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 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 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.

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$3,281
NT$3,642 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.
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.
A hotel with a covered entrance, multiple floors, and a parking lot.

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$4,305
NT$4,736 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott Easton
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.
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$4,842
NT$5,375 total
includes taxes & fees
Oct 13 - Oct 14
Hyatt Place Kent Narrows & Marina
A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.
A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.
A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.

4. The Tidewater Inn

The Tidewater Inn
Easton
  • Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
NT$5,702
NT$6,272 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A hotel hallway with carpeted floors, white doors, and overhead lighting.
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 swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

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$4,481 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 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.
A hotel pool area with multiple pools, lounge chairs, and a pool lift.

6. 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$4,109
NT$4,520 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Plus Easton Inn & Suites
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".

7. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,596
NT$3,991 total
includes taxes & fees
Oct 27 - Oct 28
Comfort Inn & Suites Cambridge
A swimming pool with a diving board, a brick wall, and a building in the background.
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 high ceilings, large windows, and modern chandeliers.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

8. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Kids will love this resort's waterslide, private beach, and pools—a paradise for adventure with kayaking and year-round swimming options.
NT$6,371
NT$8,751 total
includes taxes & fees
Oct 27 - Oct 28
Hyatt Regency Chesapeake Bay
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
Exterior
A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a concrete deck.
Exterior

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$3,234
NT$3,590 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Chestertown
A reception desk with a clock, framed pictures, and a sign for express checkout.
A hotel room with a bed, a desk, a chair, and a nightstand.
A poolside area with lounge chairs and a mural of a sunset over water.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

10. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
NT$3,456
NT$3,836 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Kent Narrows Inn
View all properties

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 reception desk with a modern design, a digital display, and a check-in counter.
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.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
NT$3,281
NT$3,642 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.
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.
A hotel with a covered entrance, multiple floors, and a parking lot.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
NT$4,305
NT$4,736 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott Easton
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.
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$4,842
NT$5,375 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 hotel hallway with carpeted floors, white doors, and overhead lighting.
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 swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

Hampton Inn Easton

Hampton Inn Easton
Easton
NT$4,074
NT$4,481 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 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.
A hotel pool area with multiple pools, lounge chairs, and a pool lift.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
NT$4,109
NT$4,520 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Plus Easton Inn & Suites
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 spacious dining area with high ceilings, large windows, and modern chandeliers.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
NT$6,371
NT$8,751 total
includes taxes & fees
Oct 27 - Oct 28
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$3,991 total
includes taxes & fees
Oct 27 - Oct 28
Comfort Inn & Suites Cambridge
Room
A reception desk with a clock, framed pictures, and a sign for express checkout.
An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.
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$3,456
NT$3,836 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Kent Narrows Inn
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
Exterior
A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a concrete deck.
Exterior

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
NT$3,234
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 modern kitchen with dark wood cabinets, a microwave, a coffee machine, and a breakfast bar with a glass display case.
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

Wingate by Wyndham Salisbury MD Airport North
Salisbury
NT$2,762
NT$3,221 total
includes taxes & fees
Oct 4 - Oct 5
Wingate by Wyndham Salisbury MD Airport North
View all properties

Family-friendly hotels with pools in Eastern Shore

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 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.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
NT$3,281
NT$3,642 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.
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.
A hotel with a covered entrance, multiple floors, and a parking lot.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
NT$4,305
NT$4,736 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott Easton
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.
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$4,842
NT$5,375 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 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.
A hotel room with a large bed, a chair, a desk, and a television.

Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
NT$16,916
NT$18,607 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 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.
A hotel pool area with multiple pools, lounge chairs, and a pool lift.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
NT$4,109
NT$4,520 total
includes taxes & fees
Oct 4 - Oct 5
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 deck with white lounge chairs and a pool, overlooking a beach.
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$2,545
NT$2,851 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn Ocean City Boardwalk
A modern hotel dining area with a long table, four chairs, and three pendant lights.
A hotel hallway with carpeted floors, white doors, and overhead lighting.
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 swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

Hampton Inn Easton

Hampton Inn Easton
Easton
NT$4,074
NT$4,481 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 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 high ceilings, large windows, and modern chandeliers.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
NT$6,371
NT$8,751 total
includes taxes & fees
Oct 27 - Oct 28
Hyatt Regency Chesapeake Bay
Room
A reception desk with a clock, framed pictures, and a sign for express checkout.
An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.
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$3,456
NT$3,836 total
includes taxes & fees
Oct 4 - Oct 5
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 bar area with a central island, multiple stools, and a variety of bottles and glasses.
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$2,547
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.
View all properties

Top Eastern Shore Hotel Reviews

Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

10/10 Excellent
"My sister in law and I spent Sept 21-26 2026 for a girls trip. We were pleased with our ocean front balcony room and appreciated having the restaurant, indoor pool and hot tub on premises. We were there during the Sept nor'easter so not having to leave the hotel to eat was very nice. All the staff were polite and friendly. We plan to come again hoping to be able to enjoy the beach next time."
Teresa 4-night trip
Posted 17 hours ago
Carousel Resort Hotel & Condominiums
Francis Scott Key Family Resort

Francis Scott Key Family Resort

8/10 Good
"Great place for families lots of amenities to keep them entertained"
Reyna 2-night trip
Posted 2 days ago
Francis Scott Key Family Resort
Bonita Beach Hotel

Bonita Beach Hotel

8/10 Good
"I had a few mechanical issues like one electrical outlet not working, no working room telephone and the shower handle coming off in your hand."
Denise 4-night trip
Posted 3 days ago
Bonita Beach Hotel

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