Vacation rentals in Jamesport

4.95 out of 5 average rating, 22 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!

Perfection!! Amazing, centrally 🌊 located home in the middle of EVERYTHING that the North🍷Fork has to offer. BEAUTIFULLY designed with architectural details throughout. Open floor plan, large 🔥 fireplace. Huge Chefs 👩‍🍳 kitchen is AMAZING!! Minutes to Wine 🍷Country, farms, shoppes, and restaurants. So much to do or just relax 💤 and enjoy the beautiful tranquilpatio, new Weber BBQ, 🍗 and landscaped 🌹 yard. Beach gear, 10 beach chairs, 4 🍺 coolers, 4 beach 🏖️ umbrellas, beach toys/games for you

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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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A spacious living area is illuminated by natural light from skylights and large windows. A soft sofa is positioned on a light-colored rug, accompanied by a round pouf. Dining space is visible in the background, showcasing a simple wooden table and chairs.

4.95 out of 5 average rating, 87 reviews

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

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A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

4.93 out of 5 average rating, 136 reviews

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.

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A serene view of Laurel Lake is presented, featuring a spacious patio area with multiple Adirondack chairs arranged facing the water. The calm lake reflects the clear blue sky, surrounded by lush greenery and a wooden dock extending towards the water.

4.98 out of 5 average rating, 52 reviews

Lakehouse Getaway North Fork

Welcome to your perfect lakeside escape on the North Fork! This bright and airy 3-bedroom, 2-bath home sits on Laurel Lake with stunning views. This home features amenities designed for relaxation and recreation, including a cozy sunroom, hammock, outdoor shower, and canoe and kayaks for exploring the Lake. Guests can enjoy BBQs and gatherings on the porch. It’s ideal for unwinding or exploring local vineyards, farm stands, beaches, and more. This home offers the perfect North Fork getaway!

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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, 183 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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4.86 out of 5 average rating, 29 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 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, 166 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 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, 33 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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The exterior of a charming house is featured, showcasing warm orange siding with blue accents. A spacious deck with wooden railing and a grill is visible, surrounded by lush greenery. Large windows allow natural light into the interior, creating a welcoming atmosphere.

4.98 out of 5 average rating, 80 reviews

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.

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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

5.0 out of 5 average rating, 10 reviews

Serene and refined North Fork home with pool

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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

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A spacious driveway, lined with gravel and bordered by lush greenery, leads to a charming white cottage surrounded by well-manicured lawns. Tall trees provide shade, while an inviting garage is visible in the distance, contributing to the property's tranquil ambiance.

4.94 out of 5 average rating, 79 reviews

Walk to Love Lane! Immaculate Renovated Cottage.

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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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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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4.77 out of 5 average rating, 43 reviews

Apartment in Flanders

Stylish & Modern Touches Move-In-Ready

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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, 37 reviews

Peaceful Guesthouse

LocationFamilyShared spaces

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.