House holiday rentals in Jamesport

An open-concept living area features a modern kitchen with stainless steel appliances and a large island. Two checkered armchairs are positioned around a wooden coffee table, while a dining table awaits at the back, complemented by stylish chairs and natural light from the windows.

4.98 out of 5 average rating, 46 reviews

Beachside Paradise!!

Your search is over! Brand new construction 🔨. Charming Beautiful Beach 🏖 House ! Stunning 3 bedroom 1 and 1/2 bath with hot 🔥 water OUTDOOR shower. Walk 🏃‍♀️ down the block to the amazing and private Peconic Bay Beach. Home is beautifully designed with many architectural details including vaulted shiplap 🚢 ceilings & reclaimed wood 🪵 beams. Fully furnished and loaded up with all one needs for a great stay. Open floor plan, large kitchen and great room to 🥂 entertain. Separate 1 1/2 car garage!

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4.94 out of 5 average rating, 334 reviews

An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.

Home in Bridgehampton

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grounds are smoke-free.

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4.93 out of 5 average rating, 134 reviews

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.

Home in Mattituck

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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4.96 out of 5 average rating, 184 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

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4.94 out of 5 average rating, 116 reviews

A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.

Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

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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 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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A modern kitchen is showcased, featuring a large center island with four wooden bar stools. Stainless steel appliances and white cabinetry are complemented by granite countertops. Natural light filters in through a window above the sink, illuminating the inviting space.

4.95 out of 5 average rating, 152 reviews

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.

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Home in Westhampton Beach

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

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4.98 out of 5 average rating, 173 reviews

4.95 out of 5 average rating, 204 reviews

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.

Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

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5.0 out of 5 average rating, 77 reviews

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.

Home in Mattituck

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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