Book Holiday Homes in Oyster Bay

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Featured Holiday Homes in Oyster Bay

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

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

Brentwood
The price is NZ$278 per night from 24 Aug to 25 Aug
NZ$278
24 Aug - 25 Aug
includes taxes & fees
Stay at this vacation home in Brentwood. Enjoy free WiFi, an in-room coffeemaker, and housekeeping. Popular attractions Brentwood State Park and Stonebridge ...
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Charming 1-bedroom house with WiFi, AC in delightful Uniondale

Charming 1-bedroom house with WiFi, AC in delightful Uniondale

Uniondale
The price is NZ$307 per night from 19 Aug to 20 Aug
NZ$307
19 Aug - 20 Aug
includes taxes & fees
Stay at this vacation home in Uniondale. Enjoy air conditioning. Popular attractions Nassau Veterans Memorial Coliseum and Roosevelt Field Mall are located ...
Charming 1-bedroom house with WiFi, AC in delightful Uniondale
Waterfront Beach House 30 Min from New York City

Waterfront Beach House 30 Min from New York City

Bellmore
Stay at this vacation home in Bellmore. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northwell Health at Jones Beach Theater and Jones ...
Waterfront Beach House 30 Min from New York City
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Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
The price is NZ$1,117 per night from 1 Sept to 2 Sept
NZ$1,117
1 Sept - 2 Sept
includes taxes & fees
Book a stay at this family-friendly vacation home in Cold Spring Harbor. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the helpful staff ...
Captain's Cottage - Cold Spring Harbor Water Views
Walkable to all in Downtown Seaford! Clean 1 bed basement unit

Walkable to all in Downtown Seaford! Clean 1 bed basement unit

Seaford
Stay at this vacation home in Seaford. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Northwell Health at Jones Beach Theater ...
Walkable to all in Downtown Seaford! Clean 1 bed basement unit
Charming 3-bedroom modern family retreat!

Charming 3-bedroom modern family retreat!

Huntington
Stay at this vacation home in Huntington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bethpage Black State Park Golf Course and Oheka ...
Charming 3-bedroom modern family retreat!
Beautiful historic home in Stony Brook!

Beautiful historic home in Stony Brook!

2 out of 5
Stony Brook
Stay at this vacation home in Stony Brook. Enjoy laundry facilities and air conditioning. Popular attractions Stony Brook Village Center and Stony Brook Grist ...
Beautiful historic home in Stony Brook!
Coastal Retreat 6 MI To Jones Beach

Coastal Retreat 6 MI To Jones Beach

Roosevelt
Stay at this vacation home in Roosevelt. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Nassau Veterans Memorial Coliseum and Roosevelt ...
Coastal Retreat 6 MI To Jones Beach
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Adorable Cottage with Water Views, Across the street from Prime & other eateries

Halesite
Stay at this vacation home in Huntington. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Heckscher Museum of Art and Chateau ...
Adorable Cottage with Water Views, Across the street from Prime & other eateries
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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.

Oyster Bay Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oyster Bay vacation homes are the perfect way for you to wing it.

Holiday houses in Oyster Bay let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oyster Bay in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oyster Bay adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oyster Bay with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oyster Bay vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oyster Bay Holiday Homes essential information

Accommodation
672 Holiday Homes
Lowest Price
NZ$245
Highest Price
NZ$1,117
Popular accommodation
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. , Charming 1-bedroom house with WiFi, AC in delightful Uniondale, Waterfront Beach House 30 Min from New York City, Captain's Cottage - Cold Spring Harbor Water Views, Walkable to all in Downtown Seaford! Clean 1 bed basement unit, Charming 3-bedroom modern family retreat!, Beautiful historic home in Stony Brook!, Coastal Retreat 6 MI To Jones Beach, Adorable Cottage with Water Views, Across the street from Prime & other eateries

Top trending hotels in Oyster Bay

Five Towns Inn - JFK Airport

Five Towns Inn - JFK Airport

2 out of 5
655 Rockaway Tpke, Lawrence, NY
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Lawrence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Five Towns Inn - JFK Airport
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave, New York, NY
Fully refundableReserve now, pay when you stay
The price is NZ$331 per night from 1 Sept to 2 Sept
NZ$331
1 Sept - 2 Sept
includes taxes & fees
Stay at this 4-star hotel in New York. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
Radio Hotel
Ly New York Hotel

Ly New York Hotel

2.5 out of 5
15-61 127th St, College Point, NY
Fully refundableReserve now, pay when you stay
The price is NZ$390 per night from 19 Aug to 20 Aug
NZ$390
19 Aug - 20 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in College Point. Enjoy free WiFi, a 24-hour front desk, and a business center. Popular attractions Citi Field and ...
Ly New York Hotel
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Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

3 out of 5
200 West Main Street, Elmsford, NY
Fully refundableReserve now, pay when you stay
The price is NZ$245 per night from 1 Sept to 2 Sept
NZ$245
1 Sept - 2 Sept
includes taxes & fees
Stay at this 3-star business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hampton Inn White Plains/Tarrytown
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See all available properties in Oyster Bay
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.