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

Search Vacation Homes in Wading River

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Wading River vacation 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 ￥36,937
￥79,173 total
includes taxes & fees
Oct 6 - Oct 7
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
8.2 out of 10, Very good, (11 reviews)
"Very responsive host and a beautiful house."
United States
Robin M.
The price is ￥65,208
￥115,979 total
includes taxes & fees
Oct 6 - Oct 7
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 ￥28,839
￥78,213 total
includes taxes & fees
Oct 5 - Oct 6
Peaceful 3BR Garden Cottage Long Island Escape
Roger’s Beach

4. Prime location, walk to all, cozy cottage WHB

Prime location, walk to all, cozy cottage WHB
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 ￥63,140
￥113,437 total
includes taxes & fees
Oct 19 - Oct 20
Prime location, walk to all, cozy cottage WHB
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
9.8 out of 10, Exceptional, (6 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is ￥51,001
￥97,584 total
includes taxes & fees
Oct 6 - Oct 7
Modern Vacation home. Close to The Hamptons
A backyard with a swimming pool, outdoor furniture, and a house with solar panels.

6. 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 ￥141,355
￥234,900 total
includes taxes & fees
Oct 5 - Oct 6
Near the Hamptons - Private Pool, Jacuzzi Retreat
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 ￥18,184
￥54,679 total
includes taxes & fees
Oct 5 - Oct 6
The Royal Suite - Ronkonkoma
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 ￥17,679
￥264,960 total
includes taxes & fees
Oct 5 - Oct 6
Jacuzzi year-round - Villa Luz Private Home
A dining area with a table set for four, large windows, and a ceiling fan.

9. 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 ￥30,623
￥101,717 total
includes taxes & fees
Oct 27 - Oct 28
3 Story Beach Waterview, 3 KING bed, golf putting green!
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 ￥78,925
￥241,301 total
includes taxes & fees
Oct 22 - Oct 23
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
A modern kitchen with white cabinets, stainless steel appliances, a tiled backsplash, and a view to the outside.

11. Tranquil Stay

Tranquil Stay
Shirley
8.2 out of 10, Very good, (12 reviews)
"Great stay! "
United States
Emily S.
The price is ￥67,481
￥115,871 total
includes taxes & fees
Oct 5 - Oct 6
Tranquil Stay
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 ￥17,837
￥189,120 total
includes taxes & fees
Oct 6 - Oct 7
Beachfront Jacuzzi All Year - Black Swan Home
A modern living room with a grey sofa, round coffee table, and a white fireplace.

13. 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 ￥264,557
￥436,972 total
includes taxes & fees
Oct 5 - Oct 6
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
A dining area with a white table, gold chairs, and a potted plant.

14. The Bay House Patchogue Bay & Town 10 Minutes Walk

The Bay House Patchogue Bay & Town 10 Minutes Walk
Patchogue
10.0 out of 10, Exceptional, (1 review)
"Had a lovely stay at this home. Nice amenities, comfy beds, private back patio. Location was perfect for our trip."
United States
Adam B.
The Bay House Patchogue Bay & Town 10 Minutes Walk
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

15. 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 ￥42,620
￥90,715 total
includes taxes & fees
Oct 8 - Oct 9
Immaculate Waterfront 2 bedroom!
A rocky beach with clear water and a forested hillside in the background.

16. 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 ￥94,710
￥216,412 total
includes taxes & fees
Oct 24 - Oct 25
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

17. 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 ￥71,033
￥154,555 total
includes taxes & fees
Oct 5 - Oct 6
Elegant 5-Bedroom Hamptons Home with Private Pool
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.

18. 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 ￥35,516
￥46,169 total
includes taxes & fees
Nov 1 - Nov 2
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.

19. 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 ￥189,420
￥247,252 total
includes taxes & fees
Oct 5 - Oct 6
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.
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

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

10/10 Excellent
"This hotel was clean, comfy and reasonably priced. Everything worked out well virtually checking in and was perfect for our one night stay. Parking was a little nerve racking since there was no parking on the premise but the street parking worked out well reading the street signs and moving the car when necessary."
Richard 1-night trip
Posted 11 hours ago
Hampton Bays Hotel on Main

Find out more about Wading River

Wading River Vacation Homes information

Number of reviews
239
Accommodation
538 Vacation Homes
Lowest Price
￥46,169
Highest Price
￥436,972