Vacation rentals in Jamesport

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.

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.

Charming Beach Cottage, Vineyards & Sunset Views

Take it easy at this unique and tranquil beach getaway. Steps to white sandy beach and walk to nearby steak & seafood restaurant as well as our local Post Office & Book Depisitory . Enjoy harvest season festivities, all in the heart of Long Island wine country! Exclusive & Historic South Jamesport is conveniently located on the Peconic Bay and scenic North Fork of Long Island. Explore vineyards, breweries, farm stands, restaurants combined with beautiful beaches.

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

5BR Beachfront Retreat | Water Views & Relaxation

Beachfront Bliss Awaits! 🏖️ Nestled on a private beach along the North Fork of Long Island, this newly updated retreat offers breathtaking Peconic Bay views and endless coastal adventures. Enjoy swimming, kayaking, clamming, fishing, or simply unwinding on the shore. With 5 spacious bedrooms, modern comforts, and just 5 minutes from top restaurants, wineries, and family fun, this is the perfect escape for relaxation and adventure. Book your stay today! 🌊✨

Walk to Beautiful Beach in Heart of Wine Country

Enjoy bright, comfortable and modern home in the heart of North Fork wine and farm country located just a quick walk from a gorgeous Peconic Bay beach with tennis/pickleball courts, volleyball and playground right on the beach. You'll have easy and quick access to the best of the east end: beautiful beaches, boating, fishing, fine and casual dining, vineyards, wineries, breweries, farms and farm stands offering fresh local produce, antique and local shops.

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.

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.

North Fork Farm House

This home is located on the North Fork of Long Island in the heart of wine country. We have a beautiful winery within close walking distance. We are surrounded by beautiful beaches and a short ferry ride to Shelter Island. There’s great restaurants and shopping just 15 minutes east in the town of Greenport or 5 minutes west to Love Lane in Mattituck. There is also lots to do in the town of Riverhead, including shopping at Tanger Outlets.

Immaculate NOFO Beach House Steps from Beach

Enjoy all the North Fork has to offer in this gorgeous, well stocked home. Nestled amongst 50+ vineyards/ breweries and the beautiful Peconic Bay (200 yards away!) the home is perfectly situated for your family to enjoy a relaxing vacation. Whether you are looking for a summer spent on the beach, a fall spent at harvest festivals or winter at the fire place vineyard tours, this is a great year round getaway.

Lovely North Fork Beach Cottage (2 BR/2 bath)!

Discover the North Fork of Long Island at the charming Beach Cottage (2BR/2BA). Nestled on 3 private acres, this idyllic wooded property boasts 100' of stunning *private* beachfront on the Great Peconic Bay! The Beach Cottage is spacious, tastefully-appointed, and fully-equipped to ensure a wonderful vacation. There are kayaks and SUPs for you to explore the bay and the sandy beach is a crowd pleaser.

Mattituck Dream House - Rental Opportunity

The Mattituck Dream House, is high on a hill overlooking the Mattituck Inlet on the North Side of town. Four bedrooms, with queen beds in 2 rooms, a full in one room and a king bed in the master suite. Friends tell me it feels like they are away at a destination vacation! I would like to rent my house for the summer, but I could also do monthly. June, July & August.