A rocky shoreline with waves crashing onto the beach, a house on stilts, and a forested hillside in the background.

Search Holiday Homes in Wading River

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Wading River holiday homes

A living room with a sofa, a coffee table, a TV mounted on the wall, and a window with a view of houses outside.

1. Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (28 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is £384
includes taxes & fees
6 Oct - 7 Oct
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
A spacious living area with a fireplace, a wooden staircase, and large windows.

2. Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
8.0 out of 10, Very good, (10 reviews)
"Had such a nice weekend. Came for a friends wedding, on Labor Day weekend, the price was unmatched!! A few steps from the water. Down the street from the venue. Huge house. Beautiful kitchen. Very clean. Host was very communicative and accommodating. AC in every single room. Perfect weekend."
United States
Monika
The price is £555
includes taxes & fees
6 Oct - 7 Oct
Cozy beach hose minutes from Hamptons
A living room with a sofa, armchairs, a coffee table, and a rug.

3. Peaceful 3BR Garden Cottage Long Island Escape

Peaceful 3BR Garden Cottage Long Island Escape
Coram
10.0 out of 10, Exceptional, (1 review)
"Excellent host and peaceful getaway. I highly recommend!"
United States
Greg M.
The price is £388
includes taxes & fees
30 Sept - 1 Oct
Peaceful 3BR Garden Cottage Long Island Escape
A backyard with a swimming pool, outdoor furniture, and a house with solar panels.

4. Near the Hamptons - Private Pool, Jacuzzi Retreat

Near the Hamptons - Private Pool, Jacuzzi Retreat
Calverton
6.0 out of 10, (1 review)
"Upon arrival, there was a notice of non payment of almost 4000 from the electric company on the door so I was concerned I would lose electric. The grounds seemedover grown and unkept. There was no TV, no hot water in the kitchen with a brokenhot water knob which would have needed a wrench. Although it had in room air conditioners vented outside, they were taped in place with open air coming inside. One of the open areas actually had live tree vines coming inside which I pulled out. There was...
United States
Theresa M.
The price is £1,093
includes taxes & fees
30 Sept - 1 Oct
Near the Hamptons - Private Pool, Jacuzzi Retreat
Roger’s Beach

5. Prime location, walk to all, cozy cottage Westhampton Beach

Prime location, walk to all, cozy cottage Westhampton Beach
Westhampton Beach
10.0 out of 10, Exceptional, (3 reviews)
"Erica was very communicative and helpful. Very cozy with a great location."
United States
Chris J.
The price is £490
includes taxes & fees
2 Oct - 3 Oct
Prime location, walk to all, cozy cottage Westhampton Beach
A modern kitchen with a stainless steel refrigerator, a large island with bar stools, and pendant lighting.

6. Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
9.6 out of 10, Exceptional, (5 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is £437
includes taxes & fees
30 Sept - 1 Oct
Modern Vacation home. Close to The Hamptons
A covered outdoor seating area with a white door, a 'No Smoking' sign, and string lights.

7. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (9 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is £264
includes taxes & fees
5 Oct - 6 Oct
The Royal Suite - Ronkonkoma
A dining area with a table set for four, large windows, and a ceiling fan.

8. 3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (24 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is £477
includes taxes & fees
20 Oct - 21 Oct
3 Story Beach Waterview, 3 KING bed, golf putting green!
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

9. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is £1,288
includes taxes & fees
4 Oct - 5 Oct
Jacuzzi year-round - Villa Luz Private Home
A hot tub with two chairs, a pergola, and a wooden deck.

10. Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (33 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is £1,165
includes taxes & fees
29 Oct - 30 Oct
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
A modern living room with a grey sofa, round coffee table, and a white fireplace.

11. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (6 reviews)
"awesome house and awesome host"
United States
Matthew M.
The price is £2,035
includes taxes & fees
30 Sept - 1 Oct
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
A modern building with large windows overlooking a beach.

12. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (20 reviews)
"Views are incredible. Lucky enough to have had great weather before Memorial Day weekend! Our family loved it! Hot tub was wonderful."
United States
Donald J.
The price is £953
includes taxes & fees
12 Oct - 13 Oct
Beachfront Jacuzzi All Year - Black Swan Home
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

13. Elegant 5-Bedroom Hamptons Home with Private Pool

Elegant 5-Bedroom Hamptons Home with Private Pool
Hampton Bays
9.4 out of 10, Exceptional, (43 reviews)
"My family and I really enjoyed this home. Everything you can think of is provided for you. We would definitely stay here again!"
United States
Sarah A.
The price is £732
includes taxes & fees
30 Sept - 1 Oct
Elegant 5-Bedroom Hamptons Home with Private Pool
A rocky beach with clear water and a forested hillside in the background.

14. North Fork Fall Escape—Vineyards, Apple Picking & Greenport

North Fork Fall Escape—Vineyards, Apple Picking & Greenport
Mattituck
9.6 out of 10, Exceptional, (7 reviews)
"Stayed with several friends for a wedding in Jamesport"
United States
Glenn F.
The price is £1,081
includes taxes & fees
24 Oct - 25 Oct
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A modern living room with a grey sofa, a wooden coffee table, a flat-screen TV mounted on the wall, and a ceiling light fixture.

15. Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
8.8 out of 10, Excellent, (8 reviews)
"He’s an excellent hosts and his place is well worth it."
United States
Rowena V.
The price is £258
includes taxes & fees
7 Oct - 8 Oct
Peaceful private 2-bedroom house in Bayport. Amazing location!
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

16. Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (7 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is £983
includes taxes & fees
30 Sept - 1 Oct
Cozy Hamptons Escape 3BR Minutes From Beach!
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

17. Immaculate Waterfront 2 bedroom!

Immaculate Waterfront 2 bedroom!
Hampton Bays
10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is £429
includes taxes & fees
1 Oct - 2 Oct
Immaculate Waterfront 2 bedroom!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wading River Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Very good"
Rafael 1-night trip
Posted 2 hours ago
Hyatt Place Long Island East End

Find out more about Wading River

Wading River Holiday Homes information

Number of reviews
223
Accommodation
536 Holiday Homes
Lowest Price
£258
Highest Price
£2,035