Upton holiday rentals

We found 289 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Upton to find one that's perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Upton

Showing deals for:1 Jan - 8 Jan

Room
Pool
Pool
Exterior detail
Excellent
(36 reviews)

The Jahmtons Guest Room

Ridge

8% off
AU$1,451
for 7 nights, 1 room
AU$207 per night
includes taxes & fees
The Jahmtons Guest Room
Living area
Dining
Private kitchen
Interior
Exceptional
(6 reviews)

Shirley Bayfront Getaway – Kayak, Swim & Relax

Shirley

8% off
AU$9,450
for 7 nights, 1 home
AU$1,350 per night
includes taxes & fees
Shirley Bayfront Getaway – Kayak, Swim & Relax
Pool
Terrace/patio
Room
Exterior
Exceptional
(33 reviews)

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Mastic

15% off
AU$9,401
for 7 nights, 1 home
AU$1,343 per night
includes taxes & fees
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Pool
Exterior
Dining
Living area
Exceptional
(40 reviews)

11-Bedroom Mansion with a Seasonal Outdoor Pool open now plus 10.5 bathrooms

Eastport

8% off
AU$19,488
for 7 nights, 1 home
AU$2,784 per night
includes taxes & fees
11-Bedroom Mansion with a Seasonal Outdoor Pool open now plus 10.5 bathrooms
Room
Property grounds
Interior
Private kitchen
Very good
(34 reviews)

Waterfront Home With Recreational Dock! Great For Rafting, And Close To Beaches

Mastic Beach

8% off
AU$3,664
for 7 nights, 1 home
AU$523 per night
includes taxes & fees
Waterfront Home With Recreational Dock! Great For Rafting, And Close To Beaches
Door to outside, Like the flowers?
view as you walk into sunroom
Nice place for Breakfast in the sunroom
lower bedroom with walk in closet and king size tempurpedic bed
Exceptional
(60 reviews)

1856 Trading House w/ walk to water

Mount Sinai

12% off
AU$2,062
for 7 nights, 1 apartment
AU$295 per night
includes taxes & fees
1856 Trading House w/ walk to water
Pool
Exterior
Terrace/patio
Living area
Exceptional
(36 reviews)

40-Foot Pool Retreat Near the Hamptons — Easy NYC Access, Total Relaxation

Center Moriches

12% off
AU$5,466
for 7 nights, 1 home
AU$781 per night
includes taxes & fees
40-Foot Pool Retreat Near the Hamptons — Easy NYC Access, Total Relaxation
Terrace/patio
Living area
Private kitchen
Dining
Excellent
(27 reviews)

Relaxing Cottage -- Walk to private Beach!

Calverton

7% off
AU$3,293
for 7 nights, 1 cottage
AU$470 per night
includes taxes & fees
Relaxing Cottage -- Walk to private Beach!
Interior
Exterior detail
Interior
Private kitchen
Exceptional
(15 reviews)

Farm and Wine Lovers’ Cottage Near the Hamptons

East Moriches

7% off
AU$4,976
for 7 nights, 1 home
AU$711 per night
includes taxes & fees
Farm and Wine Lovers’ Cottage Near the Hamptons
Interior
Exterior detail
Dining
Living area
Exceptional
(14 reviews)

House of Peace

Mastic

11% off
AU$3,811
for 7 nights, 1 home
AU$544 per night
includes taxes & fees
House of Peace
Interior
Room
Terrace/patio
Exterior detail
Exceptional
(6 reviews)

South Shore Studio in Mastic

Mastic

8% off
AU$1,572
for 7 nights, 1 apartment
AU$225 per night
includes taxes & fees
South Shore Studio in Mastic
Living area
Marina
Living area
Terrace/patio
Exceptional
(12 reviews)

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Mastic Beach

12% off
AU$3,429
for 7 nights, 1 home
AU$490 per night
includes taxes & fees
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Interior
Interior
Interior
Room
Exceptional
(33 reviews)

1856 Trading House close to water

Mount Sinai

12% off
AU$2,413
for 7 nights, 1 apartment
AU$345 per night
includes taxes & fees
1856 Trading House close to water
Room
Living area
Pool
Property grounds
Exceptional
(5 reviews)

Hampton Retreat near the Beach

Remsenburg

16% off
AU$4,240
for 7 nights, 1 apartment
AU$606 per night
includes taxes & fees
Hampton Retreat near the Beach

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Upton getaway

Learn about the unique charm of Upton with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Upton

Are you searching for things to do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Upton a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Swan Lake Golf Club (4.7 mi / 7.6 km)
  • Long Island Game Farm (4.9 mi / 7.9 km)
  • Splish Splash Water Park (8.6 mi / 13.8 km)
  • Safari Adventure (11 mi / 17.7 km)
  • Paumanok Vineyards (15.4 mi / 24.8 km)
  • Jamesport Vineyards (15.7 mi / 25.3 km)

Exploring the natural landscape of Upton

Whether you're an active traveller or just want to take in the scenery, Upton is a great place to get out in nature. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Wading River Landing (6.9 mi / 11.2 km)
  • Smith Point County Park (8.9 mi / 14.3 km)
  • Shorefront Park (10.6 mi / 17 km)
  • Fire Island National Seashore (10.6 mi / 17.1 km)
  • Lake Ronkonkoma (12.9 mi / 20.8 km)
  • Avalon Park and Preserve (14.5 mi / 23.3 km)

Transport to and around Upton

Book a flight to Shirley, NY (WSH-Brookhaven Calabro), the closest airport, located 2.9 mi (4.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Westhampton, NY (FOK-Francis S. Gabreski), which is 12.6 mi (20.2 km) away.

Frequently asked questions

What is the best area to stay in Upton when booking a holiday rental?
When considering a holiday rental in Upton, New York, the surrounding areas of Brookhaven and Riverhead stand out as excellent choices. Brookhaven offers a charming suburban atmosphere with a range of properties available, making it ideal for families and those looking for a quieter retreat. The nearby Fire Island National Seashore is a top attraction, offering stunning beaches and nature trails great for outdoor enthusiasts.On the other hand, Riverhead is known for its vibrant setting and is home to the popular Long Island Aquarium, which is a fantastic spot for both adults and children. The area boasts a variety of rental options, from cozy cottages to larger homes, suiting different preferences and group sizes. Additionally, Riverhead's proximity to the North Fork wineries makes it a delightful option for those interested in exploring local vineyards and enjoying tastings.Both areas provide easy access to major highways, allowing for convenient day trips to the beautiful coastal areas or other attractions on Long Island.
Are all fees included in the Upton holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Upton holiday homes with parking?
Stayz offers a wide selection of holiday homes in Upton with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Upton holiday homes?
You can find great discounts on holiday homes in Upton on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Upton holiday home booking on Stayz?
To find Upton holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Upton?
A long-stay holiday home in Upton is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Upton holiday home?
Book your Upton holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Upton?
Prices for holiday homes in Upton vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Upton to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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