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
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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 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.

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.
AED 386
AED 428 total
includes taxes & fees
8 Nov - 9 Nov
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.
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.

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.
AED 496
AED 546 total
includes taxes & fees
18 Oct - 19 Oct
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 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.
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

Best Western Plus Easton Inn & Suites
Easton
  • Family-friendly getaway with indoor pool offers fun activities, free breakfast, and comfortable spaces for all ages.
AED 474
AED 521 total
includes taxes & fees
14 Oct - 15 Oct
Best Western Plus Easton Inn & Suites
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.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
Marina

4. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
AED 558
AED 620 total
includes taxes & fees
19 Oct - 20 Oct
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 Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

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.
AED 470
AED 517 total
includes taxes & fees
15 Oct - 16 Oct
Hampton Inn Easton
A two-story house with a porch, a front door, and a small garden area.
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 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 bathroom with white tiled walls, a showerhead, and a door.

6. The Wildset

The Wildset
Downtown St. Michaels
AED 841
AED 1,017 total
includes taxes & fees
3 Nov - 4 Nov
The Wildset
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 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.

7. The Tidewater Inn

The Tidewater Inn
Easton
  • Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
AED 611
AED 673 total
includes taxes & fees
1 Nov - 2 Nov
The Tidewater Inn
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

8. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
AED 749
AED 925 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Chesapeake Bay Beach Club
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 wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".
A hotel room with a blue sofa, a desk with a chair, a lamp, and a picture on the wall.

9. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
AED 407
AED 452 total
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Cambridge
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A gym with a treadmill, elliptical, and stationary bike.
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.

10. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
  • Family-oriented hotel delivers fun for all with seasonal outdoor pool and complimentary breakfast every morning.
AED 327
AED 360 total
includes taxes & fees
14 Oct - 15 Oct
Baymont by Wyndham Easton
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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 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.
A modern food court with a central island, various food stations, and a yogurt display.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
AED 386
AED 428 total
includes taxes & fees
8 Nov - 9 Nov
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.
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
AED 496
AED 546 total
includes taxes & fees
18 Oct - 19 Oct
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 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.
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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
AED 474
AED 521 total
includes taxes & fees
14 Oct - 15 Oct
Best Western Plus Easton Inn & Suites
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.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
AED 558
AED 620 total
includes taxes & fees
19 Oct - 20 Oct
Hyatt Place Kent Narrows & Marina
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 marina with boats docked, a sandy beach, and a clear blue sky.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
AED 676
AED 872 total
includes taxes & fees
8 Nov - 9 Nov
Hyatt Regency Chesapeake Bay
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 Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

Hampton Inn Easton

Hampton Inn Easton
Easton
AED 470
AED 517 total
includes taxes & fees
15 Oct - 16 Oct
Hampton Inn Easton
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 wooden building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".
A hotel room with a blue sofa, a desk with a chair, a lamp, and a picture on the wall.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
AED 407
AED 452 total
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Cambridge
A two-story house with a porch, a front door, and a small garden area.
A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.
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.

The Wildset

The Wildset
Downtown St. Michaels
AED 841
AED 1,017 total
includes taxes & fees
3 Nov - 4 Nov
The Wildset
A multi-story hotel with balconies, located near a waterfront.
A modern bar area with a circular counter, bar stools, and a seating area with a view of bicycles outside.
A balcony with white railings and orange chairs, overlooking a body of water and a distant shoreline.
A person sitting by a poolside with orange chairs and a drink.

Cambria Hotel Ocean City - Bayfront

Cambria Hotel Ocean City - Bayfront
Downtown Ocean City
AED 306
AED 397 total
includes taxes & fees
2 Nov - 3 Nov
Cambria Hotel Ocean City - Bayfront
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
AED 359
AED 398 total
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Chestertown
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 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.
A modern food court with a central island, various food stations, and a yogurt display.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
AED 386
AED 428 total
includes taxes & fees
8 Nov - 9 Nov
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.
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
AED 496
AED 546 total
includes taxes & fees
18 Oct - 19 Oct
Fairfield Inn & Suites by Marriott Easton
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.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
AED 558
AED 620 total
includes taxes & fees
19 Oct - 20 Oct
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 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.
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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
AED 474
AED 521 total
includes taxes & fees
14 Oct - 15 Oct
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 marina with boats docked, a sandy beach, and a clear blue sky.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
AED 676
AED 872 total
includes taxes & fees
8 Nov - 9 Nov
Hyatt Regency Chesapeake Bay
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 Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

Hampton Inn Easton

Hampton Inn Easton
Easton
AED 470
AED 517 total
includes taxes & fees
15 Oct - 16 Oct
Hampton Inn Easton
A balcony with two green Adirondack chairs facing a beach.
A deck with white lounge chairs and a pool, overlooking a beach.
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
AED 259
AED 290 total
includes taxes & fees
11 Nov - 12 Nov
Comfort Inn Ocean City Boardwalk
A multi-story hotel with a pool area, balconies, and a view of the ocean.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.
A hotel room with two beds, a balcony, a dining area, and a view of the city.
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
AED 237
AED 265 total
includes taxes & fees
1 Nov - 2 Nov
Grand Hotel Ocean City Oceanfront
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
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.
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.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
AED 298
AED 334 total
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Ocean City Oceanfront
A multi-story hotel with balconies, located near a waterfront.
A modern bar area with a circular counter, bar stools, and a seating area with a view of bicycles outside.
A balcony with white railings and orange chairs, overlooking a body of water and a distant shoreline.
A person sitting by a poolside with orange chairs and a drink.

Cambria Hotel Ocean City - Bayfront

Cambria Hotel Ocean City - Bayfront
Downtown Ocean City
AED 306
AED 397 total
includes taxes & fees
2 Nov - 3 Nov
Cambria Hotel Ocean City - Bayfront
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
"Clean room, friendly staff. Had atrium view."
Jill 2-night trip
Posted 3 hours ago
Carousel Resort Hotel & Condominiums
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"The location of the hotel was exceptional! It was within walking distance to multiple bars, restaurants, & stores. There is a boardwalk directly behind the hotel to walk along the beach. The view from our room was absolutely stunning! We're already thinking about making a return trip back! We had rain off & on but we didn't let that stop us from enjoying the balcony. We were on the top floor. We opted to pay $10 for a parking pass versus the first come street parking. There are spaces in a garage, or right in front of the hotel."
Amanda 1-night trip
Posted 4 hours ago
Grand Hotel Ocean City Oceanfront
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

10/10 Excellent
"had a great time beach view was amazing"
Florence 3-night trip
Posted 8 hours ago
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel
The Shore House

The Shore House

10/10 Excellent
"This place is the best bargain at the Beach!"
Bridget 1-night trip
Posted 11 hours ago
The Shore House
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

8/10 Good
"Great location and friendly staff"
Heather 2-night trip
Posted 1 day ago
Days Inn by Wyndham Ocean City Oceanfront
St Michaels Inn

St Michaels Inn

10/10 Excellent
"na"
Jeffrey 2-night trip
Posted 1 day ago
St Michaels Inn

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