House holiday rentals in Wading River

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Top-rated house rentals in Wading River

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Top guest favourite
A cozy living area is highlighted by wooden paneling and stone columns. Comfortable seating is provided by a large couch adorned with colorful patterns. A dining table set for four sits beside a bright pink tablecloth. A subtle floral artwork adds an inviting touch to the space.
Home in North Fork
4.98 out of 5 average rating, 189 reviews

Quiet Canoe Lake Cottage getaway

Peaceful private home on lush green resort like compound with historical outbuildings plus an additional studio apartment available for larger groups.Ideal for couples or a small family looking to explore the North or South forks of Long Islands East End and a short drive to the Hamptons famous beaches, villages and restaurants.A true garden lovers getaway with extensive flowers, vegetable and fruits and even our own apiary providing local raw honey. Near lots of wineries, restaurants and 2 miles from Tanger outlet mall shopping & top 5 rated Splish Splash Water Park. .Adjacent to the Peconic River for canoeing, kayaking, fishing or birding. The quiet winding country roads on either side of the river are a favorite destination for walking/joggers, biking and motorcycle touring. Riverhead town is a great central location and an easy drive to bay and ocean beaches. The area is still very much a rural farming area and a foodies delight with many pick your own fields,farmers markets, farm stands, wineries, horse, buffalo, and goat farms and even a potato vodka distillery and tasting room! We have an awesome Aquarium in town and our newly reopened Suffolk Theater with nightly live music and shows. Riverhead has lots of inexpensive small cafe style eateries for those on a budget.

Top guest favourite
Home in Milford
5 out of 5 average rating, 124 reviews

Jan/Feb longer stays avail! Inquire! New Firepit!

*Jan and Feb available for longer stays!Inquire!* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speed

Guest favourite
Home in The Hamptons
4.87 out of 5 average rating, 111 reviews

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!

Top guest favourite
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 The Hamptons
4.94 out of 5 average rating, 317 reviews

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 grouds are smoke-free.

Guest favourite
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 North Fork
4.91 out of 5 average rating, 104 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.

Top guest favourite
A well-lit bedroom features a spacious bed with decorative bedding, positioned against a soft blue wall. Natural light enters through large windows, adorned with sheer curtains. A compact dresser stands nearby, and an elegant table lamp adds functionality to the cozy space.
Home in Holbrook
4.91 out of 5 average rating, 298 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

Top guest favourite
A serene bedroom features a spacious bed with white linens, positioned against a wooden floor. Two shutters on adjacent windows allow soft light. A full-length mirror stands beside a dressing table, while a gentle light fixture hangs overhead. A calm art piece is displayed on the wall.
Home in Stony Brook
4.99 out of 5 average rating, 145 reviews

Cottage in the heart of Stony Brook Village

Totally renovated 100 year old charming but modern cottage steps from the Three Village Inn, Country House Restaurant, Stony Brook Village, Jazz Club, Sand St. Beach, Avalon Park, Carriage museum and the Long Island Music & Entertainment Hall of Fame. You will have the private upper floor of the cottage with a private entrance. There is a spacious porch and front yard with lounge chairs where you can watch the deer, chipmunks, birds, & rabbits. Short ride to Stony Brook University.

Guest favourite
A spacious farmhouse is showcased, featuring a welcoming porch with an American flag. The exterior is adorned with dark wooden shingles and large windows. Lush green lawn and well-maintained flower beds enhance the inviting curb appeal under a clear blue sky.
Home in North Fork
4.96 out of 5 average rating, 106 reviews

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Chic & Luxurious North Fork Farmhouse Retreat Set on a private 1-acre lot, this stylish farmhouse offers a pool, lounge areas, and refreshing ocean breezes. Just 1.5 hours from NYC, you’ll be minutes from beaches, wineries, farm stands, hiking, and golf. Inside, enjoy modern interiors, a full kitchen, and fast Wi-Fi. Perfect for families, couples, or friends, this retreat is ideal for a peaceful escape, remote work, or exploring wine country near the Hamptons and North Fork.

Superhost
A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.
Home in Mastic
4.85 out of 5 average rating, 129 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Top guest favourite
A dining area is presented featuring a dark wooden table surrounded by four white chairs. A decorative potted plant is centered on the table, complementing the modern decor. A doorway leads to a softly lit bedroom in the background.
Home in Port Jefferson
4.93 out of 5 average rating, 139 reviews

Port Jefferson Convenient, Cozy and Chic!

Bright, modern, newly renovated and landscaped space can sleep up to 6! Countless amenities including a kitchen with dishwasher, full size refrigerator. 3 bedrooms, 2 full baths, and common living space. Great for boaters or attending events in Port Jefferson, Stony Brook or anywhere on Long Island. We are a 1 minute drive or 10 minute walk from Port Jefferson Harbor and Ferry Dock. Centrally located on LI for easy access to LI rail road and bus routes.

Guest favourite
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.
Home in North Fork
4.94 out of 5 average rating, 144 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.

Top guest favourite
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.
Home in The Hamptons
4.99 out of 5 average rating, 151 reviews

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.

Popular amenities for house rentals in Wading River

Quick stats about house rentals in Wading River

  • Total holiday rentals

    Explore 30 holiday rentals in Wading River

  • Nightly prices starting at

    Wading River holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Wading River holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wading River rentals

  • 4.8 Average rating

    Wading River stays are highly rated by guests – averaging 4.8 out of 5!

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