A small boat with a canopy anchored near a dock.

Westhampton Beach Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Westhampton Beach vacation homes

Roger’s Beach

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

Prime location, walk to all, cozy cottage WHB
Westhampton Beach
10.0 out of 10, Exceptional, (4 reviews)
"Property was in easy walking distance from the village which made morning coffee runs a breeze. Very clean accommodations and large back yard."
United States
Matt S.
The price is CA $568
CA $1,049 total
includes taxes & fees
Oct 21 - Oct 22
Prime location, walk to all, cozy cottage WHB
A modern living room with a grey sofa, round coffee table, and a white fireplace.

2. 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 CA $2,379
CA $3,929 total
includes taxes & fees
Oct 18 - Oct 19
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
A landscaped garden with a tree in a rectangular planter, surrounded by trimmed hedges and a wooden fence in the background.

3. 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 CA $159
CA $2,382 total
includes taxes & fees
Oct 28 - Oct 29
Jacuzzi year-round - Villa Luz Private Home
A modern building with large windows overlooking a beach.

4. Beachfront Jacuzzi All Year - Black Swan Home

Beachfront Jacuzzi All Year - Black Swan Home
Hampton Bays
9.4 out of 10, Exceptional, (21 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 CA $125
CA $1,632 total
includes taxes & fees
Oct 18 - Oct 19
Beachfront Jacuzzi All Year - Black Swan Home
A modern kitchen with a central island, white cabinetry, and a dining area with a table set for two.

5. 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 CA $383
CA $816 total
includes taxes & fees
Oct 18 - Oct 19
Immaculate Waterfront 2 bedroom!
A dining area with a table set for four, large windows, and a ceiling fan.

6. 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 CA $254
CA $885 total
includes taxes & fees
Nov 3 - Nov 4
3 Story Beach Waterview, 3 KING bed, golf putting green!
A spacious living area with a fireplace, a wooden staircase, and large windows.

7. 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 CA $471
CA $894 total
includes taxes & fees
Oct 21 - Oct 22
Cozy beach hose minutes from Hamptons
A room with a large window, a wooden bookshelf, a stone wall, and a white sofa.

8. Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Southampton
9.2 out of 10, Wonderful, (11 reviews)
"Great house with lots of space. Perfect location! The host is extremely accommodating. Definitely recommend!"
United States
Justin
The price is CA $270
CA $890 total
includes taxes & fees
Oct 25 - Oct 26
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
A swimming pool with a white deck, surrounded by lush greenery and a swan inflatable float.

9. 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)
"The house was great. Pool was beautiful and everything was a 10 minute drive! Great place to relax"
United States
Judith M.
The price is CA $639
CA $1,372 total
includes taxes & fees
Oct 26 - Oct 27
Elegant 5-Bedroom Hamptons Home with Private Pool
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, (34 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is CA $569
CA $2,043 total
includes taxes & fees
Oct 22 - Oct 23
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
A living room with a sofa, armchairs, a coffee table, and a rug.

11. 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 CA $259
CA $697 total
includes taxes & fees
Nov 3 - Nov 4
Peaceful 3BR Garden Cottage Long Island Escape
A modern kitchen with white cabinets, stainless steel appliances, a tiled backsplash, and a view to the outside.

12. Tranquil Stay

Tranquil Stay
Shirley
8.2 out of 10, Very good, (12 reviews)
"Great stay! "
United States
Emily S.
The price is CA $607
CA $1,042 total
includes taxes & fees
Oct 18 - Oct 19
Tranquil Stay
A modern kitchen with white cabinets, a dining area with a round table, and a living area with a sofa and decorative pillows.

13. 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 CA $1,703
CA $2,218 total
includes taxes & fees
Oct 22 - Oct 23
Cozy Hamptons Escape 3BR Minutes From Beach!
A modern kitchen with a stainless steel refrigerator, a large island with bar stools, and pendant lighting.

14. Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
9.8 out of 10, Exceptional, (7 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is CA $459
CA $877 total
includes taxes & fees
Oct 18 - Oct 19
Modern Vacation home. Close to The Hamptons
A living room with a sofa, a coffee table, a TV mounted on the wall, and a window with a view of houses outside.

15. 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, (29 reviews)
The price is CA $402
CA $803 total
includes taxes & fees
Oct 18 - Oct 19
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
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 CA $724
CA $1,746 total
includes taxes & fees
Oct 24 - Oct 25
North Fork Fall Escape—Vineyards, Apple Picking & Greenport
A spacious living room with a grey sectional sofa, a round coffee table, and a white armchair.

17. Minutes from the beach, brand new 4 bedroom

Minutes from the beach, brand new 4 bedroom
Southampton
10.0 out of 10, Exceptional, (6 reviews)
"perfect for families"
United States
Okito H.
The price is CA $639
CA $1,553 total
includes taxes & fees
Oct 18 - Oct 19
Minutes from the beach, brand new 4 bedroom
A backyard with a swimming pool, outdoor furniture, and a house with solar panels.

18. Near the Hamptons - Private Pool, Jacuzzi Retreat

Near the Hamptons - Private Pool, Jacuzzi Retreat
Calverton
6.0 out of 10, (1 review)
The price is CA $1,271
CA $2,109 total
includes taxes & fees
Oct 18 - Oct 19
Near the Hamptons - Private Pool, Jacuzzi Retreat
A modern two-story house with a swimming pool, a covered deck, and a well-maintained lawn.

19. Amazing Southampton Home with Private Heated Pool

Amazing Southampton Home with Private Heated Pool
Southampton
9.0 out of 10, Wonderful, (2 reviews)
"Very cozy house in a great location!"
United States
Serina R.
The price is CA $815
CA $1,792 total
includes taxes & fees
Oct 20 - Oct 21
Amazing Southampton Home with Private Heated Pool
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 Westhampton Beach Hotel Reviews

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"Inn is in a rural areas, along scenic country nestled in nature-immersed Riverhead town.Close to Riverheads amazing stores and popular eatery s They offer a more personal, relaxed atmosphere, often featuring a cozy bed rather than a corporate polish.. Great for a short business trip or as a overnite . Unique Inn atmosphere."
Elizabeth 2-night trip
Posted 2 hours ago
Greenview Inn Riverhead

Find out more about Westhampton Beach

Westhampton Beach Vacation Homes information

Number of reviews
232
Accommodation
805 Vacation Homes
Lowest Price
CA $697
Highest Price
CA $3,929

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