Westhampton Holiday Rentals

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Holiday Rentals in Westhampton

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

9.8 out of 10, Exceptional, (32)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Smart TV, fireplace, video games, stereo

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

10.0 out of 10, Exceptional, (101)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is HK$1,751
HK$4,046 total
includes taxes & fees
16 Oct - 17 Oct
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Walk to Beach 2BR Near Dining & Shopping
Property grounds

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (20)
"Stay away"
The price is HK$876
HK$2,148 total
includes taxes & fees
8 Oct - 9 Oct
Walk to Beach 2BR Near Dining & Shopping
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Fridge, microwave, oven, stovetop

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
10 Bedroom Hampton House with a regulation size Pickleball court
Pool

10 Bedroom Hampton House with a regulation size Pickleball court

10.0 out of 10, Exceptional, (32)
"Cannot say enough good things. Unique, sprawling, beautiful property with more than enough room for a large group. Endless entertainment, great pool, walking distance from a few bars and restaurants. Great communication and accommodation from our host. Would recommend and rent again."
10 Bedroom Hampton House with a regulation size Pickleball court
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

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

9.6 out of 10, Exceptional, (137)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Modern Vacation home. Close to The Hamptons
Fridge, microwave, oven, stovetop

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is HK$2,661
HK$4,997 total
includes taxes & fees
12 Oct - 13 Oct
Modern Vacation home. Close to The Hamptons
Cozy Country Cottage #3
Interior

Cozy Country Cottage #3

10.0 out of 10, Exceptional, (27)
"Very clean and comfortable "
The price is HK$1,167
HK$2,543 total
includes taxes & fees
23 Oct - 24 Oct
Cozy Country Cottage #3
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (191)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is HK$6,187
HK$9,933 total
includes taxes & fees
17 Oct - 18 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Oven, stovetop, dishwasher

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
8.4 out of 10, Very good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
The price is HK$3,883
HK$7,015 total
includes taxes & fees
13 Oct - 14 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Outdoor spa tub

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

9.6 out of 10, Exceptional, (23)
"This was the perfect location to enjoy the vineyards for my friend’s bachelorette party. Everyone had a comfy room and the space was very generous. Additionally the yard was massive and had ample seating. We had a great time and would definitely recommend this to all!"
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Stylish Five-Bedroom Oasis w/ Pool, Minutes from Beaches, Wineries & the...
Terrace/patio

Stylish Five-Bedroom Oasis w/ Pool, Minutes from Beaches, Wineries & the...

10.0 out of 10, Exceptional, (1)
"the house is huge and well appointed. the outdoor space with the huge handsome awning set the stage. couch outside should be replaced but it's a small complaint in the big scheme of this house. updated bathrooms and bedrooms with four twin beds in total - very flexible living. pool outstanding, very deep and beautiful setting outside. could upgrade patio loungers but again not really detrimental and kind of charming"
Stylish Five-Bedroom Oasis w/ Pool, Minutes from Beaches, Wineries & the...
Tranquil Stay
Fridge, microwave, oven, stovetop

Tranquil Stay

10.0 out of 10, Exceptional, (6)
"Great stay with family to see a couple of our son's shows at the Gateway Theatre. Thank you Andre for be a great host...!!!"
The price is HK$2,568
HK$4,659 total
includes taxes & fees
23 Oct - 24 Oct
Tranquil Stay
Beach, Pool, Wine, Shopping!
Beach nearby, beach towels

Beach, Pool, Wine, Shopping!

10.0 out of 10, Exceptional, (73)
"The check-in process and communication couldn't have been easier. The property was clean, comfortable, and had everything we needed to enjoy ourselves. Conveniently located a walkable distance from Love Lane and a short drive from wineries (which is what brought us to the area)"
Beach, Pool, Wine, Shopping!
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Terrace/patio

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

9.8 out of 10, Exceptional, (16)
"Had an amazing stay here and would definitely recommend to others!! Only issue was the heat did not work in certain areas. House and backyard / pool area was spacious and beautiful. Perfect for large groups. Would definitely stay again."
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Summer getaway
Outdoor dining

Summer getaway

9.0 out of 10, Wonderful, (14)
"Perfect location for a family holiday "
Summer getaway
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Sun-loungers, beach towels

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

9.4 out of 10, Exceptional, (41)
"I went with family for a memorial celebration for a family member who had passed away. Worked out great and enjoyed the back deck & fire pit! Also, beds were comfy and open kitchen & LR were great for entertaining! Thank you Billy:)"
The price is HK$1,044
HK$2,882 total
includes taxes & fees
15 Oct - 16 Oct
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Outdoor pool, a heated pool

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

9.4 out of 10, Exceptional, (73)
"Enjoyed our time. Thank you "
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Private beach on a fenced in property sunset views
Terrace/patio

Private beach on a fenced in property sunset views

10.0 out of 10, Exceptional, (12)
"We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay."
Private beach on a fenced in property sunset views
Luxury 8BR Villa w/ Heated Pool, Hot Tubs, Home Theater – Sleeps 16
Exterior

Luxury 8BR Villa w/ Heated Pool, Hot Tubs, Home Theater – Sleeps 16

10.0 out of 10, Exceptional, (20)
"Super clean, spacious, and plenty of sleeping space"
Luxury 8BR Villa w/ Heated Pool, Hot Tubs, Home Theater – Sleeps 16
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 Hotel Reviews

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"I was really impressed with the modern, clean room. I loved the sliding barn door..clean, white bedding & refillable soap & shampoo & conditioner. No more little plastic bottles that never hold enough to even wash one person’s hair. I also lined the separate reading lights. The gentleman checking us in was pleasant and it took a very short time. I would definitely consider another visit next time I am visiting the North Fork of Long Island."
carol 1-night trip
Posted 1 day ago
Greenview Inn Riverhead

Find out more about Westhampton

Find out more about Westhampton

Search for holiday rentals in Westhampton on Expedia! You can easily find your home rentals, villas, holiday apartments in Westhampton using one of the methods below:

  • View our selection of featured holiday rentals in Westhampton
  • Use the map to find apartments and other holiday homes in the Westhampton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Westhampton while they last

Look no further and take a look at our great range of rental properties in Westhampton!

Frequently asked questions

Can I find a holiday rental in Westhampton?

Yes, there are holiday rentals close to the most popular sights in Westhampton, or you can select a more secluded option if you're looking for a relaxing stay. Westhampton is known for its restaurants and shopping.

What are some of the best holiday rentals that Westhampton has to offer?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This holiday home rental outside of Westhampton offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Westhampton?

Choose from 51 Expedia holiday rentals in Westhampton for a memorable holiday.

What can I see and do in Westhampton?

While exploring the area, visit family-friendly sights like Long Island Game Farm, or get outside and enjoy nature at Moriches Bay. In the wider area, you’ll find Westhampton Beach Performing Arts Center and Suffolk Theater.

What’s a holiday rental in Westhampton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Westhampton. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family getaway.