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
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
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.
￥17,315
￥19,220 total
includes taxes & fees
Oct 25 - Oct 26
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 covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
A gym with a treadmill, elliptical, and stationary bike.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

2. 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.
￥14,023
￥15,425 total
includes taxes & fees
Oct 6 - Oct 7
Baymont by Wyndham 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 with a brick facade, multiple parking spaces, and a landscaped area with trees.

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.
￥20,301
￥22,331 total
includes taxes & fees
Oct 6 - Oct 7
Best Western Plus Easton Inn & Suites
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 bedroom with a large bed, a nightstand, a lamp, and a window with blinds.
An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".

4. The Tidewater Inn

The Tidewater Inn
Easton
  • Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
￥27,667
￥30,434 total
includes taxes & fees
Oct 27 - Oct 28
The Tidewater Inn
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.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

5. 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.
￥21,269
￥23,396 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott 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 two beds, a desk, a chair, a TV, and a window with curtains.
A hotel room with a blue sofa, a desk with a chair, a lamp, and a picture on the wall.

6. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
￥18,230
￥20,235 total
includes taxes & fees
Oct 27 - Oct 28
Comfort Inn & Suites Cambridge
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 hallway with carpeted floors, white doors, and overhead lighting.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

7. 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.
￥24,468
￥26,915 total
includes taxes & fees
Oct 15 - Oct 16
Hampton Inn 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.
An outdoor event area with round tables and a view of the water.
Marina

8. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
￥23,920
￥26,551 total
includes taxes & fees
Oct 6 - Oct 7
Hyatt Place Kent Narrows & Marina
A hotel lobby with a reception desk, seating area, and a large wall mural.
A hotel room with a bed, a sofa, a desk, and a chair. There are two lamps on the nightstands, a television, and a window with curtains.
A bathroom with a granite countertop sink, a toilet, and a mirror.
A restaurant with a bar area, seating, and a kitchen in the background.

9. Best Western Denton Inn

Best Western Denton Inn
Denton
  • Family-friendly pool oasis near Martinak State Park offers cool splashes and free perks for the whole gang.
￥18,688
￥20,743 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Denton Inn
A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A modern lounge area with seating, a fireplace, and a television.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel room with two beds, a desk, a TV, and a window with curtains.

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.
￥16,327
￥18,123 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Inn & Suites Chestertown
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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

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 with a brick facade, multiple parking spaces, and a landscaped area with trees.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
￥20,301
￥22,331 total
includes taxes & fees
Oct 6 - Oct 7
Best Western Plus Easton Inn & Suites
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
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.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
￥14,023
￥15,425 total
includes taxes & fees
Oct 6 - Oct 7
Baymont by Wyndham Easton
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
￥17,315
￥19,220 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Annapolis East-Kent Island by IHG
A lobby with seating, a reception desk, and a cityscape mural on the wall.
A hotel room with a bed, a sofa, a small table, a TV, and a framed picture on the wall.
A swimming pool with a blue interior, surrounded by lounge chairs and a changing area.
A hotel room with a desk, chair, sofa, and a TV. There are framed pictures on the wall and a window with curtains.

La Quinta Inn & Suites by Wyndham Newark - Elkton

La Quinta Inn & Suites by Wyndham Newark - Elkton
Elkton
￥16,264
￥18,214 total
includes taxes & fees
Oct 4 - Oct 5
La Quinta Inn & Suites by Wyndham Newark - Elkton
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.
An outdoor event area with round tables and a view of the water.
Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
￥23,920
￥26,551 total
includes taxes & fees
Oct 6 - Oct 7
Hyatt Place Kent Narrows & Marina
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.
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
￥21,269
￥23,396 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott Easton
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 hallway with carpeted floors, white doors, and overhead lighting.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

Hampton Inn Easton

Hampton Inn Easton
Easton
￥24,468
￥26,915 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 two beds, a desk, a chair, a TV, and a window with curtains.
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
￥18,230
￥20,235 total
includes taxes & fees
Oct 27 - Oct 28
Comfort Inn & Suites Cambridge
A multi-story hotel with a covered entrance, wheelchair-accessible parking, and a stone facade.
A modern dining area with a long table and chairs, a kitchen area with a yellow backsplash, and a refrigerator.
A reception area with a blue accent wall, a wooden reception desk, and a flat-screen monitor.
A modern hotel room with a wooden floor, a beige sofa, a small table, a bed, a wooden cabinet, a mirror, and a wall art piece.

Microtel Inn & Suites by Wyndham Salisbury

Microtel Inn & Suites by Wyndham Salisbury
Salisbury
￥14,793
￥16,568 total
includes taxes & fees
Oct 14 - Oct 15
Microtel Inn & Suites by Wyndham Salisbury
A swimming pool with a metal ladder, lounge chairs, and a small building in the background.
A hotel with a prominent 'Best Western' sign, a brick facade, and a covered entrance.
A restaurant with a bar area, seating, and a kitchen in the background.
A hotel room with a bed, a sofa, a desk, and a chair. There are two lamps on the nightstands, a television, and a window with curtains.

Best Western Denton Inn

Best Western Denton Inn
Denton
￥18,688
￥20,743 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Denton Inn
View all properties

Family-friendly hotels with pools in Eastern Shore

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 with a brick facade, multiple parking spaces, and a landscaped area with trees.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
￥20,301
￥22,331 total
includes taxes & fees
Oct 6 - Oct 7
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.
An outdoor event area with round tables and a view of the water.
Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
￥23,920
￥26,551 total
includes taxes & fees
Oct 6 - Oct 7
Hyatt Place Kent Narrows & Marina
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
￥17,315
￥19,220 total
includes taxes & fees
Oct 25 - Oct 26
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 covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
A gym with a treadmill, elliptical, and stationary bike.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
￥14,023
￥15,425 total
includes taxes & fees
Oct 6 - Oct 7
Baymont by Wyndham Easton
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.
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
￥21,269
￥23,396 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott 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 two beds, a desk, a chair, a TV, and a window with curtains.
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
￥18,230
￥20,235 total
includes taxes & fees
Oct 27 - Oct 28
Comfort Inn & Suites Cambridge
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 hallway with carpeted floors, white doors, and overhead lighting.
A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

Hampton Inn Easton

Hampton Inn Easton
Easton
￥24,468
￥26,915 total
includes taxes & fees
Oct 15 - Oct 16
Hampton Inn Easton
A swimming pool with a metal ladder, lounge chairs, and a small building in the background.
A hotel with a prominent 'Best Western' sign, a brick facade, and a covered entrance.
A restaurant with a bar area, seating, and a kitchen in the background.
A hotel room with a bed, a sofa, a desk, and a chair. There are two lamps on the nightstands, a television, and a window with curtains.

Best Western Denton Inn

Best Western Denton Inn
Denton
￥18,688
￥20,743 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Denton Inn
A modern lobby with a reception desk, seating area, and artwork on the walls.
A hotel room with a bed, a sofa, a TV, a desk, and a large window.
A hotel room with a large bed, bedside lamps, a nightstand, a window with blinds, and a wall-mounted abstract painting.
A modern restaurant with booths and tables, a kitchen area, and a large window.

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City
Pocomoke City
￥19,942
￥22,334 total
includes taxes & fees
Oct 13 - Oct 14
Best Western Plus Pocomoke City
A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A modern lounge area with seating, a fireplace, and a television.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel room with two beds, a desk, a TV, and a window with curtains.

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
￥16,327
￥18,123 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Inn & Suites Chestertown
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

Castle in the Sand

Castle in the Sand

8/10 Good
"Front desk was awesome. Room needs a little upkeep. Great view of the beach and Coconuts was a great little spot for live music"
Chad 3-night trip
Posted 3 hours ago
Castle in the Sand
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 4 hours ago
Francis Scott Key Family Resort
Fenwick Inn

Fenwick Inn

8/10 Good
"Our room/suite was fantastic! We stayed in room 521. My only complaints are the breakfast provided wasn’t great and the pool/hot tub area is in need of some improvement. But the hotel and staff itself were great! We would still stay there again."
Erin 4-night trip
Posted 10 hours ago
Fenwick Inn
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 1 day ago
Bonita Beach Hotel
Comfort Suites Ocean City West

Comfort Suites Ocean City West

8/10 Good
"The front desk staff was extremely helpful and courteous. The hotel, including the rooms were very clean. My only complaint being that when I returned from swimming in the pool one afternoon, that my room door was propped open by the housekeeping staff, with none of them in sight. I stood by for several minutes to see if anyone would return or was keeping an eye on the room, but nobody did. This was a little disconcerting as I had left valuable camera equipment along with my wallet, in the room while swimming. Nothing was missing but these actions left the room unsecure and anyone in the hotel could have easily gained access to it!"
Michael 3-night trip
Posted 2 days ago
Comfort Suites Ocean City West

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