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Wading River Holiday Rentals

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Holiday Rentals in Wading River

Beachfront Romance: Rustic Home w/ Private Beach
On the beach
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, (39)
"The house is small but it has everything you need. The ocean was lovely to watch and good scavenging for rocks and sea glass. Very private place. My pup and I had a good time!"
Beachfront Romance: Rustic Home w/ Private Beach
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
On the beach
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
9.8 out of 10, Exceptional, (50)
"Couldn't say enough positive's about this stay. The owner was very responsive from before it was even booked all the way through the stay and after. The house has a gorgeous view and it's cozy for a nice weekend away. We will definitely be back."
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
Interior
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
8.8 out of 10, Excellent, (13)
"4 families came from CA for a graduation celebration. Enough room and beds for all 10 of us. Easy access to lake. Backyard is huge, had fun playing badminton and volleyball. Also lit a fire at the fire pit one night. Managers were very responsive to our questions and requests There is a projector and we were able to watch movies at night. Pretty cool. Had a great stay."
The price is NZ$1,674
per night
1 Jun - 2 Jun
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
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North Fork Escape Near Wineries, Beaches And Hamptons
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Sun-loungers, beach towels
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (147)
"In town for a wedding - a large, convenient location that fulfilled the needs we had for that stay."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Airstream Art Studio Sculpture/Nature Preserve
Interior
Airstream Art Studio Sculpture/Nature Preserve
10.0 out of 10, Exceptional, (2)
"This place was one of the best parts of my stay on LI. It is tucked away on a beautiful stretch of property but still close to central locations making it easy to go out for provisions. I "gifted" myself a stay here as a single-mother and former art maker. This was the first time I painted in 10+ years, the environment and the energy filled my cup to overflowing! Thank you so much for having this space available. I will return."
The price is NZ$387
per night
7 Jun - 8 Jun
Airstream Art Studio Sculpture/Nature Preserve
Location and views! Located directly on Shinnecock Bay!
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (12)
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
On the beach, sun-loungers, beach towels
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
10.0 out of 10, Exceptional, (46)
"Traveling with family and dog... private walk to the beach, stylish but simple, comfortable beds, clean and organized, responsive management... 2 bedrooms downstairs, one entire 2nd floor master bedroom / entertaining space upstairs, and an attached 'cottage' king studio that is attached to the main house."
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
Beach nearby, sun-loungers, beach towels
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
10.0 out of 10, Exceptional, (9)
"My wife, two children (28, 30) and I came to town for a couple of family events and stayed 11 days. If I had to sum up our time in a single word, I would use "Wonderful"! The check-in process was a breeze. The open floor plan made it feel like you were part of everything going on whether cooking in the kitchen, sitting at the table or on the couch. We spent time every night in the game room shooting pool, playing ping pong and foosball together. The only reason the TV was on at all was for a...
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
Gorgeous private Hamptons house with pool and volleyball court
Outdoor pool
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, (7)
"This place was nice and roomy for our family of 8 plus 3 littles kiddos. Pretty clean as well. I gave listing accuracy a 5 because it is accurate but that may be because it doesn't tell you much. We were a little short on towels, many light bulbs were burnt out or just missing. We replaced some (they were there) and moved others to balance out the light. No kitchen linens, short on bath towels, short on paper towels and definitely not enough TP. 3 partial rolls and 1 bathroom had none so we had...
Gorgeous private Hamptons house with pool and volleyball court
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
Property grounds
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
9.6 out of 10, Exceptional, (9)
"my family and i grew up coming to hampton bays - and while myself and my parents have moved away - a family wedding brought us back to the area and we were so happy to stay local in this perfect home. it felt great to be back in the old neighborhood and not have to be cramped at my brothers home just a short 5 minute drive away. i hope we can stay again during our next trip!"
Charming Hampton Bays Home 5 Mi to Cooper’s Beach
Private 1 bedroom apt in a quiet neighborhood, close to all!
Fridge, microwave, oven, stovetop
Private 1 bedroom apt in a quiet neighborhood, close to all!
9.4 out of 10, Exceptional, (11)
"Thank you very much for being so accommodating with our stay! It was very clean, had all the essentials plus extra and we really liked how we had our own private patio. Will definitely be staying again in the future!"
The price is NZ$390
per night
10 Jun - 11 Jun
Private 1 bedroom apt in a quiet neighborhood, close to all!
Charming Cape Close to the Ocean
Property grounds
Charming Cape Close to the Ocean
5.2 out of 10, (5)
"Great area and good rental"
Charming Cape Close to the Ocean
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
Exterior
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
10.0 out of 10, Exceptional, (75)
"Great location. Pristine beach with hardly anyone else on the beach (mid May). No shampoo or conditioner in bathrooms as reported. The house needs a bit of TLC. Could be a bit cleaner. There was sand on the floor in the master bedroom upon our arrival. It seemed like there was white dog hair on the bedspread. I dont have a dog. The dishwasher seemed like it was working but was not getting the dishes clean. I think it is time for a new dishwasher."
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Outdoor pool, a heated pool
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (22)
"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
8.6 out of 10, Excellent, (8)
"The property was clean and large and the outdoor space made for a fun gathering place, especially for the children in our group. It would have been nice to have dedicated spaces to hang towels and clothes, especially as we had so many people staying. The hosts were friendly and accommodating and we would stay again."
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
HAMPTON BAYS HOME MINUTES FROM SOUTHAMPTON VILLAGE, SHINNECOCK BAY, OCEAN...
Property grounds
HAMPTON BAYS HOME MINUTES FROM SOUTHAMPTON VILLAGE, SHINNECOCK BAY, OCEAN...
10.0 out of 10, Exceptional, (1)
"The house was perfect and clean. We really enjoyed the screened in patio."
HAMPTON BAYS HOME MINUTES FROM SOUTHAMPTON VILLAGE, SHINNECOCK BAY, OCEAN...
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
Fridge, microwave, oven, stovetop
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
9.8 out of 10, Exceptional, (16)
"This property was just what my family and I were looking for. A quaint and quiet house with a small town feel. We stayed for NYE hoping to get away from the loud chaos we’re typically faced with at home and this location fit the bill. Pros: I’m not sure how this changes in the summer months but things were mostly quiet. There are restaurants, coffee, and food shopping all within a 5 minute drive. The home itself is pretty small, so for the 4 of us- husband, 17y/o, 9 y/o, and myself, it was...
Beautiful remodeled 2 bedroom home — 5 min from the beach! 20 percent for week
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!
Smart TV, fireplace, smart speakers
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!
9.8 out of 10, Exceptional, (11)
"Great location to visit family on the South Shore. Easy access to town/restaurants. Very responsive host! We’ll be back."
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!
3 Story Beach Waterview, 3 KING bed, golf putting green!
Interior
3 Story Beach Waterview, 3 KING bed, golf putting green!
10.0 out of 10, Exceptional, (8)
"My family and I, rented this beautiful BNB to stay in while in town for my Grandmothers 90th Birthday. The home was exactly as pictured on the site, it was by far the cleanest and best taken care property that we have rented through VRBO! We were beyond impressed by the Host Eddie and his home! We willlllll be back!"
The price is NZ$906
per night
3 Jun - 4 Jun
3 Story Beach Waterview, 3 KING bed, golf putting green!
Don't see what you're looking for?
See all available properties in Wading River
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Wading River you may be interested in

Beachfront Romance: Rustic Home w/ Private Beach
On the beach
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, (39)
"The house is small but it has everything you need. The ocean was lovely to watch and good scavenging for rocks and sea glass. Very private place. My pup and I had a good time!"
Beachfront Romance: Rustic Home w/ Private Beach
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
On the beach
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
9.8 out of 10, Exceptional, (50)
"Couldn't say enough positive's about this stay. The owner was very responsive from before it was even booked all the way through the stay and after. The house has a gorgeous view and it's cozy for a nice weekend away. We will definitely be back."
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
Hyatt Regency Long Island
Exterior
Hyatt Regency Long Island
3.5 star property
8.0 out of 10, Very good, (1003)
"I had surgery the of my stay at the hotel. Staff was extremely helpful and accommodating. Room was immaculate. "
The price is NZ$333
per night
16 Jun - 17 Jun
Hyatt Regency Long Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wading River holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wading River. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wading River. Seeing all the best attractions is bound to make you fall in love with Wading River. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wading River short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Wading River?

Yes, there are holiday rentals close to the most popular sights in Wading River, or you can select a more secluded option if you're looking for a relaxing stay. The spas and wineries are several reasons why visitors like Wading River. While you're here, grab a bite or have a drink at the restaurants.

What are some of the best holiday rentals that Wading River has to offer?

Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres : This holiday home rental outside of Wading River is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Wading River?

Choose from 39 Expedia holiday rentals in Wading River for a memorable holiday.

What’s there to see and do in Wading River?

Wildwood State Park and Wading River Landing are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Duck Pond Park and Police Officers Memorial Park.

What’s a holiday rental in Wading River like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wading River. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for family trips or small group gatherings.

Recent reviews of Wading River properties
Expedia verified reviews

Homewood Suites by Hilton Ronkonkoma

Homewood Suites by Hilton Ronkonkoma

5/5 Excellent
"Thanks for the super easy check in."
A verified traveller stayed at Homewood Suites by Hilton Ronkonkoma
Posted 1 day ago
Homewood Suites by Hilton Ronkonkoma