Upton Holiday Rentals

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Holiday Rentals in Upton

East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

10.0 out of 10, Exceptional, (88)
"Great property, great views and the owner was terrific in his communication and hospitality.Thank you! "
The price is NZ$1,289
includes taxes & fees
22 July - 23 July
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

The price is NZ$373
includes taxes & fees
17 July - 18 July
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

10.0 out of 10, Exceptional, (10)
"An absolute perfect home for a family looking to enjoy"
July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."
Lovely North Fork Beach Cottage (2 BR/2 bath)!

Walk to Beach 2BR Near Dining & Shopping

6.2 out of 10, (14)
"The home is cute and cozy--located close enough to attractions and restaurants but off the beaten path."
The price is NZ$519
includes taxes & fees
21 July - 22 July
Walk to Beach 2BR Near Dining & Shopping

FARM TO TABLE BREAKFAST

10.0 out of 10, Exceptional, (25)
"Margaret was the perfect hostess. The house was interesting and artistic and the breakfasts delicious. The accommodations were comfortable with everything you need plus provided!"
FARM TO TABLE BREAKFAST

Waterfront & private beach Scandinavian style house near Bellport, NY

9.6 out of 10, Exceptional, (52)
"Beautiful views and a comfortable stay."
Waterfront & private beach Scandinavian style house near Bellport, NY

Updated home in great location with spacious living & outdoor features

8.8 out of 10, Excellent, (54)
"Bunk beds, it was very clean and kitchen was great"
Updated home in great location with spacious living & outdoor features

Beautiful 3 Bedroom house

8.6 out of 10, Excellent, (11)
"Nice place "
Beautiful 3 Bedroom house

Summer getaway

9.2 out of 10, Wonderful, (10)
"Beautiful home with a beautiful pool"
Summer getaway

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (183)
"Everything was amazing, the house is beautiful and very spacious, and the host was very friendly! I would 100% stay here again! "
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

A Quiet Place in the Hamptons

9.8 out of 10, Exceptional, (36)
"Our wine club had a great time staying here! The house had everything we needed and tons of space. Special thanks to Matteo for being super responsive and accommodating!"
A Quiet Place in the Hamptons

Westhampton Beach Town and Country

9.8 out of 10, Exceptional, (35)
"Outdoor space was wonderful. The house was well stocked with supplies."
Westhampton Beach Town and Country

5 bedroom Private Family Get Away w/ Heated Pool

10.0 out of 10, Exceptional, (13)
"Wonderful place! Excellent location and facilities. Very homely and just what we needed in so many ways!"
5 bedroom Private Family Get Away w/ Heated Pool

Muwu in Wading River - secluded cabin with private beach and built in sauna

10.0 out of 10, Exceptional, (1)
Muwu in Wading River - secluded cabin with private beach and built in sauna

Charming 4-bedroom house with salt water pool, AC and WiFi in Hampton Bays

Charming 4-bedroom house with salt water pool, AC and WiFi in Hampton Bays

5 Bedrooms! 4 Min to the Beach! HEATED POOL!

10.0 out of 10, Exceptional, (1)
"Communication with the property manager was an A. Highly recommend this home! "
The price is NZ$5,373
includes taxes & fees
17 July - 18 July
5 Bedrooms! 4 Min to the Beach! HEATED POOL!

3 Story Beach Waterview, 3 KING bed, golf putting green!

9.8 out of 10, Exceptional, (18)
"This place was clean and comfortable, just what we needed."
The price is NZ$1,116
includes taxes & fees
16 July - 17 July
3 Story Beach Waterview, 3 KING bed, golf putting green!
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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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?

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms: This holiday home rental outside of Upton is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Smith Point County Park. 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.