Photo by Ellen Conroy

Wading River Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation 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. "
$534 nightly
The price is $610
Nov 2 - Nov 3
Total with taxes and fees
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"
$242 nightly
The price is $276
Oct 9 - Oct 10
Total with taxes and fees
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"
$562 nightly
The price is $642
Oct 9 - Oct 10
Total with taxes and fees
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."
$1,117 nightly
The price is $1,276
Oct 17 - Oct 18
Total with taxes and fees
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. "
$789 nightly
The price is $901
Oct 9 - Oct 10
Total with taxes and fees
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)
"My best friend and I wanted to get out of the city with our pups for a long weekend, and this was absolutely the perfect place to do that! Robert was accommodating, kind, and quick to respond. And the neighborhood/community is adorable, friendly, and low key. Being literally steps from the beach was beyond amazing, and being able to sit on the front patio and get the breeze/view was unmatched! Can’t wait to come back again! "
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...!!!"
$491 nightly
The price is $561
Oct 22 - Oct 23
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wading River vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wading River vacation 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 low season months. For more hustle and bustle, you may prefer to visit Wading River in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $276 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wading River rentals

At Expedia, we put the best Wading River vacation 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 vacation.

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 vacation rentals in Wading River?

Yes, you can find vacation rentals close to the most popular attractions in Wading River, or you can choose a more remote option if you'd like a relaxing place to 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's the top vacation rental that Wading River has to offer?

Spacious Home Located Close to Stony Brook!: This vacation home rental near Wading River offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Wading River?

Choose from 34 Expedia vacation rentals in Wading River for a memorable vacation.

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 vacation rental in Wading River like?

Vacation rentals are private properties you can stay in for short or long periods in Wading River. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.