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 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
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 reception desk with a modern design, a digital display, and a check-in counter.
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 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.
NT$3,505
NT$3,890 total
includes taxes & fees
Oct 25 - Oct 26
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 with a covered entrance, multiple floors, and a parking lot.
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.

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.
Marina
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
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.

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 6 - Oct 7
Best Western Plus Easton Inn & Suites
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 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.

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 living room with a leather sofa, a coffee table, and a bookshelf filled with books.
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.

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 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 deck with white lounge chairs and a pool, overlooking a beach.
A beach view from a balcony with a clear sky.

7. Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk
Downtown Ocean City
NT$2,410
NT$2,700 total
includes taxes & fees
Nov 5 - Nov 6
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 restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.
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.

8. The Wildset

The Wildset
Downtown St. Michaels
NT$7,296
NT$8,822 total
includes taxes & fees
Nov 3 - Nov 4
The Wildset
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A hotel entrance with a clear sky, multiple flags, and a well-maintained lawn.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
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$3,195
NT$3,546 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Chestertown
A hotel room with a large bed, bedside tables, a chair, a desk, a window with curtains, and a wall-mounted air conditioner.
A wooden pavilion with picnic tables and benches, a grill, and a red bench.
A reception desk with a clock, framed pictures, and a sign for express checkout.
A bathroom with a toilet, a bathtub, and a shower area.

10. 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
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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 reception desk with a modern design, a digital display, and a check-in counter.
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 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
NT$3,505
NT$3,890 total
includes taxes & fees
Oct 25 - Oct 26
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 with a covered entrance, multiple floors, and a parking lot.
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.

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.
Marina
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
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 hotel hallway with carpeted floors, white doors, and overhead lighting.
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.

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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
NT$4,110
NT$4,521 total
includes taxes & fees
Oct 6 - Oct 7
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 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

Hyatt Regency Chesapeake Bay
Cambridge
NT$6,085
NT$8,427 total
includes taxes & fees
Nov 4 - Nov 5
Hyatt Regency Chesapeake Bay
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 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".

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,561
NT$3,953 total
includes taxes & fees
Nov 5 - Nov 6
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 wooden pavilion with picnic tables and benches, a grill, and a red bench.
A reception desk with a clock, framed pictures, and a sign for express checkout.
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 desk, two chairs, a flat-screen TV, and a painting on the wall.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
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$3,195
NT$3,546 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 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.

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
Nov 1 - Nov 2
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 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 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
NT$3,505
NT$3,890 total
includes taxes & fees
Oct 25 - Oct 26
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 with a covered entrance, multiple floors, and a parking lot.
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.

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.
Marina
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
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 living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A golf course with a water hazard and surrounding trees.

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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
NT$4,110
NT$4,521 total
includes taxes & fees
Oct 6 - Oct 7
Best Western Plus Easton Inn & Suites
A balcony with two green Adirondack chairs facing 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 deck with white lounge chairs and a pool, overlooking a beach.
A beach view from a balcony with a clear sky.

Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk
Downtown Ocean City
NT$2,410
NT$2,700 total
includes taxes & fees
Nov 5 - Nov 6
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 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.

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 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

Hyatt Regency Chesapeake Bay
Cambridge
NT$6,085
NT$8,427 total
includes taxes & fees
Nov 4 - Nov 5
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 wooden pavilion with picnic tables and benches, a grill, and a red bench.
A reception desk with a clock, framed pictures, and a sign for express checkout.
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 bar area with a central island, multiple stools, and a variety of bottles and glasses.

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

Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"Nice place. Great location"
Adrienne 2-night trip
Posted 4 hours ago
Princess Bayside Beach Hotel
Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"It was mind blowing to see how big the rooms were and how fast the elevators worked. Balconies were big with table and 4 chairs. It was like an ikea apartment seriously would definitely stay again. The only thing I didn't like was $10 a day for parking"
Amber 2-night trip
Posted 5 hours ago
Holiday Inn & Suites Ocean City by IHG
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

8/10 Good
"The room was spacious and clean but for the price, the amenities were just okay. The pool is weirdly situated inside a gate next to an arcade that I'm guessing no one uses. Not a lot of space to sit near the poolside bar."
Tiffany 2-night trip
Posted 7 hours ago
Princess Royale Oceanfront Resort
Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"Great stay, love that they have entertainment and everything you need right there and it was just steps from the country calling music festival."
Nina 3-night trip
Posted 7 hours ago
Plim Plaza Hotel
Tidelands Caribbean Hotel and Suites

Tidelands Caribbean Hotel and Suites

10/10 Excellent
"Room was clean and staff was great."
Dawn 3-night trip
Posted 13 hours ago
Tidelands Caribbean Hotel and Suites
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 13 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 13 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 17 hours ago
The Shore House
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 1 day ago
Quality Inn Oceanfront

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