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Wading River Holiday Rentals

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Holiday Rentals in Wading River

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (20)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

10.0 out of 10, Exceptional, (101)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is AU$798
includes taxes & fees
16 Oct - 17 Oct
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (20)
"Stay away"
The price is AU$423
includes taxes & fees
9 Oct - 10 Oct
Walk to Beach 2BR Near Dining & Shopping

10 Bedroom Hampton House with a regulation size Pickleball court

10.0 out of 10, Exceptional, (32)
"Cannot say enough good things. Unique, sprawling, beautiful property with more than enough room for a large group. Endless entertainment, great pool, walking distance from a few bars and restaurants. Great communication and accommodation from our host. Would recommend and rent again."
10 Bedroom Hampton House with a regulation size Pickleball court

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is AU$986
includes taxes & fees
9 Oct - 10 Oct
Modern Vacation home. Close to The Hamptons

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (191)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is AU$1,957
includes taxes & fees
17 Oct - 18 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (137)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful historic home in Stony Brook!

2.0 star property
8.4 out of 10, Very good, (15)
"Was a great place is a small town. Everything was clean and nice just wish there was a small sheer curtain in the bathroom where you shower. "
Beautiful historic home in Stony Brook!

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
8.4 out of 10, Very good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
The price is AU$1,382
includes taxes & fees
9 Oct - 10 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (50)
"The place was lovely and well appointed.. Beds were comfy. The spiral staircase was a bit tight to maneuver but location was perfect. It was a great spot for us, close to family in Sound Beach and Miller Place."
1856 Trading House w/ walk to water

Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

10.0 out of 10, Exceptional, (7)
"We had a great time, the house felt very cozy and it was spotless. Our host Robert was very nice and answered all of my concerns. I would definitely recommend this lovely house to anyone.I give it 5 stars."
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

9.6 out of 10, Exceptional, (23)
"This was the perfect location to enjoy the vineyards for my friend’s bachelorette party. Everyone had a comfy room and the space was very generous. Additionally the yard was massive and had ample seating. We had a great time and would definitely recommend this to all!"
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Stylish Five-Bedroom Oasis w/ Pool, Minutes from Beaches, Wineries & the...

10.0 out of 10, Exceptional, (1)
"the house is huge and well appointed. the outdoor space with the huge handsome awning set the stage. couch outside should be replaced but it's a small complaint in the big scheme of this house. updated bathrooms and bedrooms with four twin beds in total - very flexible living. pool outstanding, very deep and beautiful setting outside. could upgrade patio loungers but again not really detrimental and kind of charming"
Stylish Five-Bedroom Oasis w/ Pool, Minutes from Beaches, Wineries & the...

Summer getaway

9.0 out of 10, Wonderful, (14)
"Perfect location for a family holiday "
Summer getaway

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (73)
"Enjoyed our time. Thank you "
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Private beach on a fenced in property sunset views

10.0 out of 10, Exceptional, (12)
"We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay."
Private beach on a fenced in property sunset views

Charming 3 Bedroom Beach Front Cottage

2.0 star property
10.0 out of 10, Exceptional, (4)
"Stayed here while attending the Soundside Fest. Perfect location to be away from the busy Bridgeport area. The water is right there and it’s the perfect space for a weekend get away."
Charming 3 Bedroom Beach Front Cottage

Tranquil Stay

10.0 out of 10, Exceptional, (6)
"Great stay with family to see a couple of our son's shows at the Gateway Theatre. Thank you Andre for be a great host...!!!"
The price is AU$861
includes taxes & fees
22 Oct - 23 Oct
Tranquil Stay

Beach, Pool, Wine, Shopping!

10.0 out of 10, Exceptional, (73)
"The check-in process and communication couldn't have been easier. The property was clean, comfortable, and had everything we needed to enjoy ourselves. Conveniently located a walkable distance from Love Lane and a short drive from wineries (which is what brought us to the area)"
Beach, Pool, Wine, Shopping!
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.
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Top Wading River Hotel Reviews

Find out more about Wading River

Find out more about Wading River

Everything you need to know about Wading River holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wading River holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wading River holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wading River holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wading River. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wading River holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wading River holiday rentals we have selected for you start as low as AU$423 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wading River rentals

At Expedia, we put the best Wading River holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wading River rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wading River holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wading River. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Spacious Home Located Close to Stony Brook!: This holiday home rental outside of Wading River offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 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 34 Expedia holiday rentals in Wading River for a memorable holiday.

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

Wading River Landing and Deep Pond are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Wildwood State Park and Great Rock Golf Club.

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.