Upton holiday rentals

We found 285 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:13 Nov - 20 Nov

Pool
Bay facing side of house
Exterior
Game room
Exceptional
(17 reviews)

Waterfront house next to Bellport golf course

Patchogue

8% off
AU$7,055
for 7 nights, 1 home
AU$1,008 per night
includes taxes & fees
Waterfront house next to Bellport golf course
Pool
Exterior
Terrace/patio
Interior
Exceptional
(33 reviews)

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

Center Moriches

12% off
AU$4,996
for 7 nights, 1 home
AU$714 per night
includes taxes & fees
40-Foot Pool Retreat Near the Hamptons — Easy NYC Access, Total Relaxation
Living area
Dining
Interior
Living area
Exceptional
(5 reviews)

Shirley Bayfront Getaway – Kayak, Swim & Relax

Shirley

8% off
AU$8,684
for 7 nights, 1 home
AU$1,241 per night
includes taxes & fees
Shirley Bayfront Getaway – Kayak, Swim & Relax
Pool
Property grounds
Living area
Exterior
Excellent
(34 reviews)

Covenient Wine Country, Hamptons, Fire Island Ferry & Factory Outlet/Baseball H

Medford

6% off
AU$2,046
for 7 nights, 1 home
AU$292 per night
includes taxes & fees
Covenient Wine Country, Hamptons, Fire Island Ferry & Factory Outlet/Baseball H
Dining
Outdoor dining
Private kitchen
Living area
Exceptional
(29 reviews)

“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath

Mastic Beach

9% off
AU$4,385
for 7 nights, 1 home
AU$626 per night
includes taxes & fees
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
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$3,643
for 7 nights, 1 home
AU$520 per night
includes taxes & fees
Waterfront Home With Recreational Dock! Great For Rafting, And Close To Beaches
Private kitchen
Exterior
Outdoor dining
Room
Exceptional
(21 reviews)

Beautiful Private Studio Apartment!

Ridge

7% off
AU$1,626
for 7 nights, 1 apartment
AU$232 per night
includes taxes & fees
Beautiful Private Studio Apartment!
Dining
Exterior detail
Interior
Exterior
Exceptional
(12 reviews)

House of Peace

Mastic

11% off
AU$3,717
for 7 nights, 1 home
AU$531 per night
includes taxes & fees
House of Peace
Room
Pool
Room
Pool
Excellent
(36 reviews)

The Jahmtons Guest Room

Ridge

8% off
AU$1,443
for 7 nights, 1 room
AU$206 per night
includes taxes & fees
The Jahmtons Guest Room
Exterior
Interior
Dining
Private kitchen
Exceptional
(25 reviews)

Cedargate the East End's 1830's Seaside Farmhouse

East Moriches

8% off
AU$6,908
for 7 nights, 1 home
AU$987 per night
includes taxes & fees
Cedargate the East End's 1830's Seaside Farmhouse
Exterior detail
Room
Private kitchen
Interior
Exceptional
(6 reviews)

South Shore Studio in Mastic

Mastic

8% off
AU$1,563
for 7 nights, 1 apartment
AU$223 per night
includes taxes & fees
South Shore Studio in Mastic
Outdoor dining
Exterior
Living area
Private kitchen
Exceptional
(20 reviews)

Comfy, private one Bedroom Apartment with full kitchen, living room, full bath.

Ridge

7% off
AU$2,029
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
Comfy, private one Bedroom Apartment with full kitchen, living room, full bath.
lower bedroom with walk in closet and king size tempurpedic bed
view as you walk into sunroom
Door to outside, Like the flowers?
This is a shared patio space outside
Exceptional
(59 reviews)

1856 Trading House w/ walk to water

Mount Sinai

12% off
AU$3,036
for 7 nights, 1 apartment
AU$434 per night
includes taxes & fees
1856 Trading House w/ walk to water
Private kitchen
Living area
Terrace/patio
Interior
Excellent
(27 reviews)

Relaxing Cottage -- Walk to private Beach!

Calverton

7% off
AU$3,274
for 7 nights, 1 cottage
AU$468 per night
includes taxes & fees
Relaxing Cottage -- Walk to private Beach!
Terrace/patio
Marina
Exterior
Living area
Exceptional
(9 reviews)

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

Mastic Beach

8% off
AU$3,655
for 7 nights, 1 home
AU$522 per night
includes taxes & fees
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Interior
Dining
Living area
Private kitchen
Very good
(5 reviews)

Soothing 3-bedroom apartment with AC in Farmingville

Farmingville

8% off
AU$2,008
for 7 nights, 1 apartment
AU$287 per night
includes taxes & fees
Soothing 3-bedroom apartment with AC in Farmingville
Room
Exterior
Living area
Pool
Exceptional
(37 reviews)

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

Eastport

8% off
AU$15,370
for 7 nights, 1 home
AU$2,196 per night
includes taxes & fees
11-Bedroom Mansion with a Seasonal Outdoor Pool open now plus 10.5 bathrooms
Room
Interior
Interior
Interior
Exceptional
(30 reviews)

1856 Trading House close to water

Mount Sinai

12% off
AU$3,036
for 7 nights, 1 apartment
AU$434 per night
includes taxes & fees
1856 Trading House close to water
Property grounds
Living area
Property grounds
Pool
Exceptional
(5 reviews)

Hampton Retreat near the Beach

Remsenburg

16% off
AU$4,216
for 7 nights, 1 apartment
AU$602 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)
  • Palmer Vineyards (15 mi / 24.1 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:

  • Cedar Beach (7.8 mi / 12.6 km)
  • Smith Point County Park (8.9 mi / 14.3 km)
  • Cupsoque Beach (10.1 mi / 16.2 km)
  • Cupsogue County Park (10.1 mi / 16.2 km)
  • Shorefront Park (10.6 mi / 17 km)
  • Fire Island National Seashore (10.6 mi / 17.1 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

How much does it cost to rent a holiday home in Upton?
The average price for a holiday home in Upton is based on several factors, such as property type, length of stay and season. Whether you're dreaming about a sprawling villa with space for the whole family or a comfy cabin just for the two of you, just enter your dates of travel to view stays with terrific value.
How much does it cost to rent a beach house in Upton?
When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Put in your Upton travel dates to view your available options on Stayz. Can't live without a private pool? Use our filters to pick the amenities and features you want.
What are the top attractions for families in Upton?
Keep your kids occupied at these popular family-friendly attractions in Upton:
  • Splish Splash Water Park
  • Long Island Game Farm
  • Boomers! Medford
How old do you have to be to rent a holiday home in Upton?
We recommend checking with the Upton holiday home you want on Stayz as age restrictions differ. However, normally it's 16, 18 or 21.
How long can I rent a holiday home in Upton for?
The amount of time you can rent an Upton holiday home for depends on each property. Simply put in your dates of travel to see available options that offer long-term stays. They feature all you need to make your extended getaway more comfortable and enjoyable, like laundries and air conditioning. Some holiday homes might also offer weekly or monthly discounted prices, so you can stick around for longer for less.

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