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 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 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$3,427
NT$3,804 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.
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$4,393
NT$4,833 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.
Marina

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
NT$4,863
NT$5,398 total
includes taxes & fees
Nov 18 - Nov 19
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 with a brick facade, multiple parking spaces, and a landscaped area with trees.
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.

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$3,884
NT$4,272 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 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.

5. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
NT$3,576
NT$3,969 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 hotel room with two beds, a desk, a chair, and a large window.
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.

6. Hampton Inn Salisbury

Hampton Inn Salisbury
Salisbury
NT$3,400
NT$3,808 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.
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".

7. The Tidewater Inn

The Tidewater Inn
Easton
  • Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
NT$5,819
NT$6,401 total
includes taxes & fees
Nov 2 - Nov 3
The Tidewater Inn
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel room with a bed, a sofa, a dining table, and a small round table.
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.
NT$3,191
NT$3,542 total
includes taxes & fees
Nov 15 - Nov 16
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 a view of the water, featuring a modern design with a marble floor and contemporary furniture.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

9. 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$4,765
NT$6,340 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
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
NT$6,979
NT$8,577 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 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$3,427
NT$3,804 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 covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.
A gym with a treadmill, elliptical, and stationary bike.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
NT$2,896
NT$3,186 total
includes taxes & fees
Oct 26 - Oct 27
Baymont by Wyndham Easton
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.
An outdoor patio with brick flooring, wooden pergola, and tables with chairs.
A hotel room with a bed, a desk, a chair, a TV, and a view of the outside.

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Midtown Ocean City
NT$1,907
NT$2,135 total
includes taxes & fees
Nov 9 - Nov 10
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Room
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.
A poolside area with lounge chairs and a mural of a sunset over water.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
NT$2,922
NT$3,243 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 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 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 swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
NT$2,638
NT$2,954 total
includes taxes & fees
Nov 3 - Nov 4
DoubleTree by Hilton Ocean City Oceanfront
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.
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
NT$2,723
NT$3,023 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Grasonville near Kent Island
A hotel room with a sofa, a TV, a bed, a window with a view of the sea, and a balcony.
A beach chair under a blue umbrella on a sandy beach with the ocean in the background.
A spacious living area with a large window overlooking a beach, furnished with sofas and a coffee table.
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
NT$2,106
NT$2,359 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
NT$2,601
NT$2,913 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 a view of the water, featuring a modern design with a marble floor and contemporary furniture.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
NT$4,765
NT$6,340 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 reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

St Michaels Inn

St Michaels Inn
St. Michaels
NT$2,604
NT$2,864 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 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$3,427
NT$3,804 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 a view of the water, featuring a modern design with a marble floor and contemporary furniture.
A marina with boats docked, a sandy beach, and a clear blue sky.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
NT$4,765
NT$6,340 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Regency Chesapeake Bay
Room
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.
A poolside area with lounge chairs and a mural of a sunset over water.

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
NT$2,922
NT$3,243 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 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.
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
NT$2,094
NT$2,345 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 hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.
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
NT$2,723
NT$3,023 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 covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.
A gym with a treadmill, elliptical, and stationary bike.

Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
NT$2,896
NT$3,186 total
includes taxes & fees
Oct 26 - Oct 27
Baymont by Wyndham Easton
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 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 swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
NT$2,638
NT$2,954 total
includes taxes & fees
Nov 3 - Nov 4
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 large hotel with multiple floors and balconies, situated on a beach with a clear sky.

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG
Downtown Ocean City
NT$2,937
NT$3,290 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 with multiple balconies, a swimming pool, and a view of the ocean.
An outdoor patio with brick flooring, wooden pergola, and tables with chairs.
A hotel room with a bed, a desk, a chair, a TV, and a view of the outside.

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Midtown Ocean City
NT$1,907
NT$2,135 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.
An indoor swimming pool with clear views of boats and water.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
NT$4,068
NT$4,515 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

Castle in the Sand

Castle in the Sand

10/10 Excellent
"Great front office staff. Made me feel welcome from the get-go. Nice overall set-up with a restaurant on the premises and an outdoor bar with live music."
Robert 3-night trip
Posted 8 hours ago
Castle in the Sand
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 15 hours ago
Holiday Inn Ocean City by IHG
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 2 days ago
Grand Hotel Ocean City Oceanfront
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"Great area to stay in plenty of great places to eat in walking distance and an excellent room with amazing room service"
Liam 3-night trip
Posted 2 days ago
Crystal Beach Hotel

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