Photo by Ellen Conroy

Holiday Rentals in Wading River

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Wading River

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

Westhampton Beach
10.0 out of 10, Exceptional, (194)
"House was more then I can imagine , host was great , house literally have anything you forgot at home . "
United States
Isiah L.
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Walk to Beach 2BR Near Dining & Shopping

Rocky Point
6.8 out of 10, (23)
"The home is cute and cozy--located close enough to attractions and restaurants but off the beaten path."
United States
Lori M.
The price is €210
includes taxes & fees
12 Nov - 13 Nov
Walk to Beach 2BR Near Dining & Shopping

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Jamesport
10.0 out of 10, Exceptional, (8)
"Found this location and seemed too good to be true when we had an unplanned trip that we were able to take. House was great and location really worked for our needs. Food and winery recommendations were spot on and getting around was easy. Thanks for helping us make some great memories in NY!"
United States
Brent M.
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Bayport
10.0 out of 10, Exceptional, (88)
"Great location. Very peaceful. Great house"
United States
Richard D.
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Charming 3 Bedroom Beach Front Cottage

2.0 star property
Milford
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."
United States
Sarah W.
Charming 3 Bedroom Beach Front Cottage

Cozy Country Cottage #2

Miller Place
9.0 out of 10, Wonderful, (14)
"We were looking for a property close to my in-laws where we could bring our 2 pups and we found this wonderful home. The cottage is much bigger than expected and beautifully furnished and well-equipped. Full size washer and dryer with newer appliances and a fenced in yard for the dogs. AC also worked very nicely during a very warm week. Plenty of towels, sheets, and roll away bed made our stay perfect. Definitely would stay again!"
United States
Robin M.
The price is €303
includes taxes & fees
9 Nov - 10 Nov
Cozy Country Cottage #2

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

Hampton Bays
9.6 out of 10, Exceptional, (142)
"Had a lovely time at our stay! Only regret was that we couldn’t stay longer, there were so many amenities we couldn’t take full advantage of. Such a beautiful property!"
United States
Gina K.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Modern Vacation home. Close to The Hamptons

Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is €591
includes taxes & fees
17 Nov - 18 Nov
Modern Vacation home. Close to The Hamptons

Beautiful historic home in Stony Brook!

2.0 star property
Stony Brook
8.2 out of 10, Very good, (20)
"Thank you Great Location Would book again"
United States
M M.
Beautiful historic home in Stony Brook!

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Eastport
9.6 out of 10, Exceptional, (34)
"We had a lot of fun and created some nice memories"
United States
Scott T.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

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

Center Moriches
10.0 out of 10, Exceptional, (105)
"2 friends and I rented John's place for a mini reunion. It was perfect for us. Very clean, very cutely decorated, loved the access to the bay, and sitting on the swings overlooking the bay. Geat deck to eat and relax. Though we didn't meet our host, he answered all of our communications in a timely fashion."
United States
Ruth E.
The price is €686
includes taxes & fees
7 Dec - 8 Dec
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

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

Hampton Bays
9.4 out of 10, Exceptional, (75)
"As always everything was excellent, This is our third stay at this property and we are booked for 2026"
United States
Michael R.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Centereach
10.0 out of 10, Exceptional, (44)
"Great experience and stay!"
United States
Annie P.
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

Stony Brook
6.0 out of 10, (2)
"Very comfortable and welcoming Only problem was only one bathroom door closed the other one appeared to be in disrepair Other then that all was well"
United States
Kathleen
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

Private 1 bedroom apt in a quiet neighborhood, close to all!

Centereach
9.6 out of 10, Exceptional, (26)
"Property is close to Stony Brook University and was very comfortable and clean. Would definitely stay here again."
United States
Erik
The price is €219
includes taxes & fees
10 Nov - 11 Nov
Private 1 bedroom apt in a quiet neighborhood, close to all!

Newly renovated Private bedroom near Stony Brook University

2.0 star property
Stony Brook
6.0 out of 10, (1)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is €205
includes taxes & fees
8 Nov - 9 Nov
Newly renovated Private bedroom near Stony Brook University

Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

Hampton Bays
9.8 out of 10, Exceptional, (19)
"The house was clean and the location was magnificent. Jake was great, offered us early check in and late check out. The neighborhood was lovely, walked my pup and admired all of the beautiful homes. Definitely will stay there again. "
United States
Angela G.
Private Waterfront on Peconic Bay in Hampton Bays - Southampton - Fall Special!

Private One Bedroom Apartment with full kitchen, living room and full bath.

Ridge
9.4 out of 10, Exceptional, (8)
"Tammy was a lovely host. She provided very detailed instructions on how to get to the Vrbo, parking location, and access in advance. Vrbo was just as pictured too! "
United States
Kristyn R.
Private One Bedroom Apartment with full kitchen, living room and full bath.

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Mastic Beach
10.0 out of 10, Exceptional, (4)
"The property was very relaxing, clean, and well stocked, and the hosts were incredibly accommodating!"
United States
Andrea D.
The price is €295
includes taxes & fees
11 Nov - 12 Nov
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
Calverton
8.4 out of 10, Very good, (7)
"A fantastic location, and would certainly stay again! The bed was a bit hard but we all like something different. "
United States
Ethan L.
The price is €569
includes taxes & fees
21 Nov - 22 Nov
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
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

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, apart-hotels, 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 favorite 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 depends 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 €205 per night. Entering your travel dates in the search wizard you might find 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?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr: This holiday home rental outside of Wading River offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and 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.