
House holiday rentals in Wading River
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Top-rated house rentals in Wading River
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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.

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.

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

“The Lighthouse” A Beach Cottage by the Sea!
Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Joyful Beach House, viewing The Great South Bay
Amazing Great South Bay view with access to Shorefront and Rider Parks. This Ranch has an unobstructed view of the Shorefront Band Shell. Watch concerts and sunsets from the comfort of your patio. Walk down to the Patchogue Beach Club and enjoy the pool and beach. This open-concept home has 2 bedrooms, one bath, a remodeled bathroom, and a kitchen. The kitchen has stainless steel appliances, a farm sink, and a butcher block countertop with natural lighting that will brighten the home.

Harborfront Star
Hang up your car keys and your worries and come visit this beautiful, stylish, coastal gem. Everything that Port Jefferson Village has to offer -- the marina, Harborfront Park, restaurants, clubs, shops, galleries, skating rink, green market, Danfords -- is all within easy walking distance. So come enjoy being in the middle of the action -- and the cool breezes off Long Island Sound -- at the Harborfront Star. We are dog friendly and have a pet fee of $65 per dog (max of 3 dogs).

PICTURE PERFECT SOUTHAMPTON HOME-
Picture Perfect 3 bedroom 1.5 Bath Cottage located in the heart of Southampton. The home is conveniently located close to Southampton, Bridgehampton and Sag Harbor towns. Additionally, there is close access to both Bay and Ocean Beaches. The Newly renovated home gives you a peaceful and serene feeling everyday. Dogs are accepted on a case by case basis. Cats are not permitted. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

The Sandpiper
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Modern Farmhouse Steps to Beach & Love Lane
Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

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.

Luxury modern farmhouse with heated pool & hot tub
*pool closed November to end of April This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

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 Wading River house rentals
House rentals with a pool

Designer Home w/ Heated, Salt-Water Pool

Spectacular Southampton Retreat!

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Classic Southampton Village Home w/ Pool

Stunning Farmhouse in NoFo I Heated Pool, Wineries

GOOD VIBEZ HOUSE! Mini Golf+Pool+Hot Tub+Game Room

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)
Weekly house rentals

Port Jeff Home near Stony Brook University SBU

3BR/2.5BA: vineyard views, open layout

Adorable Beach House on LI Sound

Cottage with Seashells

Private 1-Bdrm Apt in West Haven

Classic Coastal Retreat: Larsson House

Cozy Beach Cottage

Bright, Stylish & Cozy Suite
Private house rentals

Coastal Farmhouse Getaway • LI Wine Country

Waterfront Home w Private Beach & Firepit

Historic Home on the Harbor!

Stunning Guest Suite in Medford

5 Star Branford Cozy Cottage

3 bedroom cottage rental

Cozy Private Suite Near Train to NYC

Trendy Ranch in Bellport Village
Quick stats about house rentals in Wading River

Total holiday rentals
Explore 40 holiday rentals in Wading River

Nightly prices starting at
Wading River holiday rentals start at $84 NZD per night before taxes and fees

Verified guest reviews
Over 1,160 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Wading River holiday rentals include Wi-Fi 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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- Rentals with a fire pit Wading River
- Pet-friendly rentals Wading River
- Rentals with a patio Wading River
- Family-friendly rentals Wading River
- Rentals with beach access Wading River
- Rentals with outdoor seating Wading River
- Rentals with a washing machine and dryer Wading River
- Waterfront rentals Wading River
- Rentals with a fireplace Wading River
- House rentals Suffolk County
- House rentals New York
- House rentals United States
- Yale University
- Jones Beach
- Fairfield Beach
- Cooper's Beach, Southampton
- Southampton Beach
- Robert Moses State Park Beach
- Ocean Beach Park
- Sunken Meadow State Park
- Jones Beach State Park
- Hammonasset Beach State Park
- Long Island Aquarium
- Powder Ridge Mountain Park & Resort
- Mount Southington Ski Area
- Sherwood Island State Park
- Yale University Art Gallery
- Sleeping Giant State Park
- Compo Beach
- Dunewood
- Orient Beach State Park
- East Hampton Main Beach
- Meschutt Beach
- Ditch Plains Beach
- Wölffer Estate Vineyard
- UBS Arena




