Oyster Bay Vacation Rentals

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Vacation Rentals in Oyster Bay

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich CT

$216 nightly

$245 total

Dec 9 - Dec 10

Total with taxes and fees

With a stay at this vacation home in Greenwich, you'll be within a 15-minute drive of E. Gaynor Brennan Golf Course and Yale New Haven Health Long Ridge Medical Center.

Kitchen

Free WiFi

Charming Studio with WiFi, AC in delightful Uniondale

Uniondale NY

$159 nightly

$177 total

Jan 8 - Jan 9, 2026

Total with taxes and fees

With a stay at this vacation home in Uniondale, you'll be within a 15-minute drive of Roosevelt Field Mall and UBS Arena.

Kitchen

Air conditioning

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor NY

$411 nightly

$470 total

Dec 9 - Dec 10

Total with taxes and fees

A stay at this vacation home places you in the heart of Cold Spring Harbor, within a 15-minute walk of Cold Spring Harbor State Park and Cold Spring Harbor Whaling Museum and Education Center.

Kitchen

Washer

Westport Gem - walk to shops, dining, town center, pet-friendly

Westport CT

Located in Westport, this vacation home is within a 5-minute drive of Levitt Pavilion and Westport Country Playhouse.

Kitchen

Washer

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

New Rochelle NY

With a stay at this vacation home, you'll be centrally located in New Rochelle, within a 10-minute drive of NewYork-Presbyterian - Westchester Hospital and Iona College.

Kitchen

Free WiFi

Spacious 4-bedroom house in charming Rye with AC

Rye NY

$2,499 nightly

$2,499 total

Dec 9 - Dec 10

Total with taxes and fees

Located in Rye, Spacious 4-bedroom house in charming Rye with AC is a 5-minute drive from Rye Playland and 6 minutes from Emelin Theatre.

Pet friendly

Air conditioning

Marvelous 5-bedroom house with AC in Yonkers

Yonkers NY

With a stay at this vacation home in Yonkers (Bryn Mawr), you'll be within a 15-minute drive of Yankee Stadium and NewYork-Presbyterian - Westchester Hospital.

Washer

Dryer

LUXURY BAY SHORE HOME

17 Mowbray Ave Bay Shore NY

With a stay at this vacation home in Bay Shore, you'll be within a 5-minute walk of Gilgo State Park and South Shore University Hospital.

Pet friendly

Parking included

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

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Northport NY

When you a stay at this vacation home in Northport, you'll be on the beach, within a 5-minute walk of Cow Harbor Park and Northport Village Park.

Hot Tub

Kitchen

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Syosset NY

With a stay at this vacation home, you'll be centrally located in Jericho, within a 10-minute drive of Roosevelt Field Mall and Broadway Mall.

Pool

Hot Tub

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

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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.