Holiday rentals in Riverhead

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Cozy Home Near Farms & Wineries

Enjoy this home in Baiting Hallow near many entertaining activities. This home will offer comfort to all, whether you are staying alone or spending time with family together. We look forward to hosting you and making sure your stay can be as enjoyable as possible. With this home, you will have a private entrance with free parking that could fit up to 4 cars. This home could sleep up to 5 guests, with 2 beds and 1 sofa bed. NOTE: You will have access to entire house but no access to garage.

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

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.

Private Apartment 15 Min from The Hamptons Beaches

Close the bedroom door. Sink into a queen-size bed. Sleep in. This is your Long Island getaway, and nobody’s rushing you. This comfortable one-bedroom apartment gives you something a hotel room can’t — real space to spread out and actually relax. A private bedroom for sleeping, a separate living room for hanging out, and your own entrance so you come and go on your schedule. Located just minutes from The Hamptons beaches, with free parking and fast WiFi for a comfortable and easy stay.

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!

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

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.

Pet Friendly Beach Cottage on the Northfork

Our cottage is located in a friendly beach community in Calverton, Long Island, only 90 minutes from Manhattan, where you can unwind and relax by heading to the private beach to soak up some sun, dip into the protected calm waters, or take a long walk along shore. Check out instructions: Turn off lights and TV Close windows and doors Leave used towels in the tub Put keys where you found them Safe travels and come back

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Rustic Log Cabin, Long Island Vineyards

Escape to this 1930s Long Island log cabin-cathedral ceilings in the bedroom and living room, gas fireplace glowing, vintage furniture with a fresh twist. Full kitchen, twin beds for kids, all near vineyards and that suburban-but-country feel. Tucked in the suburbs, this cabin feels worlds away-like hiding in plain sight. Perfect for a quiet getaway.