Family-friendly holiday rentals in Wading River

Little, cozy place near beach for a couple.

It's quiet and cozy here. The yard is completely fenced with tall living shrubs, flowers, and trees. There's a gas grill, a fire pit, and a place to dine under an umbrella in the garden. I rent out a separate half of the house to guests: one bedroom, a small kitchen combined with a hallway. Peace and quiet reign here. You won't be disturbed. Sometimes I go into my half of the house, but very rarely. There are no other guests on the property, just you. I don't charge extra for pets. Parking free.

Spacious 1Bedroom Apartment By Wineries & Beaches

Relax and unwind in this private, spacious 1-bedroom apartment designed for comfort, convenience, and a peaceful stay. Whether you’re here for a weekend getaway, visiting the North Fork wineries, or need a quiet place to work remotely, this space has everything you need. Enjoy fully private apartment with its own entrance and yard - giving you uninterrupted freedom. Comfortable bedroom, cozy living area & full kitchen Relax in or after a day exploring nearby beaches, wineries, and attractions.

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”.Walking/driving directions to local beaches,15minute walk to our community beach,Wildwood StPk(.6mi away).Niks deli nearby.Minutes by car to wineries,breweries,farm stands,EastWind,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house.NoTV but Wifi is good so bring your device for entertainment.

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

North Country Cottage

Located near Long Island's beautiful beaches, vineyards, and wedding venues, this cozy cottage in the woods provides a quiet and comfortable place to stay while visiting! A spacious patio extends the living area, adding space to enjoy the outdoors in front of the fire pit or outdoor dining table. This property is located behind the owners' home and uses a shared driveway. While the owner is close by to address any issues during your stay, your space allows for total privacy.

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

Welcome to Jeanette and Jims Airbnb! We are avid travelers and look forward to hosting you on your trip to beautiful Long Island! Lovely, clean updated private room with private separate entrance and bathroom. Great location on a quiet wooded acre. 2 miles from Splish Splash. 3.6 miles from the Long Island Aquarium. 8.7 miles from Cupsogue Beach. 4.8 miles from Baiting Hollow Farm Vineyard. So much to do near by. Head easily to the north or south fork!

Modern Farmhouse Retreat North Fork Wine Country

Escape to this modern farmhouse retreat in North Fork Wine Country. Enjoy a luxurious stay with a fully stocked kitchen, cozy fireplace, Spacious bedrooms, and spa-inspired bathrooms. Relax in peaceful surroundings close to farms, beaches, pumpkin & apple picking, Tanger Outlets, Splish Splash Water Park, and top wineries. Outdoor dining, private fire pit, scenic views, and nearby hiking trails make it perfect for families, couples, or friends.

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities.

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

Muwu in Wading River

A beautiful cabin in the woods with private beach access (a short walk to the beach from the house). The cabin comes with luxurious amenities such as sauna, spacious dual shower bathroom, 12 inch memory foam king bed, radiant floor heating, and gorgeous 25 ft tall ceilings. Create your best memories here!