Upton Vacation Rentals

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Vacation Rentals in Upton

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!

Jamesport NY

Located in Riverhead, this vacation home is within a 15-minute walk of Terra Vite North Fork Winery & Vineyard and Jason's Vineyard.

Kitchen

Washer

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Centereach NY

With a stay at this vacation home in Centereach, you'll be within a 5-minute drive of Stony Brook University and Smithaven Mall.

Washer

Dryer

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Brentwood NY

$144 nightly

$165 total

Dec 9 - Dec 10

Total with taxes and fees

Located in Brentwood, this vacation home is within a 5-minute drive of Hauppauge Industrial Park and Nissequogue River.

Pet friendly

Free WiFi

fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

Islip NY

Located in Islip, this vacation home is within a 5-minute drive of Bethpage Ballpark and Cohalan Court Complex.

Kitchen

Washer

Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

Sound Beach NY

Located in Sound Beach, this vacation home is by the sea, a 3-minute drive from Cedar Beach and 5 minutes from Clifton H. Lee Memorial Park.

Kitchen

Washer

Drifted Inn. North Fork Escape Paradise!

Riverhead NY

When you stay at this vacation home in Riverhead, you'll be near the beach and 7 minutes by car from Hallockville Museum Farm.

Hot Tub

Kitchen

🌞 DUNE ROAD STEPS TO THE OCEAN - 4 BEDROOM HOME ⛱ 🌊

Westhampton Beach NY

With a stay at this vacation home in Westhampton Beach, you'll be on the beach, just a 2-minute walk from Moriches Bay and 6 minutes by foot from The Hamptons Beaches.

Kitchen

Washer

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

Westhampton Beach NY

Located in Westhampton Beach, this vacation home is by the sea, within a 5-minute drive of Westhampton Beach Performing Arts Center and Quogue Community Hall.

Pool

Kitchen

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches

Stony Brook NY

With a stay at this vacation home in Stony Brook, you'll be within a 10-minute drive of Stony Brook University and Stony Brook Village Center.

4-bedroom house in awesome Brookhaven with AC

Brookhaven NY

$703 nightly

$803 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

Located in Brookhaven, this vacation home is within a 5-minute drive of Gateway Playhouse and Great South Bay.

Washer

Dryer

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

Hampton Bays NY

Located in Hampton Bays, this vacation home is by the sea, within a 5-minute drive of Good Ground Park and Regal UA Hampton Bays.

Pool

Kitchen

Modern 1 bedroom apartment near Stony Brook university hospital walking distance

Stony Brook NY

With a stay at this vacation home, you'll be centrally located in Stony Brook, just a 5-minute walk from Stony Brook University and 14 minutes by foot from Long Island Museum of American Art, History, and Carriages.

Kitchen

Washer

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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.