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

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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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$3,352
NT$3,721 total
includes taxes & fees
Nov 8 - Nov 9
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.
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.

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$4,315
NT$4,746 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.
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.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,853
NT$5,387 total
includes taxes & fees
Oct 19 - Oct 20
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 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.

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$4,118
NT$4,530 total
includes taxes & fees
Oct 13 - Oct 14
Best Western Plus Easton Inn & Suites
A modern hotel dining area with a long table, four chairs, and three pendant lights.
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.
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.
NT$4,083
NT$4,491 total
includes taxes & fees
Oct 15 - Oct 16
Hampton Inn Easton
A spacious lobby with a reception desk, seating area, and a television screen.
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.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

6. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,537
NT$3,927 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Cambridge
A two-story house with a porch, a front door, and a small garden 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.
A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

7. The Wildset

The Wildset
Downtown St. Michaels
NT$7,311
NT$8,840 total
includes taxes & fees
Nov 3 - Nov 4
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 spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.
A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.

8. The Tidewater Inn

The Tidewater Inn
Easton
  • Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
NT$5,715
NT$6,286 total
includes taxes & fees
Nov 1 - Nov 2
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.

9. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
NT$6,513
NT$8,042 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Chesapeake Bay Beach Club
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

10. 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$3,119
NT$3,462 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Chestertown
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 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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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$3,352
NT$3,721 total
includes taxes & fees
Nov 8 - Nov 9
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.
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.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
NT$4,315
NT$4,746 total
includes taxes & fees
Oct 18 - Oct 19
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 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.
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$4,118
NT$4,530 total
includes taxes & fees
Oct 13 - Oct 14
Best Western Plus Easton Inn & Suites
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
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.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,853
NT$5,387 total
includes taxes & fees
Oct 19 - Oct 20
Hyatt Place Kent Narrows & Marina
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 multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
NT$5,874
NT$7,579 total
includes taxes & fees
Nov 8 - Nov 9
Hyatt Regency Chesapeake Bay
A modern hotel dining area with a long table, four chairs, and three pendant lights.
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.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

Hampton Inn Easton

Hampton Inn Easton
Easton
NT$4,083
NT$4,491 total
includes taxes & fees
Oct 15 - Oct 16
Hampton Inn Easton
A spacious lobby with a reception desk, seating area, and a television screen.
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.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,537
NT$3,927 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Cambridge
A two-story house with a porch, a front door, and a small garden 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 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 restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

The Wildset

The Wildset
Downtown St. Michaels
NT$7,311
NT$8,840 total
includes taxes & fees
Nov 3 - Nov 4
The Wildset
A multi-story hotel with balconies, located near a waterfront.
A dining area with a table set for two, potted plants, and a view through large windows.
A modern bar area with a circular counter, bar stools, and a seating area with a view of bicycles outside.
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
NT$2,656
NT$3,454 total
includes taxes & fees
Nov 1 - Nov 2
Cambria Hotel Ocean City - Bayfront
A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
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
NT$3,119
NT$3,462 total
includes taxes & fees
Nov 8 - Nov 9
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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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$3,352
NT$3,721 total
includes taxes & fees
Nov 8 - Nov 9
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.
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.

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
NT$4,315
NT$4,746 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.
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.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,853
NT$5,387 total
includes taxes & fees
Oct 19 - Oct 20
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 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$4,118
NT$4,530 total
includes taxes & fees
Oct 13 - Oct 14
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 multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
NT$5,874
NT$7,579 total
includes taxes & fees
Nov 8 - Nov 9
Hyatt Regency Chesapeake Bay
A modern hotel dining area with a long table, four chairs, and three pendant lights.
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.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

Hampton Inn Easton

Hampton Inn Easton
Easton
NT$4,083
NT$4,491 total
includes taxes & fees
Oct 15 - Oct 16
Hampton Inn Easton
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$2,144
NT$2,401 total
includes taxes & fees
Nov 10 - Nov 11
Comfort Inn Ocean City Boardwalk
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 lobby with green sofas, a round table with a plant, and a lantern.
A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
NT$2,056
NT$2,303 total
includes taxes & fees
Nov 1 - Nov 2
Grand Hotel Ocean City Oceanfront
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 beachfront hotel with multiple floors and balconies, a sandy beach in the foreground, and a clear sky.
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.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
NT$2,592
NT$2,903 total
includes taxes & fees
Nov 2 - Nov 3
DoubleTree by Hilton Ocean City Oceanfront
A multi-story hotel with balconies, located near a waterfront.
A dining area with a table set for two, potted plants, and a view through large windows.
A modern bar area with a circular counter, bar stools, and a seating area with a view of bicycles outside.
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
NT$2,656
NT$3,454 total
includes taxes & fees
Nov 1 - Nov 2
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

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Several family members stayed here for a wedding in the area. Our suites were very nice. The full size refrigerator and even the stove came in very handy. The living area, bathroom and bedroom were roomy and comfortable. Would definitely stay here again."
Allison 3-night trip
Posted 7 hours ago
Princess Royale Oceanfront Resort
Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"I checked out a day early because of storm coming. I put everything away and then I had to call down the next day to see if I'd left a pair of gray shorts in the room. They did find a pair of gray shorts in the room but also tried to say the room smelled very badly of smoke and I never smoked in that room. So I'd watch yourself because who knows if somebody went in there after I checked out one of the employees and then was smoking in that room and trying to blame me"
Ruby 3-night trip
Posted 9 hours ago
Plim Plaza Hotel
Quality Inn Oceanfront

Quality Inn Oceanfront

10/10 Excellent
"loved the courtyard with all the plants, the pool and hot tubs, the birds, the bar area. the bartenders were very friendly and informative"
yvonne 3-night trip
Posted 11 hours ago
Quality Inn Oceanfront
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 11 hours ago
Days Inn by Wyndham Ocean City Oceanfront
St Michaels Inn

St Michaels Inn

10/10 Excellent
"na"
Jeffrey 2-night trip
Posted 12 hours ago
St Michaels Inn
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"Beautiful view"
Ellen 3-night trip
Posted 17 hours ago
Princess Bayside Beach Hotel
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

10/10 Excellent
"Was a pleasant stay would stay again or recommend to others"
Les 1-night trip
Posted 18 hours ago
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

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