Upton Holiday Rentals

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Holiday Rentals in Upton

Apartment in Kings Park

2.0 star property
10.0 out of 10, Exceptional, (13)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is AU$272
includes taxes & fees
10 Dec - 11 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Holiday Home in Shirley

10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is AU$950
includes taxes & fees
10 Dec - 11 Dec
Modern Vacation home. Close to The Hamptons

Holiday Home in Westhampton Beach

10.0 out of 10, Exceptional, (196)
"My family and I thoroughly enjoyed our stay! The house is very spacious and the outdoor area/pool are beautiful. Check-in was a breeze and the host was very friendly and responsive to all our questions about the home as well as offering wonderful suggestions for restaurants and beaches in the area. Would definitely recommend for a family vacation!"
United States
livinann
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Apartment in Central Islip

2.0 star property
8.0 out of 10, Very good, (2)
"Apt was clean and comfortable. Beds were comfortable. Area was nice. Owner communication was good. Only drawback is the plumbing situation was not advertised in the listing. Iif you are comfortable using a bidet and not flushing paper, this apt is perfect. "
United States
Deborah R.
The price is AU$386
includes taxes & fees
10 Dec - 11 Dec
Cozy 2 bedroom retreat in long island

Holiday Home in Calverton

2.0 star property
The price is AU$939
includes taxes & fees
10 Dec - 11 Dec
4-bedroom beach house minutes from Hamptons

Cottage in Miller Place

10.0 out of 10, Exceptional, (29)
"Fantastic stay! "
United States
Michael V.
The price is AU$496
includes taxes & fees
10 Dec - 11 Dec
Cozy Country Cottage #3

Apartment in Rocky Point

6.8 out of 10, (26)
"Great location, great host, and nice rental especially for the price! Everything went smoothly and we will be returning next year."
United States
Joshua W.
The price is AU$356
includes taxes & fees
10 Dec - 11 Dec
Walk to Beach 2BR Near Dining & Shopping

Holiday Home in Bayport

10.0 out of 10, Exceptional, (89)
"A special place and love staying here in this lovely home - looking forward to our next stay!"
United States
Roxanne M.
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Holiday Home in Brentwood

9.4 out of 10, Exceptional, (36)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
The price is AU$251
includes taxes & fees
10 Dec - 11 Dec
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Apartment in Coram

9.4 out of 10, Exceptional, (6)
"Great first time doing Vrbo great experience would do again "
United States
Rodrigo M.
Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

Holiday Home in Calverton

2.0 star property
8.6 out of 10, Excellent, (8)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is AU$1,012
includes taxes & fees
10 Dec - 11 Dec
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Holiday Home in Stony Brook

2.0 star property
8.2 out of 10, Very good, (20)
"House is well located and very comfortable.We enjoyed our stay at the home."
United States
Jim D.
Beautiful historic home in Stony Brook!

Cottage in Center Moriches

10.0 out of 10, Exceptional, (110)
"Amazing stay! Everything was super clean and beautiful "
United States
Liannys P.
The price is AU$1,143
includes taxes & fees
29 Dec - 30 Dec
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Holiday Home in Eastport

9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
United States
Gina G.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Holiday Home in East Quogue

9.6 out of 10, Exceptional, (39)
"Fantastic house for the extended family ! We loved the pool , enjoyed bbq grilling and hanging out together! "
United States
Anonymous traveller
A Quiet Place in the Hamptons

Holiday Home in Brookhaven

The price is AU$1,223
includes taxes & fees
1 Jan - 2 Jan 2026
4-bedroom house in awesome Brookhaven with AC

Holiday Home in Saint James

10.0 out of 10, Exceptional, (1)
"This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home....
United States
Devin k.
The price is AU$3,242
includes taxes & fees
14 Dec - 15 Dec
The Bella Vista St James! Waterfront house with a beach dock and so much more!

Holiday Home in Islip

9.8 out of 10, Exceptional, (22)
"Great place to stay with the family. very clean and has that home away from home feeling. Highly recommend."
United States
Brian F.
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

Apartment in Ridge

9.4 out of 10, Exceptional, (9)
"Tammy was a lovely host. She provided very detailed instructions on how to get to the Vrbo, parking location, and access in advance. Vrbo was just as pictured too! "
United States
Kristyn R.
Private One Bedroom Apartment with full kitchen, living room and full bath.

Cottage in Calverton

9.4 out of 10, Exceptional, (42)
"The description and photos are accurate. The beach is close."
United States
L A.
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
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 Upton Hotel Reviews

Find out more about Upton

Everything you need to know about Upton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upton holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Upton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upton holiday rentals we have selected for you start as low as AU$251 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Upton rentals

At Expedia, we put the best Upton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Upton?

Yes, there are holiday rentals close to the most popular sights in Upton, or you can select a more secluded option if you're looking for a relaxing stay.

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

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr: This holiday home rental outside of Upton offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Upton?

Explore the area and family-friendly sights such as Long Island Game Farm, or get out into nature at a spot like Wading River Landing. In the wider area, you’ll find Brookhaven National Laboratory and Swan Lake Golf Club.

What are holiday rentals like in Upton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upton. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip.