Vacation rentals with outdoor seating in Cutchogue

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!

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.

Summer Retreat at the beach , enjoy Wine Country

* We provide a Beach Parking Pass for all Southold Town Beaches * 10 min walk to neighborhood sandy beach! * 5 min walk to vineyard with tasting room. Spacious Contemporary home. Master Bedroom plus 2 more bedrooms and 2 bathrooms on the second floor. Living room & kitchen on main floor. Wake up to beautiful garden view. Large kitchen and dining area for the whole family. Just minutes from Long Island's wineries and wedding venues. This home comes complete with everything you need!

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.

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Chic & Luxurious North Fork Farmhouse Retreat Set on a private 1-acre lot, this stylish farmhouse offers a pool, lounge areas, and refreshing ocean breezes. Just 1.5 hours from NYC, you’ll be minutes from beaches, wineries, farm stands, hiking, and golf. Inside, enjoy modern interiors, a full kitchen, and fast Wi-Fi. Perfect for families, couples, or friends, this retreat is ideal for a peaceful escape, remote work, or exploring wine country near the Hamptons and North Fork.

The Sandpiper

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact. Less than five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard, and Love Lane.

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).