Vacation rentals in Jamesport

Waterfront Beach Cottage

Renovated New Suffolk Waterfront Beach Cottage steps from water/beach/restaurants & more w/ water views from practically every window in the heart of the most special neighborhood in the north fork. Perfect for families with twn over full bunks, pvt mstr, grill, outdr shower and new kitchen. Bonus room has comfy couches & sunset views. Dine al fresco with water views or stroll to restaurants, apple picking or famous New Suffolk beach. Minutes from everything your vacation could need, year round.

Value · Location · Wifi

Brand New Charming Beach House

Brand New Construction in the heart of Mattituck. BEACH PASSES PROVIDED!! Charming 4 bed/2 bath beach house could be yours! Located in a quiet neighborhood. Home is in WALKING distance to the famous Love Lane & Strong’s Water Club. 2 minute drive in either direction to Peconic Bay Beaches or many LI sound beaches. Home has gourmet kitchen, fully decorated and furnished. Open ranch style. Large beautifully landscaped backyard & patio. Where the country meets the sea enjoy all NOFO has to offer!

Family · Location · Laundry

Mattituck 2BR: Open Layout, Deck, BBQ, Near Vines

Experience the North Fork lifestyle in this modern, open-concept 2-bedroom retreat. Perfectly situated in the heart of Mattituck, the airy layout seamlessly connects the kitchen, dining, and living areas for a spacious, social feel. Step out onto your private deck to grill on the BBQ after a day of exploring. You're minutes from the charm of Love Lane, the family fun at Harbes Farm, and premier tastings at Macari and Sparkling Pointe vineyards. Grab local treasures and come home to relax!

Family · Location · Cleanliness

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.

Value · Location · Grill

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.

Family · Location · Amenities

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! 🌊✨

Family · Location · Backyard

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.

Location · Value · Cleanliness

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.

Value · Location · Outdoor spaces

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.

Family · Location · Outdoor spaces

Bayside bliss - Charming 2bdrm on the water w dock

Lovely 2 bedroom cottage located on the water with your own private dock. 2 queen beds, 1 bathroom, and full kitchen. Enjoy a blissful kayak along the shores of the Peconic Bay. Easy access to the North and South Forks of Long Island, famous wine trails, Ocean Beaches, and amazing farms. 2 kayaks included in the rental. Experience the food, drink, and beautiful scenery with a short drive to all of the Hamptons and the North Fork.

Location · Family · Nearby

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.

Value · Family · Backyard

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.

Value · Location · View