted 15 hours ago
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 17 hours ago
St Michaels Inn
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

8/10 Good
"The room that we stayed in could have used a little cleaning. There was dust and a build up on top of the vents. A visible mold was visible at the base of the vertical blinds by the door leading to the balcony."
Michael 3-night trip
Posted 18 hours ago
Carousel Resort Hotel & Condominiums

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