TOP Family Friendly Hotels in Eastern Shore for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels

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

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Check availability on Eastern Shore Family friendly Hotels

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Our top choices for Eastern Shore family-friendly hotels

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.

1. 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.

S$146

includes taxes & fees

1 Nov - 2 Nov

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 Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

A hotel hallway with carpeted floors, white doors, and overhead lighting.

2. Hampton Inn Easton

Easton

Family-friendly adventure awaits with a comfortable indoor pool, super comfy beds, and thoughtful staff ready to make memories.

S$180

includes taxes & fees

18 Oct - 19 Oct

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 lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

3. Fairfield Inn & Suites by Marriott Easton

Easton

Family fun escape at Fairfield Inn Easton with indoor saltwater pool, complimentary breakfast, and convenient location.

S$190

includes taxes & fees

18 Oct - 19 Oct

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

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.

4. Best Western Plus Easton Inn & Suites

Easton

Family-friendly getaway with indoor pool offers fun activities, free breakfast, and comfortable spaces for all ages.

S$181

includes taxes & fees

4 Oct - 5 Oct

A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.

A balcony with a view of the ocean and beach.

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 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.

5. DoubleTree by Hilton Ocean City Oceanfront

Midtown Ocean City

Family paradise at Ocean City beachfront with heated pools, playtime spaces, and seaside fun.

S$128

includes taxes & fees

1 Nov - 2 Nov

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

An outdoor event area with round tables and a view of the water.

6. Hyatt Place Kent Narrows & Marina

Grasonville

S$216

includes taxes & fees

13 Oct - 14 Oct

A balcony with white railings and orange chairs, overlooking a body of water and a distant shoreline.

A dining area with a table set for two, potted plants, and a view through large windows.

A modern bar area with a circular counter, bar stools, and a seating area with a view of bicycles outside.

A multi-story hotel with balconies, a prominent entrance, and a view of the water.

7. Cambria Hotel Ocean City - Bayfront

Downtown Ocean City

S$138

includes taxes & fees

26 Oct - 27 Oct

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.

8. Comfort Inn Ocean City Boardwalk

Downtown Ocean City

S$114

includes taxes & fees

1 Nov - 2 Nov

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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

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

S$146

includes taxes & fees

1 Nov - 2 Nov

Fairfield Inn & Suites by Marriott Easton

Easton

S$190

includes taxes & fees

18 Oct - 19 Oct

Hyatt Place Kent Narrows & Marina

Grasonville

S$216

includes taxes & fees

13 Oct - 14 Oct

Hampton Inn Easton

Easton

S$180

includes taxes & fees

18 Oct - 19 Oct

Best Western Plus Easton Inn & Suites

Easton

S$181

includes taxes & fees

4 Oct - 5 Oct

An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.

A spacious dining area with high ceilings, large windows, and modern chandeliers.

A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

Hyatt Regency Chesapeake Bay

Cambridge

S$351

includes taxes & fees

27 Oct - 28 Oct

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 hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

Comfort Inn & Suites Cambridge

Cambridge

S$160

includes taxes & fees

27 Oct - 28 Oct

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.

An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.

Best Western Kent Narrows Inn

Grasonville

S$154

includes taxes & fees

4 Oct - 5 Oct

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a concrete deck.

Comfort Inn & Suites Chestertown

Chestertown

S$144

includes taxes & fees

1 Nov - 2 Nov

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 a bed, a TV mounted on the wall, a desk with a lamp, a sofa, and a window with curtains.

A hotel with a swimming pool, lounge chairs, and a covered outdoor seating area.

A hotel room with two beds, a desk with a chair, a TV, and a window with curtains.

Wingate by Wyndham Salisbury MD Airport North

Salisbury

S$129

includes taxes & fees

4 Oct - 5 Oct

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Family-friendly hotels with pools in Eastern Shore

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

S$146

includes taxes & fees

1 Nov - 2 Nov