Photo by Ellen Conroy

Wading River Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Wading River

Our top choices for Wading River holiday rentals

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

10.0 out of 10, Exceptional, (2)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
The price is AU$517
includes taxes & fees
27 Aug - 28 Aug
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

10.0 out of 10, Exceptional, (95)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is AU$1,145
includes taxes & fees
1 Sept - 2 Sept
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

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

9.6 out of 10, Exceptional, (133)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
The price is AU$1,537
includes taxes & fees
24 Aug - 25 Aug
Southampton cozy cottage by the beach

Spacious Home Located Close to Stony Brook!

6.8 out of 10, (18)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!

NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room

9.2 out of 10, Wonderful, (14)
"Beautiful property! Well stocked with essentials and perfect for our group with and age range o16 - 83"
NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room

Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

10.0 out of 10, Exceptional, (2)
"Everything was as pictured, and the whole place was very clean. It was a perfect stay for us, and we will come again soon!"
The price is AU$264
includes taxes & fees
1 Sept - 2 Sept
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

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

9.4 out of 10, Exceptional, (71)
"Wonderful time in a wonderful property. Megan the property owner was so very helpful."
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Hamptons Retreat

Hamptons Retreat

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
9.0 out of 10, Wonderful, (4)
"Large open first floor for a large family stay. Great back patio with a nice view of the river. Don't miss the morning swans. "
The price is AU$1,423
includes taxes & fees
4 Sept - 5 Sept
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (18)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
The price is AU$489
includes taxes & fees
24 Aug - 25 Aug
Walk to Beach 2BR Near Dining & Shopping

Dahlia by the Bay, walking distance from marina

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at this beautiful, spacious home. With plenty of room for all six of us spanning three generations, everyone from my youngest grandchild to myself was happy with the accommodations. The house was a great base for our family visit in the area. Don't hesitate to book this property—it was a great experience!"
Dahlia by the Bay, walking distance from marina

10 Bedroom Hampton House with a regulation size Pickleball court

9.8 out of 10, Exceptional, (30)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball court

Stunning Bayfront Views

9.8 out of 10, Exceptional, (36)
"House was exactly as described, excellent host and definitely went the extra mile to ensure we had a great stay. Cannot beat this location!"
Stunning Bayfront Views

Waterfront Westhampton Haven: Pool & Private Beach

9.0 out of 10, Wonderful, (2)
"The house has plenty of space and everything you will need for a great vacation. The best is the location which is on the bay and directly accross from Pikes Beach access. The property manager is very responsive. We had a wonderful stay. "
The price is AU$7,147
includes taxes & fees
1 Sept - 2 Sept
Waterfront Westhampton Haven: Pool & Private Beach

Family/pet friendly home in Hamptons w. Fire pit, pool, close to beaches/dining.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Check in was a breeze and the house was fully stocked with toiletries, towels, blankets, etc! Backyard was beautiful. We spent so much time in the pool and enjoyed our stay very much!"
Family/pet friendly home in Hamptons w. Fire pit, pool, close to beaches/dining.

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

10.0 out of 10, Exceptional, (185)
"Everything was amazing, the house is beautiful and very spacious, and the host was very friendly! I would 100% stay here again! "
The price is AU$1,475
includes taxes & fees
1 Sept - 2 Sept
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
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

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?

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.: This holiday home rental outside of Wading River has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Wading River?

Choose from 35 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.