Westhampton Holiday Rentals

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Holiday Rentals in Westhampton

Pool
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
10.0 out of 10, Exceptional, (5)
"We loved our stay here! The hosts were very helpful and communicative leading up to and during our short stay. The house was perfect for our family - the pool area is fantastic and being able to grill food at the outdoor kitchen is such a bonus. No back and forth to the house for snacks or drinks! We spent the evening around the fire pit and the extended deck meant that there was plenty of room for us to relax and our kids to play. We also explored the local area and nearby beaches. The property...
Delightful Southampton Retreat with Pool & Outdoor Shower Near Beach & Shopping
Sun-loungers, beach towels
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (145)
"The house and area were excellent, just need some general maintenance as this property shows a lot of wear and tear. The restaurants, beach, area, and everything else were spectacular though."
The price is NZ$1,304
per night
29 May - 30 May
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is NZ$1,585
per night
20 May - 21 May
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
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Outdoor pool, a heated pool
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (22)
"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
On the beach, sun-loungers, beach towels
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
10.0 out of 10, Exceptional, (46)
"Traveling with family and dog... private walk to the beach, stylish but simple, comfortable beds, clean and organized, responsive management... 2 bedrooms downstairs, one entire 2nd floor master bedroom / entertaining space upstairs, and an attached 'cottage' king studio that is attached to the main house."
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
Exterior
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
10.0 out of 10, Exceptional, (74)
"We had a wonderful time. Loved the house, the location, walks on the beach and watching deer pass by the home on a daily basis. The house is a little worn but many older beach homes are like this. The steps up to main entrance may be a challenge for the elderly or anyone mobility limited. The dishwasher needs to be upgraded. A few minor issues when we first arrived were readily taken care of by the owner who responded quickly."
Oceanfront Home, Views from Each Room, Spectacular Sunrises and Sunsets
Fridge, microwave, oven, stovetop
Recently renovated private 2.1 acre gated home with heated pool and tennis court
10.0 out of 10, Exceptional, (11)
"This beautiful home was a great vacation home for our entire family! The house was impeccably clean with a ton of amenities, everything we wanted or needed was provided. The basketball/tennis court provided hours of entertainment for our family and the swimming pool made for a great leisurely morning or afternoon of swimming and relaxing poolside. Julie was a very attentive host and responded to our text messages for suggestions on Gurney's Seawater Spa, Vegan restaurants and more. We had a...
Recently renovated private 2.1 acre gated home with heated pool and tennis court
Fridge, microwave, oven, stovetop
Fabulous Waterfront Property in the Heart of Wine Country
10.0 out of 10, Exceptional, (153)
"Lovely home! Beautiful view! House has everything you need."
Fabulous Waterfront Property in the Heart of Wine Country
Beach nearby, sun-loungers, beach towels
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
10.0 out of 10, Exceptional, (7)
"The house was amazing, the location was perfect I could see the ocean from the living room. The only issues were the flooded roads and a few lights with dead bulbs but the flooding is understandable since its so close to the ocean. Overall we had a great time and would definitely come back."
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
Fridge, microwave, oven, stovetop
Southampton Luxury. Walk to beach, kayaks on lake. Park-like grounds.
10.0 out of 10, Exceptional, (22)
"We had a last minute corporate retreat at this lovely Hamptons Home. In time to see the beautiful fall foliage starting, there is a nice partial view of the lake from the master bedroom balcony. Our large group was easily accommodated by the spacious rooms where each person had their own comfortable bed. The large living room with 4 couches made it easy to have our meetings in this open space. A few of us went to the beach, wine tasting and pumpkin picking all within a few minutes of the house...
Southampton Luxury. Walk to beach, kayaks on lake. Park-like grounds.
Beach towels
⭐️Modern Farmhouse Long Island Wine Country🍷
10.0 out of 10, Exceptional, (13)
"We attended a family event and were looking for a home that could accommodate our family and this home fit the bill perfectly. It is in a lovely setting with all the charm and comfort you can expect. The home is updated with modern amenities and is well appointed. We really enjoyed the quiet setting, as well as easy and short drive to access shopping, dining, and more."
⭐️Modern Farmhouse Long Island Wine Country🍷
Property grounds
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
10.0 out of 10, Exceptional, (4)
The price is NZ$5,084
per night
19 May - 20 May
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...
Smart TV, fireplace, books, printers
Spectacular Beachfront Contemporary ~ Wine Country
10.0 out of 10, Exceptional, (151)
"Lovely home, right on the bay, super clean, very well , wonderful owner."
Spectacular Beachfront Contemporary ~ Wine Country
On the beach
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
9.8 out of 10, Exceptional, (49)
"Couldn't say enough positive's about this stay. The owner was very responsive from before it was even booked all the way through the stay and after. The house has a gorgeous view and it's cozy for a nice weekend away. We will definitely be back."
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
Pool
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub
9.6 out of 10, Exceptional, (82)
"Pictures don’t do justice the house is bigger in person. Everyone was able to have their own bed and private space. Lot of land"
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Outdoor pool, a heated pool
Summer getaway
9.6 out of 10, Exceptional, (5)
"We had a great stay at the house! It was much larger than we even expected and came outfitted with everything you could need for a weekend away in July. Our host was super communicative and flexible. The pool is perfect and the location is ideal for a comprehensive weekend away in the Hamptons. We will be back- thank you again!"
Summer getaway
Interior
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
9.4 out of 10, Exceptional, (11)
"The house and property were very nice but we expected there to be more beds"
The price is NZ$1,679
per night
19 May - 20 May
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Pool
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
9.4 out of 10, Exceptional, (60)
"The house was simply wonderful. It was clean and very roomy. There are many rooms in this house. The yard is to die for. We were so happy that we chose this place. The owner is wonderful and she was very easy to work with."
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
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See all available properties in Westhampton
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.

Other types of properties in Westhampton you may be interested in

Property amenity
Residence Inn by Marriott New York Long Island East End
3.0 star property
9.2 out of 10, Wonderful, (768)
"Great hotel"
The price is NZ$270
per night
21 May - 22 May
Residence Inn by Marriott New York Long Island East End
Lobby
Holiday Inn Long Island-Islip Arpt East, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (431)
"Clean "
The price is NZ$195
per night
27 May - 28 May
Holiday Inn Long Island-Islip Arpt East, an IHG Hotel
Gazebo
Hampton Inn Long Island-Brookhaven
2.5 star property
8.6 out of 10, Excellent, (1004)
"Went back to the hotel after I did not feel safe in the next hotel I had to drive to. This is a good-value, safe and clean hotel"
The price is NZ$205
per night
27 May - 28 May
Hampton Inn Long Island-Brookhaven
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Westhampton holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Westhampton. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Westhampton. Seeing all the best attractions is bound to make you fall in love with Westhampton. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Westhampton short-term rentals, that won’t be hard to do.

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?

Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres : This holiday home rental outside of Westhampton is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Westhampton?

Choose from 50 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 Out East Family Fun, 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.

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