Family-friendly holiday rentals in Worcester County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Worcester County

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

The exterior of the home is showcased with a well-maintained lawn, framed by flowering shrubs. A welcoming front porch is visible, featuring two wooden benches. The entrance is highlighted by a maroon door, accompanied by classic shutters on the windows.

Home in Parsonsburg

4.99 out of 5 average rating, 174 reviews

Charming Home in a Neighborhood

Our home is well loved and is a great place to spend some quality family time. It is close to the Salisbury Airport (SBY), Salisbury University (SU), Perdue Stadium (Delmarva Shorebirds) and short drives to University of Maryland Eastern Shore (UMES), the beaches in Ocean City MD, Asseteauge Island, Md and some Delaware beaches too. Winterplace Equestrian Park is within 4 miles and Pemberton Historical Park is just across town. Price includes parking in the attached oversized 2 car garage.

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Guest favourite

A quaint white cottage with red door and windows is surrounded by lush greenery and blooming flowers. The entryway features a small path lined with shrubs, enhancing the inviting exterior. Sunlight casts gentle shadows on the well-maintained landscaping.

Tiny home in Snow Hill

4.89 out of 5 average rating, 329 reviews

Private cottage and gardens/comfortable queen bed.

Private cottage and gardens, comfortable Queen bed, full bath and kitchenette, within walking distance to historic Snow Hill. 30 min. drive to Ocean city and Assateague Island National park. This cottage was once a old school woodworking shop which is now on display at the old iron furnace town museum nearby. This beautiful three hundred year old town sits on the beautiful Pocomoke river with canoe, kayak, and bike rentals. Museums, art galleries, speciality shops, food and entertainment.

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Top Guest favourite

The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.

Townhouse in Ocean City

4.97 out of 5 average rating, 536 reviews

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

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Guest favourite

A spacious houseboat is docked securely along the water's edge, featuring large windows and a deck area. The surroundings include trees and a sandy space, creating a coastal atmosphere. The sky displays soft clouds illuminated by the setting sun.

Houseboat in Snow Hill

4.87 out of 5 average rating, 177 reviews

"Jolly"- Houseboat Getaway

"Tiny house on the water"! Jolly is a 42ft Holiday Mansion. Baywater Landing buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & deck areas to enjoy! 35 mins from Ocean City & Assateague Island. 45 mins from Chincoteague Island. Jolly remains docked, but guests have access to kayaks and paddle boards at no additional charge. Baywater Landing is secluded- some even say "boring"- but we think that's the whole point!

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Top Guest favourite

The backyard features a well-maintained putting green, with white flags marking the holes. A spacious home with a covered patio and landscaped garden is visible in the background, surrounded by lush greenery and trees.

Home in Berlin

4.98 out of 5 average rating, 104 reviews

Assateague, Golf, Ocean City, all Within Minutes!

Worcester Co. Lic. #859 PLEASE NOTE: number of allowed guests: No more than 8 golfers. (Min age 25) No more than 10 adults. (Min age 25) Related families up to 12 guests. We do NOT rent to high school senior groups. Please note, we own the white house next to our STR. Occasionally you may see us there, however, we are committed to your comfort & privacy. Located 1.5 miles from Assateague Island beaches. 3 courses within .5 miles. Towels and linens for every guest.

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Top Guest favourite

A spacious guest suite features a plush Queen bed with decorative pillows, a soft gray blanket, and a ceiling fan. Comfortable seating includes a yellow armchair and a light gray loveseat. A large TV is mounted on the wall, and a water cooler is positioned nearby.

Guest suite in Berlin

4.99 out of 5 average rating, 255 reviews

Berlin/Ocean City Suite- Relax/Refresh near beach!

A remodeled, above garage guest suite separate from the main house in America's Coolest Small Town, Berlin,Md! You will benefit from a separate entrance to your above garage suite which will allow you to enjoy your own quiet space to relax and embrace the small, quaint town of Berlin, all while a mere 15 minutes to the beaches of OCEAN CITY and Assateague! Multiple dining experiences and tons of shopping await you in either historic Berlin or world famous Ocean City!

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Top Guest favourite

A barn-style exterior of the condo is showcased, featuring a metal roof and three large garage doors at ground level. The second floor includes a deck with an entrance door. Expansive green space surrounds the property, with trees visible in the background under a clear blue sky.

Home in Berlin

4.96 out of 5 average rating, 118 reviews

SpaciousCondo nearOcean City|Winery|Golf on 5Acres

Come stay in our 2nd Floor Condo on our private 5-Acre Property! Enjoy the Barn-Like look from the outside, but inside, find a modern & spacious condo with a fully-equipped kitchen. Located in Berlin, Maryland, you are minutes to Historic Berlin and only 15 minutes to all the fun that Ocean City, Maryland has to offer! Have your morning coffee on the deck and soak in the scenic views or pitch a tent, light up the fire pit, let the kids run wild! We'll see you soon!

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Guest favourite

The open concept living area combines a kitchen, dining space, and lounging area, featuring light-toned cabinetry and modern appliances. A round dining table with two stools is positioned near a window, while a cozy couch and media console are arranged for comfort and convenience.

Apartment in Ocean City

4.92 out of 5 average rating, 136 reviews

Bright and Airy Oceanside Condo

Wake up to stunning ocean sunrises from your private balcony and enjoy bay sunsets just outside your front door. This oceanside condo in midtown Ocean City, MD is steps from the beach!! Beachside with no street to cross. Park your car for free in our covered lot. Enjoy a walkable location near top restaurants, bars, nightlife, and attractions like Seacrets, Fager’s Island, Macky’s, breakfast at barn 34 and mini golf. Ideal for a convenient Ocean City beach vacation.

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Top Guest favourite

A wooden dock extends over calm water, surrounded by tall trees. A pair of Adirondack chairs provide a peaceful spot to enjoy morning sunlight filtering through leaves, creating a serene atmosphere perfect for relaxation.

Home in Newark

5 out of 5 average rating, 124 reviews

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.

Indoor spacesFamilyCleanliness

Guest favourite

A two-story farmhouse features a welcoming porch and elegant landscaping, including trimmed bushes and a stone pathway. The exterior showcases a mix of wood and shingle siding, with large windows reflecting the greenery surrounding the property. A well-maintained lawn is visible in the foreground.

Home in Fruitland

4.97 out of 5 average rating, 134 reviews

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU

BEFORE BOOKING: Pool will be open 4/05/26 NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your reservation are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key

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Guest favourite

A cozy seating area features a light-colored couch adorned with decorative pillows. A woven coffee table rests on a natural fiber rug, while a window nook is lined with plants, allowing natural light to brighten the space. Wooden accents add a warm touch.

Tiny home in Salisbury

4.83 out of 5 average rating, 241 reviews

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

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Guest favourite

The exterior of a single-story cottage is visible, featuring light green siding and white shutters. A welcoming front porch is flanked by lush shrubs and greenery. A well-kept lawn and flower beds complement the home, set against a backdrop of trees.

Home in Berlin

4.98 out of 5 average rating, 113 reviews

3 Bed 2 Bath House in the Heart of Berlin

Walking distance to downtown Berlin! This cute, cozy, cottage offers a large master bedroom with a king size bed and bath, and two guest bedrooms with one queen size bed, one full size bed, and a bathroom across the hall. Located in America’s Coolest Small Town featuring many shops, restaurants, and bars with a close by brewery. Ocean City beaches and Assateague Island National Seashore are about 10-15 minutes away.

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