Vacation rentals in Jamesport

The exterior of the cottage is highlighted by a well-maintained yard featuring a lush green lawn. A patio area with seating is visible, surrounded by flowering shrubs and trees. Multiple large windows offer a view into the inviting living spaces within.

4.95 out of 5 average rating, 76 reviews

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.

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A single-story house is depicted with a white exterior, featuring a light blue door and several windows. A pathway of stone slabs leads to the entrance, surrounded by neatly landscaped greenery and shrubs. Trees in the background show vibrant autumn foliage.

4.98 out of 5 average rating, 45 reviews

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!

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5.0 out of 5 average rating, 12 reviews

Apartment in Mattituck

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!

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4.98 out of 5 average rating, 184 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

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.

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4.87 out of 5 average rating, 30 reviews

A charming beach cottage is set against a clear blue sky, featuring a welcoming enclosed front porch. Surrounding gardens are filled with vibrant pink and purple flowers, framing the path leading to the front door and adding to the property’s tranquil ambiance.

Cottage in North Fork

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.

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A sunset casts golden hues over the water from a waterfront deck, showcasing the tranquil bay. Two images feature a sandy beach with gentle waves and a spacious patio adorned with green grass and seating for relaxation.

4.92 out of 5 average rating, 36 reviews

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! 🌊✨

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A modern living area is highlighted by a gray sofa centered on a low coffee table. Two armchairs are placed to one side, while a textured area rug complements the space. Wall art hangs above the sofa, and natural light enters through large windows.

4.96 out of 5 average rating, 167 reviews

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.

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A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

4.92 out of 5 average rating, 180 reviews

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.

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A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.

4.97 out of 5 average rating, 218 reviews

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.

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4.95 out of 5 average rating, 74 reviews

An outdoor deck features a dining table surrounded by six chairs, positioned over the water. The scene includes a marina with boats and lush greenery. A tranquil sunset casts soft hues across the landscape, enhancing the serene environment.

Cottage in Flanders

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.

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A spacious living area is highlighted by a large sectional sofa in light grey, positioned around a round coffee table. Abundant natural light floods in through sliding glass doors, with views of the outdoor space and a modern dining area visible in the background.

5.0 out of 5 average rating, 77 reviews

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.

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4.94 out of 5 average rating, 34 reviews

A spacious great room is highlighted by a cathedral ceiling with exposed wooden beams. Comfortable sofas frame a central coffee table, while large windows provide natural light, accentuated by sheer white curtains. A cozy reading nook is positioned against the wall, complemented by a variety of books.

Cottage in North Fork

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.

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Popular amenities for Jamesport vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Jamesport

4.96 out of 5 average rating, 23 reviews

The exterior of the house is visible, showcasing a charming facade with natural wood shingles. A well-maintained lawn surrounds the property. A driveway leads to a garage, while white chairs are positioned on the porch, inviting a relaxing outdoor experience.

Home in Southold

Country Beach Home!

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Superhost

An open living space features light-colored flooring and white walls. A dining table with four chairs is visible alongside a television mounted on a wall. Large glass doors lead to an outdoor area, enhancing the airy feel of the room.

4.83 out of 5 average rating, 23 reviews

NoFo Getaway: Pool, Farm Views, Beach Sunsets

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4.94 out of 5 average rating, 48 reviews

NOFO Ranch Home in Wine Cntry 2 Beaches 5 Min Walk

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4.9 out of 5 average rating, 10 reviews

Water Front Ospreys Nest Beach Rights Permit #1310

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A spacious backyard features a circular seating arrangement around a fire pit, with several black wooden chairs positioned on a bed of mulch. The backdrop includes a single-story home with a deck, surrounded by greenery and trees, under a blue sky with scattered clouds.

5.0 out of 5 average rating, 45 reviews

Mattituck Hideaway/ Luxury Wine Country Retreat

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A sandy path leads directly to a tranquil beach, framed by dunes and grasses. The calm waters of the Long Island Sound stretch to the horizon under a partly cloudy sky, creating a serene coastal scene.

4.96 out of 5 average rating, 56 reviews

Spacious Four Season Family Beach House

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A two-story house is set on a well-maintained lawn, featuring a paved driveway that leads to a garage. A pathway lined with shrubs directs attention to the inviting entrance with double doors, framed by decorative plants under a clear blue sky.

5.0 out of 5 average rating, 39 reviews

Peaceful Guesthouse

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