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 4 - Oct 5
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Oct 5 - Oct 6
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Oct 9 - Oct 11
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Oct 16 - Oct 18

Our top choices for Eastern Shore family-friendly hotels

Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
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$3,282
NT$3,643 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express Annapolis East-Kent Island by IHG
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.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

2. 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$4,306
NT$4,737 total
includes taxes & fees
Oct 11 - Oct 12
Fairfield Inn & Suites by Marriott Easton
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
An outdoor event area with round tables and a view of the water.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,843
NT$5,376 total
includes taxes & fees
Oct 13 - Oct 14
Hyatt Place Kent Narrows & Marina
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 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.

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$4,110
NT$4,521 total
includes taxes & fees
Oct 5 - Oct 6
Best Western Plus Easton Inn & Suites
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
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 hotel hallway with carpeted floors, white doors, and overhead lighting.

5. 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$4,074
NT$4,482 total
includes taxes & fees
Oct 18 - Oct 19
Hampton Inn Easton
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.
A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.
An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".

6. The Tidewater Inn

The Tidewater Inn
Easton
  • Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
NT$5,703
NT$6,273 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
A balcony with two green Adirondack chairs facing a beach.
A beach view from a balcony with a clear sky.
A hotel room with two beds, a desk, and a chair. There is a window with curtains, a lamp, and a nightstand with a phone.
A beach view with a white fence, two green Adirondack chairs, and a white lounge chair.

7. Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk
Downtown Ocean City
NT$2,519
NT$2,821 total
includes taxes & fees
Nov 4 - Nov 5
Comfort Inn Ocean City Boardwalk
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 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.
A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

8. The Wildset

The Wildset
Downtown St. Michaels
NT$7,296
NT$8,822 total
includes taxes & fees
Nov 2 - Nov 3
The Wildset
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A hotel room with a large bed, a flat-screen TV mounted on the wall, a desk with a microwave, and a chair.
A hotel entrance with a clear sky, multiple flags, and a well-maintained lawn.
A modern bathroom with a white sink, mirror, and toilet. There is a hand dryer and a towel rack.

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$3,235
NT$3,590 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Chestertown
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 dining area with round tables, high ceilings with ductwork, and a stone fireplace.

10. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
NT$6,093
NT$7,574 total
includes taxes & fees
Oct 19 - Oct 20
The Inn at Chesapeake Bay Beach Club
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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

Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
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$3,282
NT$3,643 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with a 5 FT depth marking, a clock on the wall, and a seating area with chairs.
A hotel with a covered entrance, multiple floors, and a parking lot.
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
NT$4,306
NT$4,737 total
includes taxes & fees
Oct 11 - Oct 12
Fairfield Inn & Suites by Marriott Easton
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
An outdoor event area with round tables and a view of the water.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,843
NT$5,376 total
includes taxes & fees
Oct 13 - Oct 14
Hyatt Place Kent Narrows & Marina
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
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 hotel hallway with carpeted floors, white doors, and overhead lighting.

Hampton Inn Easton

Hampton Inn Easton
Easton
NT$4,074
NT$4,482 total
includes taxes & fees
Oct 18 - Oct 19
Hampton Inn 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 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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
NT$4,110
NT$4,521 total
includes taxes & fees
Oct 5 - Oct 6
Best Western Plus Easton Inn & Suites
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$6,245
NT$8,608 total
includes taxes & fees
Oct 18 - Oct 19
Hyatt Regency Chesapeake Bay
A spacious lobby with a reception desk, seating area, and a television screen.
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 wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,596
NT$3,992 total
includes taxes & fees
Oct 27 - Oct 28
Comfort Inn & Suites Cambridge
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.
A restaurant with a counter, seating area, and a clock on the wall.
A poolside area with lounge chairs and a mural of a sunset over water.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
NT$3,667
NT$4,070 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Kent Narrows Inn
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A hotel room with a bed, a nightstand, a chair, and a desk with a lamp.
A hotel room with a desk, two chairs, a flat-screen TV, and a painting on the wall.
A hotel reception area with a reception desk, a seating area, and a hallway leading to other rooms.

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
NT$3,235
NT$3,590 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Chestertown
A modern lobby with a reception desk, a seating area with a sofa and a plant, and a staircase leading to an upper level.
A hotel room with two beds, a desk with a chair, a TV, and a window with curtains.
A modern kitchen with dark wood cabinets, a microwave, a coffee machine, and a breakfast bar with a glass display case.
A hotel room with a bed, a TV mounted on the wall, a desk with a lamp, a sofa, and a window with curtains.

Wingate by Wyndham Salisbury MD Airport North

Wingate by Wyndham Salisbury MD Airport North
Salisbury
NT$2,762
NT$3,221 total
includes taxes & fees
Oct 11 - Oct 12
Wingate by Wyndham Salisbury MD Airport North
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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 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.
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$3,282
NT$3,643 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with a 5 FT depth marking, a clock on the wall, and a seating area with chairs.
A hotel with a covered entrance, multiple floors, and a parking lot.
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
NT$4,306
NT$4,737 total
includes taxes & fees
Oct 11 - Oct 12
Fairfield Inn & Suites by Marriott Easton
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
An outdoor event area with round tables and a view of the water.
Marina
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,843
NT$5,376 total
includes taxes & fees
Oct 13 - Oct 14
Hyatt Place Kent Narrows & Marina
A room with a view of a wooden deck and a gazebo by the water.
A golf course with a water hazard and surrounding trees.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
NT$16,345
NT$17,979 total
includes taxes & fees
Oct 26 - Oct 27
Inn at Perry Cabin
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 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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
NT$4,110
NT$4,521 total
includes taxes & fees
Oct 5 - Oct 6
Best Western Plus Easton Inn & Suites
A balcony with two green Adirondack chairs facing a beach.
A beach view from a balcony with a clear sky.
A hotel room with two beds, a desk, and a chair. There is a window with curtains, a lamp, and a nightstand with a phone.
A restaurant with multiple round tables and chairs, a flat-screen TV mounted on the wall, and a window with an umbrella.

Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk
Downtown Ocean City
NT$2,519
NT$2,821 total
includes taxes & fees
Nov 4 - Nov 5
Comfort Inn Ocean City Boardwalk
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.
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 hotel hallway with carpeted floors, white doors, and overhead lighting.

Hampton Inn Easton

Hampton Inn Easton
Easton
NT$4,074
NT$4,482 total
includes taxes & fees
Oct 18 - Oct 19
Hampton Inn Easton
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$6,245
NT$8,608 total
includes taxes & fees
Oct 18 - Oct 19
Hyatt Regency Chesapeake Bay
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.
A restaurant with a counter, seating area, and a clock on the wall.
A poolside area with lounge chairs and a mural of a sunset over water.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
NT$3,667
NT$4,070 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Kent Narrows Inn
A restaurant with multiple tables and chairs, large windows offering a view of the sea, and a stone wall on one side.
A hotel room with a bed, a desk, a chair, a TV, and a view of the ocean through a sliding door.
A spacious living area with a fireplace, comfortable seating, and a large window overlooking the interior.
A beach with a wooden deck, benches, and bicycles.

Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront

Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront
Downtown Ocean City
NT$2,548
NT$2,917 total
includes taxes & fees
Nov 1 - Nov 2
Howard Johnson Plaza Hotel by Wyndham 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

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 2 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 2 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 6 hours ago
The Shore House
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"Front desk check in was easy. Good amenities - room has mini kitchen, fridge, coffee and plenty of space for 2 bed room. Balcony with ocean view and chairs for the balcony. Indoor pool and outdoor pool, food shops inside. Bike rack & plenty of parking. I ate at the restaurant and food was delish. Service was great in there as well. Hotel is dated looks like it’s from the 80s theme but solid bones. Front desk young male for evening check in. Opportunity when he asked have i visited before? I said no and he gave my key cards and that was it. I said can you tell highlights of the hotel since I’ve been never been? Then he told me info."
Nicole 4-night trip
Posted 6 hours ago
Grand Hotel Ocean City Oceanfront
Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"Charging $10 per night for parking is ridiculous. I'm already paying high prices to stay there"
Denise 3-night trip
Posted 20 hours ago
Holiday Inn & Suites Ocean City by IHG
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 21 hours ago
Quality Inn Oceanfront

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