Upton holiday homes

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

Exterior
Bay facing side of house
Pool
Custom kitchen
Exceptional
(17 reviews)

Waterfront house next to Bellport golf course

Patchogue

8% off
NZ$8,555
for 7 nights, 1 home
NZ$1,222 per night
includes taxes & fees
Waterfront house next to Bellport golf course
Terrace/patio
Exterior
Interior
Living area
Exceptional
(33 reviews)

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

Center Moriches

12% off
NZ$6,096
for 7 nights, 1 home
NZ$871 per night
includes taxes & fees
40-Foot Pool Retreat Near the Hamptons — Easy NYC Access, Total Relaxation
Interior
Dining
Living area
Living area
Exceptional
(5 reviews)

Shirley Bayfront Getaway – Kayak, Swim & Relax

Shirley

8% off
NZ$10,597
for 7 nights, 1 home
NZ$1,514 per night
includes taxes & fees
Shirley Bayfront Getaway – Kayak, Swim & Relax
Living area
Property grounds
Pool
Dining
Excellent
(34 reviews)

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

Medford

6% off
NZ$2,411
for 7 nights, 1 home
NZ$344 per night
includes taxes & fees
Covenient Wine Country, Hamptons, Fire Island Ferry & Factory Outlet/Baseball H
Dining
Outdoor dining
Living area
Private kitchen
Exceptional
(29 reviews)

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

Mastic Beach

9% off
NZ$5,388
for 7 nights, 1 home
NZ$770 per night
includes taxes & fees
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
Interior
Property grounds
Private kitchen
Interior
Very good
(34 reviews)

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

Mastic Beach

8% off
NZ$4,389
for 7 nights, 1 home
NZ$627 per night
includes taxes & fees
Waterfront Home With Recreational Dock! Great For Rafting, And Close To Beaches
Living area
Exterior
Room
Private kitchen
Exceptional
(21 reviews)

Beautiful Private Studio Apartment!

Ridge

7% off
NZ$1,959
for 7 nights, 1 apartment
NZ$280 per night
includes taxes & fees
Beautiful Private Studio Apartment!
Dining
Exterior detail
Living area
Interior
Exceptional
(12 reviews)

House of Peace

Mastic

11% off
NZ$4,568
for 7 nights, 1 home
NZ$653 per night
includes taxes & fees
House of Peace
Exterior detail
Pool
Pool
Room
Excellent
(36 reviews)

The Jahmtons Guest Room

Ridge

8% off
NZ$1,739
for 7 nights, 1 room
NZ$248 per night
includes taxes & fees
The Jahmtons Guest Room
Dining
Interior
Pool
Private kitchen
Exceptional
(25 reviews)

Cedargate the East End's 1830's Seaside Farmhouse

East Moriches

8% off
NZ$8,381
for 7 nights, 1 home
NZ$1,197 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
NZ$1,884
for 7 nights, 1 apartment
NZ$269 per night
includes taxes & fees
South Shore Studio in Mastic
Living area
Exterior
Outdoor dining
Private kitchen
Exceptional
(20 reviews)

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

Ridge

7% off
NZ$2,390
for 7 nights, 1 apartment
NZ$341 per night
includes taxes & fees
Comfy, private one Bedroom Apartment with full kitchen, living room, full bath.
This is a shared patio space outside
view as you walk into sunroom
lower bedroom with walk in closet and king size tempurpedic bed
Door to outside, Like the flowers?
Exceptional
(59 reviews)

1856 Trading House w/ walk to water

Mount Sinai

12% off
NZ$3,628
for 7 nights, 1 apartment
NZ$518 per night
includes taxes & fees
1856 Trading House w/ walk to water
Dining
Living area
Terrace/patio
Private kitchen
Excellent
(27 reviews)

Relaxing Cottage -- Walk to private Beach!

Calverton

7% off
NZ$3,947
for 7 nights, 1 cottage
NZ$564 per night
includes taxes & fees
Relaxing Cottage -- Walk to private Beach!
Exterior
Marina
Terrace/patio
Living area
Exceptional
(9 reviews)

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

Mastic Beach

8% off
NZ$4,401
for 7 nights, 1 home
NZ$629 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
NZ$2,364
for 7 nights, 1 apartment
NZ$338 per night
includes taxes & fees
Soothing 3-bedroom apartment with AC in Farmingville
Dining
Exterior
Living area
Room
Exceptional
(37 reviews)

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

Eastport

8% off
NZ$18,435
for 7 nights, 1 home
NZ$2,634 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
NZ$3,628
for 7 nights, 1 apartment
NZ$518 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

15% off
NZ$5,178
for 7 nights, 1 apartment
NZ$740 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 Bookabach. 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 Bookabach 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.

More holiday ideas