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Nassau Point, North Fork Home w/ Pool

Whether you are looking for lots of outdoor space for the kids to explore, bike, play at the beach or splash around in the pool OR you are looking to explore all of the 38 Vineyards along Long Islands, this house is perfect for you. Open kitchen, dining and living space which then opens up to the deck and pool. 4 bedrooms, sleeping 8 comfortably. Two of the bedrooms are connected with a thru-door. Gated swimming pool. Minutes from the local sandy beach. Rental Permit: HMT24-00101 14-Day minimum

Kenney's Beach Loft - Vineyards, Horton Lighthouse

Kenny’s Beach Loft is a cozy, pet-friendly open-concept queen bed studio with 1 bathroom, a kitchenette, comfortable living and dining area, in-unit washer and dryer, and a private patio. Perfect for families and couples getaway. Just steps from Kenney’s Beach for stunning sunsets and peaceful walks. Minutes to Southold Fish Market, Croteaux Vineyards, Horton Point Lighthouse, and North Fork wineries for dining, wine tasting, and exploring. Enjoy coastal charm, seaside air, and total serenity.

Beautiful 1930s 4 bed 3 bath! Walk to Beach

Beautiful 1930s fully renovated cottage with 4 gorgeous bedrooms & 3 full baths. Spacious outdoor living space including an outdoor shower & fire pit. 1 block from a beautiful life guarded, sandy bay beach. Relax with the family at this peaceful place to stay in exclusive Fleets Neck and close to multiple spectacular wineries, breweries, farms, shopping outlets and worldclass restaurants. Stunning waterscapes abound! Enjoy a country retreat in a slice of heaven! Southold town permit 1137

Renovated 2-Bedroom Cottage on the North Fork

Serenity awaits as you step into this totally renovated Cottage. The property is perfectly located in the heart of Long Island's Wine Country. Centered on the North Fork this home allows you to explore all that there is to offer…. antique shops, restaurants, vineyards, breweries, farm stands and the beautiful Causeway Beach is just steps from this home. The home is newly renovated with a new kitchen, appliances, new bathroom, outdoor gas grill, fire pit and a beautiful screened in porch.

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 and provide a quiet and comfortable stay. About a 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.

Wine Country Home

Escape to the heart of Long Island’s Wine Country at our cozy, thoughtfully designed retreat. Surrounded by vineyards, farms, and picturesque countryside, our home offers the perfect blend of relaxation and adventure. Sip your way through nearby wineries, stroll local beaches, or enjoy North Fork shops and restaurants—all just minutes away. Whether you're here for a romantic getaway or weekend with friends/family, our home provides an ideal base for everything this lovely region offers.

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

Enjoy a relaxing getaway to the North Fork

One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

Sunny Harbor Suite

Escape to the tranquil beauty of the North Fork for a cozy romantic getaway, surrounded by lush vineyards, farm-to-table restaurants, quaint villages and blissful beaches. This completely private space includes two rooms: a large bedroom with a queen sized bed, a TV and a couch, as well as a private bathroom. The dining area includes a refrigerator, microwave and an electric tea kettle (I have organic coffee that you can make using a pour-over melita filter).

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

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.

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.