Upton Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Upton holiday rentals

A room with a closed door, a potted plant, a small table with a sign, and a wall with a decorative sign.

1. Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.4 out of 10, Exceptional, (8 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is AU$349
includes taxes & fees
8 Nov - 9 Nov
Cozy king suite with kitchen and dining area.
A garden with a small waterfall, rocks, and statues.

2. Peaceful 3BR Garden Cottage Long Island Escape

Peaceful 3BR Garden Cottage Long Island Escape
Coram
10.0 out of 10, Exceptional, (1 review)
"Excellent host and peaceful getaway. I highly recommend!"
United States
Greg M.
The price is AU$644
includes taxes & fees
8 Nov - 9 Nov
Peaceful 3BR Garden Cottage Long Island Escape
A living room with a sofa, a coffee table, a TV mounted on the wall, and a window with a view of houses outside.

3. Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (29 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is AU$753
includes taxes & fees
8 Nov - 9 Nov
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
A modern kitchen with a stainless steel refrigerator, a large island with bar stools, and pendant lighting.

4. Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
9.8 out of 10, Exceptional, (7 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is AU$759
includes taxes & fees
7 Nov - 8 Nov
Modern Vacation home. Close to The Hamptons
Property grounds

5. Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping
Rocky Point
7.2 out of 10, Good, (35 reviews)
"Place was perfect for our 2 day stay. In town for family event. Was well stocked with kitchen items and bathroom. Outside area was relaxing. Quaint little place. Host communicated well and everything was as expected. Thank you"
United States
Kelly W.
The price is AU$372
includes taxes & fees
8 Nov - 9 Nov
Walk to Beach 2BR Near Dining & Shopping
A hot tub with two chairs, a pergola, and a wooden deck.

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

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (34 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is AU$2,165
includes taxes & fees
1 Dec - 2 Dec
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
A spacious living area with a fireplace, a wooden staircase, and large windows.

7. Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons
Calverton
8.2 out of 10, Very good, (12 reviews)
"Very responsive host and a beautiful house."
United States
Robin M.
The price is AU$896
includes taxes & fees
10 Nov - 11 Nov
Cozy beach hose minutes from Hamptons
A dining area with a table set for four, large windows, and a ceiling fan.

8. 3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (24 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is AU$835
includes taxes & fees
10 Nov - 11 Nov
3 Story Beach Waterview, 3 KING bed, golf putting green!
A backyard with a swimming pool, outdoor furniture, and a house with solar panels.

9. Near the Hamptons - Private Pool, Jacuzzi Retreat

Near the Hamptons - Private Pool, Jacuzzi Retreat
Calverton
6.0 out of 10, (2 reviews)
"Upon arrival, there was a notice of non payment of almost 4000 from the electric company on the door so I was concerned I would lose electric. The grounds seemedover grown and unkept. There was no TV, no hot water in the kitchen with a brokenhot water knob which would have needed a wrench. Although it had in room air conditioners vented outside, they were taped in place with open air coming inside. One of the open areas actually had live tree vines coming inside which I pulled out. There was...
United States
Theresa M.
The price is AU$1,942
includes taxes & fees
7 Nov - 8 Nov
Near the Hamptons - Private Pool, Jacuzzi Retreat
A compact kitchen with dark cabinets, stainless appliances, and a tiled floor.

10. Private 1 bedroom apt in a quiet neighborhood, close to all!

Private 1 bedroom apt in a quiet neighborhood, close to all!
Centereach
9.6 out of 10, Exceptional, (30 reviews)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is AU$347
includes taxes & fees
9 Nov - 10 Nov
Private 1 bedroom apt in a quiet neighborhood, close to all!
A living room with a brown sofa, a glass coffee table with decorative items, and a kitchen in the background with wooden cabinets and a black refrigerator.

11. Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
8.2 out of 10, Very good, (12 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is AU$458
includes taxes & fees
9 Nov - 10 Nov
Spacious one Bedroom Apt with private entrance
A spacious living area with a stone fireplace, marble flooring, and a staircase leading to another room.

12. Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC
Setauket- East Setauket
2.0 out of 10, (1 review)
"While we received multiple confirmations of our reservation, including the morning we were to check in, the property manager never sent us check in instructions, even after we emailed asking for them. Then, after spending over an hour with multiple calls to VRBO customer service, who also couldn’t get ahold of the property manager, we arrived at the location. There was a 4ft high, 10ft wide heap of garbage in the front yard and looking in through the windows it was apparent the house was under...
United States
Lisa F.
The price is AU$1,663
includes taxes & fees
7 Nov - 8 Nov
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC
A bedroom with a bed, a bedside lamp, a TV, and a door leading to another room.

13. Cozy 1-bedroom apartment in charming Centereach with AC

Cozy 1-bedroom apartment in charming Centereach with AC
Centereach
The price is AU$314
includes taxes & fees
10 Nov - 11 Nov
Cozy 1-bedroom apartment in charming Centereach with AC
A dining area with a wooden table, chairs, and a decorative wall with a cityscape picture.

14. Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,

Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
Flanders
10.0 out of 10, Exceptional, (6 reviews)
"This was a great property. Very convenient to where we like to visit. It really had everything we needed for a great weeks stay."
United States
Sherri K.
The price is AU$439
includes taxes & fees
11 Nov - 12 Nov
Nicely Furnished apartment; Ideal for Travelling nurses, Resident doctors, etc,
A modern living room with a grey sofa, round coffee table, and a white fireplace.

15. 5 Bedrooms! 4 Min to the Beach! HEATED POOL!

5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Westhampton Beach
10.0 out of 10, Exceptional, (6 reviews)
"awesome house and awesome host"
United States
Matthew M.
The price is AU$3,611
includes taxes & fees
7 Nov - 8 Nov
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
A two-story building with a prominent sign reading 'Ivy On Main' indicating a restaurant and bar.

16. Prime location, walk to all, cozy cottage Westhampton Beach

Prime location, walk to all, cozy cottage Westhampton Beach
Westhampton Beach
10.0 out of 10, Exceptional, (4 reviews)
"Property was in easy walking distance from the village which made morning coffee runs a breeze. Very clean accommodations and large back yard."
United States
Matt S.
The price is AU$816
includes taxes & fees
10 Nov - 11 Nov
Prime location, walk to all, cozy cottage Westhampton Beach
A hot tub with a checkered roof structure and surrounding greenery.

17. Jacuzzi year-round - Villa Luz Private Home

Jacuzzi year-round - Villa Luz Private Home
Hampon Bays
9.6 out of 10, Exceptional, (27 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is AU$1,611
includes taxes & fees
7 Nov - 8 Nov
Jacuzzi year-round - Villa Luz Private Home
A wooden deck with a white railing, a stone pathway, and a white fence in the background.

18. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is AU$454
includes taxes & fees
10 Nov - 11 Nov
Spacious 3BR Family Home Near Everything
A covered outdoor seating area with a white door, a 'No Smoking' sign, and string lights.

19. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (10 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is AU$497
includes taxes & fees
25 Nov - 26 Nov
The Royal Suite - Ronkonkoma
A hallway with a white door, a window with a decorative glass design, and a potted plant on a shelf.

20. Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras

Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras
Ronkonkoma
3.0 out of 10, (2 reviews)
"My sister got to the property before me and there were extra guests the owner of the property got in contact with me to let me know what was happening and told me to get everyone out or my stay would be terminated I got to the house and mad everyone leave . There was only 2 people in the house and my 2 year old son and he asked us to leave after he told me if I got everyone out I could stay. It was 1 am and I did everything he asked me to do. "
United States
Mitania L.
The price is AU$1,136
includes taxes & fees
11 Nov - 12 Nov
Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras
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

A modern kitchen with white brick backsplash, wooden cabinets, and a central island with appliances. There are two dining areas with tables and chairs.
Fairfield Inn by Marriott Medford Long Island

Fairfield Inn by Marriott Medford Long Island

Fairfield Inn by Marriott Medford Long Island
Medford

8/10 Good

Nice hotel, very clean, and good breakfast. However there is a smoking store nearby, so there may be people lingering and smoking around. Otherwise safe good hotel.
Australia
Kullanit
Reviewed October 8, 2023
Fairfield Inn by Marriott Medford Long Island

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$245 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,Beach,Fam/Pet Frly: 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.