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

Family friendly Hotels in Eastern Shore, Maryland

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Check availability on Eastern Shore Family friendly Hotels

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Eastern Shore family-friendly hotels

Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
A reception desk with a modern design, a digital display, and a check-in counter.

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.
P6,623
P7,352 total
includes taxes & fees
Nov 15 - Nov 16
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.
A hotel with a covered entrance, multiple floors, and a parking lot.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

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.
P8,525
P9,377 total
includes taxes & fees
Oct 25 - Oct 26
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.
An outdoor event area with round tables and a view of the water.

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
P9,588
P10,642 total
includes taxes & fees
Oct 26 - Oct 27
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 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.

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.
P7,506
P8,257 total
includes taxes & fees
Nov 15 - Nov 16
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 beach view from a balcony with a clear sky.
A beach view with a white fence, two green Adirondack chairs, and a white lounge chair.

5. Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk
Downtown Ocean City
P4,236
P4,744 total
includes taxes & fees
Nov 19 - Nov 20
Comfort Inn Ocean City Boardwalk
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 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.

6. 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.
P8,054
P8,859 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Easton
Two claw machines with colorful designs and instructions visible through the glass.
A poolside area with blue lounge chairs and yellow umbrellas, a sign for Grand Hotel, and palm trees in the background.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.
A lobby with green sofas, a round table with a plant, and a lantern.

7. Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
  • Kids splash in two pools while enjoying a beachfront playground and arcade at this Ocean City boardwalk retreat.
P4,056
P4,543 total
includes taxes & fees
Nov 1 - Nov 2
Grand Hotel Ocean City Oceanfront
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A hotel room with a bed, a sofa, a dining table, and a small round table.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.

8. 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.
P6,192
P6,873 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites Chestertown
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.
A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.
An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".

9. The Tidewater Inn

The Tidewater Inn
Easton
  • Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
P11,273
P12,401 total
includes taxes & fees
Nov 2 - Nov 3
The Tidewater Inn
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

10. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
P13,487
P16,576 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Chesapeake Bay Beach Club
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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 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.
A reception desk with a modern design, a digital display, and a check-in counter.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
P6,623
P7,352 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
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.
A gym with a treadmill, elliptical, and stationary bike.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
P5,612
P6,173 total
includes taxes & fees
Oct 21 - Oct 22
Baymont by Wyndham Easton
A pool area with lounge chairs, a hot tub, and a view of the ocean.
A hotel room with a bed, a desk, a chair, a TV, and a view of the outside.
A modern hotel lobby with a central seating area, a reception desk, and a patterned carpet.
An outdoor patio with brick flooring, wooden pergola, and tables with chairs.

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Midtown Ocean City
P3,694
P4,137 total
includes taxes & fees
Nov 9 - Nov 10
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Room
A lobby with a reception desk, a clock, and a wall-mounted deer head.
A gym with exercise equipment, a bench, and a wall-mounted mirror.
A kitchenette with a coffee machine, a framed picture, and a potted plant.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
P5,669
P6,293 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Kent Narrows Inn
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
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.
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
P5,109
P5,722 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Ocean City Oceanfront
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A spacious lobby with a staircase, a reception desk, and a dining area.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
P5,263
P5,842 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Grasonville near Kent Island
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A beach chair under a blue umbrella on a sandy beach with the ocean in the background.
A water park with multiple slides and pools, including a large green water slide and a lazy river.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
P4,080
P4,569 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Ocean City Oceanfront
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.
A beach with a wooden boardwalk, umbrellas, and people.

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
P5,038
P5,643 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Place Ocean City / Oceanfront
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 spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.
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
P10,155
P13,328 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A two-story building with a covered entrance and an American flag.
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A hotel room with two beds, a chair, and a painting on the wall.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

St Michaels Inn

St Michaels Inn
St. Michaels
P5,045
P5,549 total
includes taxes & fees
Nov 2 - Nov 3
St Michaels Inn
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Family-friendly hotels with pools in Eastern Shore

Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
A reception desk with a modern design, a digital display, and a check-in counter.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
P6,623
P7,352 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
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 spacious dining area with a view of the water, featuring a modern design with a marble floor and contemporary furniture.
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
P10,155
P13,328 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
Room
A lobby with a reception desk, a clock, and a wall-mounted deer head.
A gym with exercise equipment, a bench, and a wall-mounted mirror.
A kitchenette with a coffee machine, a framed picture, and a potted plant.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
P5,669
P6,293 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Kent Narrows Inn
A multi-story hotel with a pool area, balconies, and a view of the ocean.
A hotel room with two beds, a balcony, a dining area, and a view of the city.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.
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
P4,056
P4,543 total
includes taxes & fees
Nov 1 - Nov 2
Grand Hotel Ocean City Oceanfront
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A spacious lobby with a staircase, a reception desk, and a dining area.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
P5,263
P5,842 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Grasonville near Kent Island
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
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.
A gym with a treadmill, elliptical, and stationary bike.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
P5,612
P6,173 total
includes taxes & fees
Oct 21 - Oct 22
Baymont by Wyndham Easton
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
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.
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
P5,109
P5,722 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Ocean City Oceanfront
A clear pool with palm trees, lounge chairs, and umbrellas.
A beach with a row of multi-story hotels.
A balcony table with breakfast items and a view of the ocean.
A beachside bar with Adirondack chairs, a pool, and a view of the ocean.

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG
Downtown Ocean City
P5,677
P6,358 total
includes taxes & fees
Nov 18 - Nov 19
Holiday Inn & Suites Ocean City by IHG
A pool area with lounge chairs, a hot tub, and a view of the ocean.
A hotel room with a bed, a desk, a chair, a TV, and a view of the outside.
A modern hotel lobby with a central seating area, a reception desk, and a patterned carpet.
An outdoor patio with brick flooring, wooden pergola, and tables with chairs.

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Midtown Ocean City
P3,694
P4,137 total
includes taxes & fees
Nov 9 - Nov 10
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
A patio with outdoor seating, overlooking a marina with boats.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
An indoor swimming pool with clear views of boats and water.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
P7,862
P8,727 total
includes taxes & fees
Nov 18 - Nov 19
Hilton Garden Inn Kent Island Marina
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

Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"Though it is very clean, it is very dated. The views were amazing and it was close to everything we needed."
Lisa 2-night trip
Posted less than an hour ago
Plim Plaza Hotel
Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG

10/10 Excellent
"Room was clean, bed was comfortable. Hot tubs and pools were great! When indoor hot tubs wouldn't turn on, we approached the front desk. They called maintenance before we even turned away, and he arrived to fix them as we were walking back in! Took mere seconds, and he had the jets back up and running!"
Francine 2-night trip
Posted 1 hour ago
Holiday Inn Ocean City by IHG
Fenwick Inn

Fenwick Inn

10/10 Excellent
"It was great! Clean room. Staff was great!"
Jeanne 2-night trip
Posted 13 hours ago
Fenwick Inn
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Staff was exceptional. Historical vibe was fun and coastal-appropriate. Close to DC and other fun destinations."
Kelly 4-night trip
Posted 15 hours ago
St Michaels Inn
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

8/10 Good
"We found our room to be surprisingly spacious, very clean, and comfortable; however, the kitchenette/bathroom areas were a bit dated. The property location was excellent and there were restaurants and a pool within the property. The common areas inside the hotel and the outdoor space at the front of the hotel were adequate, but guests were somewhat disrespectful, leaving their trash, not replacing chairs after their use, etc... The staff was pleasant enough when checking-in and helpful when we had a question but were ignoring simple tasks like straightening up the common areas when time allowed. Although this was a little off-putting, we would return if the opportunity presented itself."
Keli 1-night trip
Posted 1 day ago
Grand Hotel Ocean City Oceanfront

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