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 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
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 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.
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.
NT$3,495
NT$3,880 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.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
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.

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$4,294
NT$4,724 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.
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.
Marina

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,830
NT$5,361 total
includes taxes & fees
Oct 20 - Oct 21
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 pool area with multiple pools, lounge chairs, and a pool lift.
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.

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$4,099
NT$4,509 total
includes taxes & fees
Oct 7 - Oct 8
Best Western Plus Easton Inn & Suites
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 Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

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$4,063
NT$4,470 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.
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 spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows 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 beach view with a white fence, two green Adirondack chairs, and a white lounge chair.
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$2,404
NT$2,692 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 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.

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 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.
A hotel entrance with a clear sky, multiple flags, and a well-maintained lawn.

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, 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 swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
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.
NT$2,831
NT$3,114 total
includes taxes & fees
Oct 7 - Oct 8
Baymont by Wyndham Easton
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 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.
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
NT$3,495
NT$3,880 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 hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
NT$2,831
NT$3,114 total
includes taxes & fees
Oct 7 - Oct 8
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 pool area with multiple pools, lounge chairs, and a pool lift.
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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
NT$4,099
NT$4,509 total
includes taxes & fees
Oct 7 - Oct 8
Best Western Plus Easton Inn & Suites
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 outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
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
NT$4,294
NT$4,724 total
includes taxes & fees
Oct 18 - Oct 19
Fairfield Inn & Suites by Marriott 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 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.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
NT$6,069
NT$7,796 total
includes taxes & fees
Nov 4 - Nov 5
Hyatt Regency Chesapeake Bay
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A water park with multiple slides and pools, including a large green water slide and a lazy river.
A beach chair under a blue umbrella on a sandy beach with the ocean in the background.
A spacious dining area with multiple tables and chairs, large windows offering a view of the ocean, and a modern interior design.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
NT$2,319
NT$2,597 total
includes taxes & fees
Oct 18 - Oct 19
Hilton Garden Inn Ocean City Oceanfront
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 Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.
A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

Hampton Inn Easton

Hampton Inn Easton
Easton
NT$4,063
NT$4,470 total
includes taxes & fees
Oct 18 - Oct 19
Hampton Inn Easton
A spacious lobby with a reception desk, seating area, and a television screen.
A hotel room with a blue sofa, a desk with a chair, a lamp, and a picture on the wall.
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.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,552
NT$3,942 total
includes taxes & fees
Nov 5 - Nov 6
Comfort Inn & Suites Cambridge
A deck with two Adirondack chairs and a small table, overlooking a beach with the ocean and a clear sky.
A beach with a wooden boardwalk, umbrellas, and people.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.
A swimming pool with lounge chairs and umbrellas, surrounded by buildings and palm trees.

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
NT$2,542
NT$2,847 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Place Ocean City / Oceanfront
A resort with a swimming pool, sun loungers, and a view of the ocean.
A spa room with two hot tubs, a metal ladder, and a ceiling vent.
A fire pit in the center of a courtyard with lounge chairs and umbrellas in the background.
A dining area with a long table and six chairs, a grill, and potted plants.

Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG
North Ocean City
NT$2,097
NT$2,349 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Inn Ocean City by IHG
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 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.
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
NT$3,495
NT$3,880 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 hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
NT$2,831
NT$3,114 total
includes taxes & fees
Oct 7 - Oct 8
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 pool area with multiple pools, lounge chairs, and a pool lift.
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.

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
NT$4,099
NT$4,509 total
includes taxes & fees
Oct 7 - Oct 8
Best Western Plus Easton Inn & Suites
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 lobby with green sofas, a round table with a plant, and a lantern.

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
NT$2,105
NT$2,357 total
includes taxes & fees
Oct 29 - Oct 30
Grand Hotel Ocean City Oceanfront
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.
A kitchenette with a coffee machine, a framed picture, and a potted plant.
A restaurant with a counter, seating area, and a clock on the wall.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
NT$3,439
NT$3,817 total
includes taxes & fees
Oct 12 - Oct 13
Best Western Kent Narrows 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 outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
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
NT$4,294
NT$4,724 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 hotel room with a blue sofa, a desk with a chair, a lamp, and a picture on the wall.
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.

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,552
NT$3,942 total
includes taxes & fees
Nov 5 - Nov 6
Comfort Inn & Suites Cambridge
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
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.
Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,830
NT$5,361 total
includes taxes & fees
Oct 20 - Oct 21
Hyatt Place Kent Narrows & Marina
A resort with a swimming pool, sun loungers, and a view of the ocean.
A spa room with two hot tubs, a metal ladder, and a ceiling vent.
A fire pit in the center of a courtyard with lounge chairs and umbrellas in the background.
A dining area with a long table and six chairs, a grill, and potted plants.

Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG
North Ocean City
NT$2,097
NT$2,349 total
includes taxes & fees
Nov 3 - Nov 4
Holiday Inn Ocean City by IHG
A patio with outdoor seating, overlooking a marina with boats.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
An indoor swimming pool with clear views of boats and water.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
NT$4,403
NT$4,888 total
includes taxes & fees
Oct 20 - Oct 21
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.
View all properties

Top Eastern Shore Hotel Reviews

Tidelands Caribbean Hotel and Suites

Tidelands Caribbean Hotel and Suites

10/10 Excellent
"Rooms were very clean, staff was amazing.. Great experience, we will definitely book again."
Nickie 3-night trip
Posted 5 hours ago
Tidelands Caribbean Hotel and Suites
Castle in the Sand

Castle in the Sand

10/10 Excellent
"The bathroom was clean but a little in need of upgrades. The hotel staff were amazing so helpful and nice! Great location!"
Katherine 3-night trip
Posted 12 hours ago
Castle in the Sand
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

8/10 Good
"The room over"
Ken 2-night trip
Posted 16 hours ago
Carousel Resort Hotel & Condominiums
Comfort Suites Ocean City West

Comfort Suites Ocean City West

8/10 Good
"The room was clean. The rooms staff were friendly and helpful. Parking was satisfactory. Actually even had a spot for my trailer in the back during bike week. And then there was breakfast. Not so good there was one older black woman who was fantastic and did great with what they gave here to work with on Thursday morning. Highly recommend her. The rest of the staff on the other days was horrible. They could not keep the place clean or stocked. The Juice machine was falling apart and when they weren't out smoking they weren't helping. Do not recommend the breakfast unless they get their act together. Other than that we were satisfied with our stay at this location."
Donald 5-night trip
Posted 21 hours ago
Comfort Suites Ocean City West
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"Nice place. Great location"
Adrienne 2-night trip
Posted 2 days ago
Princess Bayside Beach Hotel
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 2 days ago
Plim Plaza Hotel
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 2 days ago
The Shore House
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 5 days ago
St Michaels Inn

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