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House vacation rentals in Wading River

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Top-rated house rentals in Wading River

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Top guest favorite

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, 183 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.

An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.

Home in Shirley

4.98 out of 5 average rating, 208 reviews

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

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 Sagaponack

4.94 out of 5 average rating, 308 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.

An aerial view showcases a coastal neighborhood with homes situated along a sandy beach. Vibrant blue waters and marshlands surround the area, emphasizing its seaside location. The arrow points to the property's location within the community, illustrating proximity to the beach.

Home in Milford

4.96 out of 5 average rating, 226 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Top guest favorite

An aerial view captures a private guest house surrounded by lush green landscaping. Outdoor furniture is arranged around a small table, complemented by two sun beds. A barbeque grill is visible near the house, with vibrant flowers accentuating the backyard space.

Home in Brookhaven

4.96 out of 5 average rating, 194 reviews

Beautiful & Independent Guest House near the water

Welcome to our beautiful yet very private guest house in Brookhaven. You are walking distance from the Deer Run Farm (fresh eggs every morning), Post-Morrow Nature Trails and a short drive to Bellport Village Historic District. We are also very close to Wine Country, The Hamptons & Fire Island. We offer all the accommodations you might need for longer stays Washer & Dryer; Dishwasher; High Speed internet and TVs with all the premium channels. EV Charger available (Tesla - Fees applies).

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

4.97 out of 5 average rating, 159 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

An aerial view captures a spacious backyard featuring a heated saltwater swimming pool surrounded by lounge chairs. The meticulously maintained lawn is dotted with trees and flowering plants, leading to a paved pathway. A deck with outdoor seating and an umbrella creates inviting outdoor spaces.

Home in Manorville

4.97 out of 5 average rating, 259 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Ultimate house with 4 Bds, 3 Baths, finished basement with entertainment area and gym. Minutes from the Hamptons and North Fork. Everything for your rest in any weather and season. Yamaha piano, Japanese massage chair, karaoke, drum set, electric guitars, ping pong, fossball and pool tables,board games. Fully landscaped backyard with flowering plants, outdoor lights. 2 BBQ areas, Gazebo with fireplace and projector. Easy access to beaches, restaurants, farms, vineyards and shopping.

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

4.95 out of 5 average rating, 133 reviews

⭐️Modern Farmhouse Long Island Wine Country🍷

Long Island’s North fork Long Island Wineries. Luxurious, clean , modern peaceful farmhouse. Top of the line fully stocked kitchen, stainless steel appliances, granite countertops. Keurig Coffee maker, Tea, Hot Coco. Coffee grinder . 2 fully stocked Spa like bathrooms w/ luxurious towels .4 Lg. Bedrooms. w/ luxurious linens .Cozy fireplace in Living room. Spacious dining room. Close to Farms, Wineries, Corn Mazes, Haunted Attractions, Sunflower Mazes. Pumpkin 🎃 Apple 🍎 Picking

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.

4.89 out of 5 average rating, 117 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 favorite

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 Westhampton Beach

4.99 out of 5 average rating, 142 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.

A charming red cottage is set among lush greenery, showcasing a manicured lawn leading to the porch. The house features a rustic stone chimney and a welcoming front porch adorned with white railings. Nearby, a small structure complements the main home with a rounded window.

Home in Port Jefferson

4.8 out of 5 average rating, 336 reviews

The Hilltop Harborview

Guests will immediately walk past spacious hot tub into a comfortable sunroom where you’ll watch the most colorful, water view sunsets Long Island has to offer! This one of a kind offers a sprawling layout that has 3 queen size bedrooms and 1 king . We can also provide an air mattress for an additional guest. There is a kitchen equipped with stove, oven, dishwasher and washer and dryer! This beautiful walking Village has so much to offer!

An inviting waterfront deck is displayed, featuring two lounge chairs with striped fabric and a small table. A fire pit sits nearby, surrounded by a clear view of the bay, where sailboats are gently anchored. Lush greenery lines the horizon, enhancing the serene atmosphere.

Home in Centerport

4.94 out of 5 average rating, 156 reviews

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC"! Welcome to Long Island's Gold Coast! Enjoy stunning beachfront views from this charming home. You may spot the bald eagle family that lives around the corner! Local spots to visit include the Vanderbilt Mansion and Planetarium, Caumsett State Park Preserve, Del Vino Vineyards, Paramount Theatre, Downtown Huntington, Northport Main Street shops and restaurants, and more!

Vacation rentals for every style

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Popular amenities for Wading River house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A patio is shown with a wooden table and a dark wicker chair overlooking a scenic view. A clear sky with scattered clouds is visible in the background, along with open fields and distant structures. Utility poles line the road, adding context to the setting.

Home in Patchogue

4.93 out of 5 average rating, 127 reviews

Joyful Beach House, viewing The Great South Bay

Top guest favorite

Home in North Fork

4.97 out of 5 average rating, 207 reviews

Private Oasis W/Stunning Vinyard and Pool Views

A contemporary home is depicted with a clear blue pool in the foreground, surrounded by a spacious wooden deck. Lush greenery and autumn foliage frame the property, while sliding glass doors provide views of the interior.

Home in Hampton Bays

4.94 out of 5 average rating, 132 reviews

Peaceful Retreat in Immaculate Architect’s House

The outdoor area features a spacious pool surrounded by a neat stone patio. Lounge chairs are arranged neatly by the water, while lush greenery and mature trees provide shade and privacy. A sunlit house with large windows is visible in the background.

Home in Westhampton Beach

4.92 out of 5 average rating, 104 reviews

Hamptons Oasis: pool, grill, lush landscape

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

4.96 out of 5 average rating, 111 reviews

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

The exterior of the home presents a charming shingle-style design, featuring multiple large windows. A spacious patio with outdoor seating surrounds a clear blue pool, complemented by a large umbrella for shade. Lush greenery provides privacy along the property line.

Home in Southampton

5 out of 5 average rating, 47 reviews

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

A spacious outdoor pool is surrounded by a stone patio, nestled within a serene environment of tall trees. The pool features a diving board and is complemented by nearby planters. A main house can be seen in the background, enhancing the tranquil setting.

Home in Stamford

4.96 out of 5 average rating, 252 reviews

Midcentury Modern ZenHouse Sculptor Studio

Home in Southampton

4.93 out of 5 average rating, 109 reviews

Classic Southampton Village Home w/ Pool

Weekly house rentals

Top guest favorite

The exterior of the historic house is depicted, showcasing the two-story structure with gray shingle siding. A set of steps leads to the front door, adorned with an American flag. Surrounding greenery adds a natural touch to the property.

Home in Port Jefferson

5 out of 5 average rating, 61 reviews

The Historic 1813 House

A two-story blue house is set in a well-maintained yard with green grass and neatly trimmed hedges. A double garage doors are visible on the left, and a front porch with steps leads to the main entrance, framed by decorative shrubs.

Home in Center Moriches

4.94 out of 5 average rating, 35 reviews

Peaceful and Bright 4 Bedroom Getaway Home

A calm beach scene is depicted at sunset, with vibrant colors reflecting off the water's surface. The sandy shore stretches into the distance, bordered by gently lapping waves. Soft clouds create a gradient of hues in the evening sky, enhancing the tranquil atmosphere.

Home in Riverhead

4.85 out of 5 average rating, 26 reviews

The Perfect Bay House Escape

A living room is highlighted by a cozy sofa draped with a light throw. A glass coffee table sits atop a soft rug. A fireplace is set within a white mantel, complemented by plants and framed art that add a touch of character.

Home in Bellport

4.87 out of 5 average rating, 93 reviews

The Stella ~ Bellport Beach & Wetlands

Top guest favorite

The beachfront home features a wrap-around balcony and large windows that provide views of the shore. The exterior is surrounded by a stone wall and sandy beach, with a staircase leading down to the water from the deck.

Home in North Fork

5 out of 5 average rating, 14 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

Top guest favorite

A modern living room features a light-colored sectional sofa adorned with soft cushions. Mounted on the wall, a large television displays a fireplace scene. Light wood shelves hold decorative items, while large windows allow natural light to fill the space.

5 out of 5 average rating, 18 reviews

Beautiful Home

A modern living area is displayed with light-colored furniture, including two patterned armchairs, a round leather ottoman, and a cozy seating arrangement. A fireplace is framed by built-in shelves showcasing decorative items and a large framed photograph hangs above, complementing the bright ambiance.

Home in East Quogue

5 out of 5 average rating, 10 reviews

Charming, Modern Hamptons Gem

A dining area is showcased with a round table surrounded by four teal chairs. Large sliding doors reveal bay views, framed by sheer white curtains. A rug with black and white stripes lies beneath the table, complementing the light hardwood flooring and wall-mounted artwork.

Home in Shirley

4.95 out of 5 average rating, 40 reviews

Waterfront Designer Stay • Sunsets • Near Beach!

Private house rentals

A charming two-story house with wooden siding is set within a landscaped yard featuring lush green grass. Sunlight reflects off the windows, and a small balcony is visible on the upper level. A patio area with outdoor seating is located to the side.

Home in Westhampton Beach

4.98 out of 5 average rating, 40 reviews

Walk to the village! Modern beach house

A spacious beachfront property is showcased, featuring a well-maintained lawn and a patio area with outdoor seating. The ocean is visible in the background, providing serene water views. The home is characterized by its coastal architecture and nearby neighboring structures.

Home in Branford

4.95 out of 5 average rating, 39 reviews

Adorable Beach House on LI Sound

Top guest favorite

An aerial view captures the heated saltwater pool surrounded by a spacious patio. Lounge chairs and shaded seating areas are arranged near the pool, with outdoor furniture positioned for relaxation. Lush greenery and a landscaped garden frame the space, providing a serene environment.

Home in Yaphank

5 out of 5 average rating, 38 reviews

Long Island Getaway w/ Heated Pool & Lake

Top guest favorite

The kitchen features modern appliances set against white cabinetry, complemented by black bar stools. An outdoor gathering area showcases a circular fire pit surrounded by black Adirondack chairs, with waterfront views in the background. A cozy bedroom displays a large bed with decorative pillows and natural light filtering through the window.

Home in Stratford

5 out of 5 average rating, 6 reviews

Charming Riverview Home *Near Train & I-95

A charming two-story house features a light-colored exterior with dark accents. A welcoming front porch leads to the entrance, and a grassy yard surrounds the property, creating a peaceful atmosphere. Nearby trees and accessible parking are visible, enhancing the inviting setting.

Home in Mastic Beach

5 out of 5 average rating, 12 reviews

Newly Renovated Home in Mastic Beach!

Top guest favorite

A bright kitchen features sleek white cabinetry and stainless steel appliances. A circular table sits centrally, complemented by a small potted plant. Natural light filters through the patterned window treatment, enhancing the modern atmosphere of the space.

Home in Westhampton Beach

5 out of 5 average rating, 22 reviews

Charming Home in WestHampton Beach

Top guest favorite

A blooming tree with pink flowers is positioned in front of a small white cottage. The driveway is newly paved, surrounded by a grassy area. Tall trees provide a natural backdrop, while a wooden fence lines the property, enhancing the cottage's privacy.

Home in North Fork

5 out of 5 average rating, 20 reviews

Oak Street Cottage

A covered patio area showcases comfortable outdoor seating, with a soft-toned sectional sofa facing the water. Lounge chairs are positioned nearby, offering unobstructed views of the tranquil ocean under a cloudy sky. The deck is lined with protective railings for safety.

Home in Hampton Bays

4.85 out of 5 average rating, 80 reviews

Hamptons Oceanfront Oasis

Quick stats about house rentals in Wading River

Total rentals
40 properties
Nightly prices starting at
R886 ZAR before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Destinations to explore