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

Holiday Homes in Wading River

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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 €449
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 €660
includes taxes & fees
6 Oct - 7 Oct
Cozy beach hose minutes from Hamptons
Beach

3. BEACHFRONT MANSION PRIVATE PATH TO PRIVATE BEACH

BEACHFRONT MANSION PRIVATE PATH TO PRIVATE BEACH
Shoreham
9.8 out of 10, Exceptional, (10 reviews)
"Great house for our large family. Perfect location. Loved the beach. Only thing that was not clear was pool access - unfortunately it was closed when we were there."
Canada
Kim V.
BEACHFRONT MANSION PRIVATE PATH TO PRIVATE BEACH
A living room with a sofa, armchairs, a coffee table, and a rug.

4. 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 €452
includes taxes & fees
30 Sept - 1 Oct
Peaceful 3BR Garden Cottage Long Island Escape
A modern kitchen with a stainless steel refrigerator, a large island with bar stools, and pendant lighting.

5. Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
9.6 out of 10, Exceptional, (5 reviews)
The price is €510
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.

6. 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 €308
includes taxes & fees
5 Oct - 6 Oct
The Royal Suite - Ronkonkoma
Roger’s Beach

7. 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 €575
includes taxes & fees
1 Oct - 2 Oct
Prime location, walk to all, cozy cottage Westhampton Beach
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

8. 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 €1,506
includes taxes & fees
4 Oct - 5 Oct
Jacuzzi year-round - Villa Luz Private Home
A backyard with a swimming pool, outdoor furniture, and a house with solar panels.

9. 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 €1,274
includes taxes & fees
30 Sept - 1 Oct
Near the Hamptons - Private Pool, Jacuzzi Retreat
A dining area with a table set for four, large windows, and a ceiling fan.

10. 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 €556
includes taxes & fees
20 Oct - 21 Oct
3 Story Beach Waterview, 3 KING bed, golf putting green!
A modern building with large windows overlooking a beach.

11. 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 €1,114
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.

12. 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 €855
includes taxes & fees
30 Sept - 1 Oct
Elegant 5-Bedroom Hamptons Home with Private Pool
A hot tub with two chairs, a pergola, and a wooden deck.

13. 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 €1,525
includes taxes & fees
27 Oct - 28 Oct
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
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.

14. 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 €301
includes taxes & fees
6 Oct - 7 Oct
Peaceful private 2-bedroom house in Bayport. Amazing location!
A restaurant with wicker furniture and large windows overlooking the ocean at sunset.

15. North Fork Fall Escape - Vineyards visits - Wineries • Apple Picking • Greenport

North Fork Fall Escape - Vineyards visits - Wineries • 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 €1,261
includes taxes & fees
24 Oct - 25 Oct
North Fork Fall Escape - Vineyards visits - Wineries • Apple Picking • Greenport
A modern living room with a grey sofa, round coffee table, and a white fireplace.

16. 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 €2,873
includes taxes & fees
25 Oct - 26 Oct
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
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 €840
includes taxes & fees
30 Oct - 31 Oct
Immaculate Waterfront 2 bedroom!
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

18. 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 €1,378
includes taxes & fees
30 Oct - 31 Oct
Cozy Hamptons Escape 3BR Minutes From Beach!
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

Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

10/10 Excellent
"Great place, to stay and make extra money"
Alejandro 2-night trip
Posted 6 hours ago
Jake's 58 Casino Hotel - Adult Only

Find out more about Wading River

Wading River Holiday Homes information

Number of reviews
233
Accommodation
527 Holiday Homes
Lowest Price
€301
Highest Price
€2,873