Upton Vacation Rentals

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Vacation 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 CA $582
CA $1,074 total
includes taxes & fees
Aug 24 - Aug 25
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

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

2.0 out of 10, (1)
"We went to check in around 5pm since check in was at 4. Luckily we were able to leave our kids with family while we went to check out the place and unload our luggage. We arrived and parked in the street like we were told and walked to the back around the whole yard on an unfinished path. We had to step over a large roof drain pipe to get to the basement door which was not very safe. We went inside turned on the lights and proceeded to check the rooms to find the floors filthy, crumbs were all...
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

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
8.0 out of 10, Very good, (2)
"A fantastic location, and would certainly stay again! The bed was a bit hard but we all like something different. "
The price is CA $684
CA $1,251 total
includes taxes & fees
Jul 28 - Jul 29
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

10.0 out of 10, Exceptional, (2)
"Everything was as pictured, and the whole place was very clean. It was a perfect stay for us, and we will come again soon!"
The price is CA $183
CA $318 total
includes taxes & fees
Aug 5 - Aug 6
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

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

10.0 out of 10, Exceptional, (184)
"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

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

10.0 out of 10, Exceptional, (82)
"Great location. Very peaceful. Great house"
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

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

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (68)
"Wonderful time in a wonderful property. Megan the property owner was so very helpful."
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

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 CA $191
CA $422 total
includes taxes & fees
Aug 6 - Aug 7
Walk to Beach 2BR Near Dining & Shopping

Waterfront & private beach Scandinavian style house near Bellport, NY

9.6 out of 10, Exceptional, (54)
"Beautiful views and a comfortable stay."
Waterfront & private beach Scandinavian style house near Bellport, NY

Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

9.8 out of 10, Exceptional, (64)
"Great location right on the beach!"
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

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

9.8 out of 10, Exceptional, (19)
"This place was clean and comfortable, just what we needed."
The price is CA $385
CA $1,038 total
includes taxes & fees
Aug 13 - Aug 14
3 Story Beach Waterview, 3 KING bed, golf putting green!

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

10.0 out of 10, Exceptional, (1)
"Awesome house, very convenient to the beach and town. Beautiful yard and pool for grilling and hanging. Would love to come back again!"
Charming 4-bedroom house with salt water pool, AC and WiFi in Hampton Bays

Updated home in great location with spacious living & outdoor features

8.8 out of 10, Excellent, (58)
"Bunk beds, it was very clean and kitchen was great"
Updated home in great location with spacious living & outdoor features

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

Private completely fenced in property. Near beach

9.4 out of 10, Exceptional, (20)
"The place is in nice neighborhood and private entrance. It has all the amenities for a good staying. Definitely will stay again in the future."
Private completely fenced in property. Near beach

Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

9.0 out of 10, Wonderful, (2)
"Quiet neighborhood, easy checkin, great communication with host. Very clean apartment close to everything. 10/10 recommend. Will book again for next trip"
Serenity Haven: Cozy 2-Bedroom Home with Spacious Living & Big Backyard

Spacious Private Home Located on Palmer Vineyards in the North Fork,...

10.0 out of 10, Exceptional, (6)
"My wife’s family was visiting family and friends in Riverhead. We chose this house due to the location, pictures and layout. The house was great, exactly as shown. The owners were fabulous, communicated great and were responsive to our needs. We definitely will use the house again in the future"
Spacious Private Home Located on Palmer Vineyards in the North Fork,...

Summer getaway

9.4 out of 10, Exceptional, (11)
"Beautiful home with a beautiful pool"
Summer getaway
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

Frequently asked questions

Can I find vacation rentals in Upton?

Yes, you can find vacation rentals near top local attractions in Upton, or you can go with a more remote option if you're looking for relaxation.

What's the top vacation rental that Upton has to offer?

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC: Visitors like this Upton vacation home rental. It is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities like a dishwasher and a stovetop can make your vacation run smoothly.

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 larger area, you’ll find Brookhaven National Laboratory and Swan Lake Golf Club.

What are vacation rentals like in Upton?

Vacation rentals are private accommodations you can reserve for a couple days or more in Upton. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.