House vacation 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, 44 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!

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.

4.94 out of 5 average rating, 72 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.

A large pool is surrounded by a well-maintained lawn, featuring shallow lounging areas and sleek white loungers. A shaded gazebo can be seen in the background, offering a space for relaxation, while trees and greenery add to the tranquil outdoor setting.

4.93 out of 5 average rating, 45 reviews

North Fork Extended-Stay Retreat, Pool, Beaches

Escape to the heart of Long Island's North Fork and enjoy a private farmhouse designed for extended stays. Whether you're working remotely, exploring wine country, spending time with family, or escaping the city for a few weeks, this peaceful retreat offers everything you need to settle in and relax. Surrounded by vineyards and farms, yet minutes from beaches, marinas, Love Lane, and Greenport Village, you'll experience the best of North Fork living from one central location. Rental permit 0925

4.85 out of 5 average rating, 151 reviews

Home in Hampton Bays

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

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.

5 out of 5 average rating, 37 reviews

Wine Country Home

Escape to the heart of Long Island’s Wine Country at our cozy, thoughtfully designed retreat. Surrounded by vineyards, farms, and picturesque countryside, our home offers the perfect blend of relaxation and adventure. Sip your way through nearby wineries, stroll local beaches, or enjoy North Fork shops and restaurants—all just minutes away. Whether you're here for a romantic getaway or weekend with friends/family, our home provides an ideal base for everything this lovely region offers.

4.94 out of 5 average rating, 54 reviews

A spacious gourmet kitchen is equipped with white cabinetry and a large island featuring a light-colored countertop. Pendant lights hang above the island, and stainless steel appliances are visible in the background, complemented by a tile backsplash and modern fixtures throughout.

Home in Southold

Luxury by the Sea!!

Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. This home is beautifully designed with too many architectural details to list. Property is fully furnished 🛋 with no detail spared . Open floor plan, spacious great room with gas fire place and flat screen, gourmet eat 🍝 in kitchen with large island is a wonderful place to entertain 🥂. Brand new washer/dryer, butlers pantry and mud room. Where the country meets the sea 🌊

Superhost

Home in Westhampton Beach

4.96 out of 5 average rating, 112 reviews

Brand new house with an all year round hot tub.

Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

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, 163 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.

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, 217 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.

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, 150 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.