TOP Family-Friendly Hotels in Eastern Shore, MD for 2026 - Eastern Shore Family Welcoming Hotels

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

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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 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.

A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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.

£86

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

A kitchen with a stone wall, a microwave, and various food items on the counter.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.

A residential area with a large building, a swimming pool, and well-maintained lawns.

2. Baymont by Wyndham Easton

Easton

Family-oriented hotel delivers fun for all with seasonal outdoor pool and complimentary breakfast every morning.

£73

includes taxes & fees

1 Oct - 2 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 with a brick facade, multiple parking spaces, and a landscaped area with trees.

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

Easton

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

£106

includes taxes & fees

28 Sept - 29 Sept

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

An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

4. Fairfield Inn & Suites by Marriott Easton

Easton

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

£111

includes taxes & fees

4 Oct - 5 Oct

A spacious lobby with a reception desk, seating area, and a television screen.

A hotel room with a desk, chair, blue sofa, ottoman, and a hallway leading to a door.

A hotel room with a blue sofa, a desk with a chair, a lamp, and a picture on the wall.

A wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

5. Comfort Inn & Suites Cambridge

Cambridge

£94

includes taxes & fees

30 Sept - 1 Oct

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".

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.

6. The Tidewater Inn

Easton

Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.

£159

includes taxes & fees

30 Sept - 1 Oct

A modern hotel dining area with a long table, four chairs, and three pendant lights.

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.

A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

7. Hampton Inn Easton

Easton

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

£120

includes taxes & fees

25 Oct - 26 Oct

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.

8. Hyatt Place Kent Narrows & Marina

Grasonville

£126

includes taxes & fees

4 Oct - 5 Oct

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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

Best Western Plus Easton Inn & Suites

Easton

£106

includes taxes & fees

28 Sept - 29 Sept

Baymont by Wyndham Easton

Easton

£73

includes taxes & fees

1 Oct - 2 Oct

A lobby with seating, a reception desk, and a cityscape mural on the wall.

A hotel room with a bed, a sofa, a small table, a TV, and a framed picture on the wall.

A swimming pool with a blue interior, surrounded by lounge chairs and a changing area.

A spacious indoor area with multiple seating options including tables and booths, a bar area with a cityscape mural, and large windows providing natural light.

La Quinta Inn & Suites by Wyndham Newark - Elkton

Elkton

£84

includes taxes & fees

27 Sept - 28 Sept

Fairfield Inn & Suites by Marriott Easton

Easton

£111

includes taxes & fees

4 Oct - 5 Oct

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

Pocomoke City

£106

includes taxes & fees

27 Sept - 28 Sept

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A reception area with two reception desks, a wall-mounted sign reading "Holiday Inn Express," and a telephone on the right side.

Holiday Inn Express Easton by IHG

Easton

£111

includes taxes & fees

25 Oct - 26 Oct

A hotel room with two beds, a desk, a chair, and a wall-mounted TV.

A reception area with a modern design, featuring a reception desk, a mounted television, a clock, and a large painting on the wall.

A modern hotel with a prominent 'Wingate by Wyndham' sign, a covered entrance, and a flag.

An indoor swimming pool with clear glass walls, blue chairs around the pool, and a tiled floor.

Wingate by Wyndham North East

North East

£80

includes taxes & fees

4 Oct - 5 Oct

A multi-story hotel with a covered entrance, wheelchair-accessible parking, and a stone facade.

A modern hotel room with a wooden floor, a beige sofa, a small table, a bed, a wooden cabinet, a mirror, and a wall art piece.

A reception area with a blue accent wall, a wooden reception desk, and a flat-screen monitor.

A modern dining area with a long table and chairs, a kitchen area with a yellow backsplash, and a refrigerator.

Microtel Inn & Suites by Wyndham Salisbury

Salisbury

£77

includes taxes & fees

6 Oct - 7 Oct

Hyatt Place Kent Narrows & Marina

Grasonville

£126

includes taxes & fees

4 Oct - 5 Oct

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

A breakfast bar with a waffle maker, coffee machine, and juice dispenser.

A covered corridor with a series of doors, each marked with a number.

A hotel reception area with a check-in counter, a digital display, and a red carpet with the hotel's name.

Econo Lodge Easton Route 50

Easton

£67

includes taxes & fees

1 Oct - 2 Oct

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