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 18 - Oct 19
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Oct 19 - Oct 20
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Oct 23 - Oct 25
In two weeks
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 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.

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$3,208
NT$3,561 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
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.
Marina
An outdoor event area with round tables and a view of the water.

2. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,925
NT$5,467 total
includes taxes & fees
Oct 25 - Oct 26
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 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.

3. 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$4,379
NT$4,817 total
includes taxes & fees
Oct 25 - Oct 26
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 with a brick facade, multiple parking spaces, and a landscaped area with trees.
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.

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$3,856
NT$4,241 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Plus Easton Inn & Suites
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 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".

5. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,564
NT$3,956 total
includes taxes & fees
Oct 27 - Oct 28
Comfort Inn & Suites Cambridge
A modern lobby with a blue sofa, yellow armchairs, a white coffee table, and a patterned rug.
A modern hotel with a prominent "Hampton Inn" sign, a covered entrance, and a clean, welcoming facade.
A breakfast bar with a chalkboard wall displaying the word "EAT" and various food-related drawings. There are signs indicating dietary needs and caution for hot surfaces.
A hotel room with two beds, a desk, a chair, and a large window.

6. Hampton Inn Salisbury

Hampton Inn Salisbury
Salisbury
NT$3,396
NT$3,804 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Inn Salisbury
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.

7. The Tidewater Inn

The Tidewater Inn
Easton
  • Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
NT$5,800
NT$6,380 total
includes taxes & fees
Nov 1 - Nov 2
The Tidewater Inn
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.

8. The Wildset

The Wildset
Downtown St. Michaels
NT$7,420
NT$8,972 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 Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.
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$3,161
NT$3,509 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Chestertown
A swimming pool with a diving board, a brick wall, and a building in the background.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A marina with boats docked, a sandy beach, and a clear blue sky.

10. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Kids will love this resort's waterslide, private beach, and pools—a paradise for adventure with kayaking and year-round swimming options.
NT$5,022
NT$6,626 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
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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 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 beach with a wooden boardwalk, umbrellas, and people.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
NT$2,592
NT$2,903 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Place Ocean City / Oceanfront
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
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.
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.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
NT$2,630
NT$2,946 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Ocean City Oceanfront
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 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.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
NT$3,208
NT$3,561 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 multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A marina with boats docked, a sandy beach, and a clear blue sky.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
NT$5,022
NT$6,626 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A pool area with lounge chairs, a hot tub, and a view of the ocean.
A hotel with multiple balconies, a swimming pool, and a view of the ocean.
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
NT$1,900
NT$2,128 total
includes taxes & fees
Oct 26 - Oct 27
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
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$2,106
NT$2,359 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Ocean City by IHG
A two-story building with a covered entrance and an American flag.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A hotel room with two beds, a chair, and a painting on the wall.

St Michaels Inn

St Michaels Inn
St. Michaels
NT$2,595
NT$2,855 total
includes taxes & fees
Nov 1 - Nov 2
St Michaels Inn
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A spacious dining area with multiple tables and chairs, large windows offering a view of the ocean, and a modern interior design.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.
A water park with multiple slides and pools, including a large green water slide and a lazy river.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
NT$2,099
NT$2,351 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn Ocean City Oceanfront
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
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.
A gym with a treadmill, elliptical, and stationary bike.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
NT$2,887
NT$3,176 total
includes taxes & fees
Oct 19 - Oct 20
Baymont by Wyndham Easton
A balcony with two green Adirondack chairs facing a beach.
A restaurant with multiple round tables and chairs, a flat-screen TV mounted on the wall, and a window with an umbrella.
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$2,176
NT$2,437 total
includes taxes & fees
Nov 16 - Nov 17
Comfort Inn Ocean City Boardwalk
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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 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.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
NT$3,208
NT$3,561 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 multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A marina with boats docked, a sandy beach, and a clear blue sky.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
NT$5,022
NT$6,626 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A multi-story hotel with a pool area, balconies, and a view of the ocean.
A hotel room with a large bed, two chairs, a desk, and a view of the city through the window.
A lobby with green sofas, a round table with a plant, and a lantern.
A hotel room with two beds, a balcony, a dining area, and a view of the city.

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
NT$2,087
NT$2,337 total
includes taxes & fees
Nov 1 - Nov 2
Grand Hotel 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 beach with a wooden boardwalk, umbrellas, and people.
A modern hotel lobby with grey upholstered chairs, a round table, and a bar area.

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
NT$2,592
NT$2,903 total
includes taxes & fees
Nov 2 - Nov 3
Hyatt Place Ocean City / Oceanfront
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
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.
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.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
NT$2,630
NT$2,946 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Ocean City Oceanfront
An outdoor seating area with colorful umbrellas and wooden tables, overlooking a beach.
A spacious lobby with a reception desk, potted plants, and a tiled floor.
A balcony with a view of the ocean, a railing, and a beach in the background.
A bustling bar with stools and a counter, various beer brands displayed, and a neon sign in the background.

The Americana Hotel

The Americana Hotel
Downtown Ocean City
NT$2,537
NT$2,841 total
includes taxes & fees
Oct 25 - Oct 26
The Americana Hotel
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$2,106
NT$2,359 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Ocean City by IHG
A multi-story hotel with balconies, a beachside location, and various shops and restaurants.
A vibrant hotel lobby with a blue sofa, colorful artwork, a surfboard, and a modern chandelier.
A beach with umbrellas and people.
A multi-story hotel with a pool area, including sun loungers and a smaller pool.

Park Place Hotel

Park Place Hotel
Downtown Ocean City
NT$1,960
NT$2,931 total
includes taxes & fees
Oct 26 - Oct 27
Park Place Hotel
A hotel room with a bed, a chair, a nightstand, a lamp, and a painting on the wall.
An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.
A restaurant with a counter, seating area, and a clock on the wall.
A reception desk with a clock, framed pictures, and a sign for express checkout.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
NT$2,912
NT$3,233 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Kent Narrows Inn
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
A spacious dining area with multiple tables and chairs, large windows offering a view of the ocean, and a modern interior design.
A spacious living room with a view of the beach, featuring two sofas, a coffee table, and a bookshelf.
A water park with multiple slides and pools, including a large green water slide and a lazy river.

Hilton Garden Inn Ocean City Oceanfront

Hilton Garden Inn Ocean City Oceanfront
Midtown Ocean City
NT$2,099
NT$2,351 total
includes taxes & fees
Nov 8 - Nov 9
Hilton Garden Inn 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

Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"This is an older building by the ocean, so it may not be the fanciest place. But it is well-maintained and clean. The staff are very friendly, helpful, and, perhaps most importantly, everyone had a great attitude. It is a dog friendly hotel and it shows. They have a nice grassy area with a faux fire hydrant and bags to make it easy to clean up after your dog. I will stay here again."
Ginny 3-night trip
Posted 9 hours ago
Days Inn by Wyndham Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

8/10 Good
"Great place for a couples getaway or a whole family"
Ashley 1-night trip
Posted 11 hours ago
Princess Royale Oceanfront Resort
Castle in the Sand

Castle in the Sand

10/10 Excellent
"Nice location. Has an outdoor bar. Hair drier did not work but only stayed 1 night. Perhaps they would have corrected it.Iron worked fine. Furniture is outdated but ok of you don’t want luxury. Lo ed the bed and pillows."
Brian 1-night trip
Posted 14 hours ago
Castle in the Sand
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"Huge busy hotel, well maintained. Booked oceanfront room with jetted tub, and it was amazing. Located right on the boardwalk, super convenient. Parking is $10/night across the street."
Elena 2-night trip
Posted 18 hours ago
Grand Hotel Ocean City Oceanfront
Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"Nice place to stay. Clean but dated. Shower took a long time to warm up."
John D 3-night trip
Posted 2 days ago
Plim Plaza Hotel
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 2 days ago
St Michaels Inn

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