Oyster Bay Holidays

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Oyster Bay Holiday

Our pick of the best Oyster Bay Hotel Deals

TWA Hotel at JFK Airport

TWA Hotel at JFK Airport

4 out of 5
One Idlewild Drive Jamaica NY
Fully refundableReserve now, pay when you stay
The price is NZ$581 per night from 22 Nov to 23 Nov
NZ$581
22 Nov - 23 Nov
includes taxes & fees
TWA Hotel at 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$323 per night from 2 Nov to 3 Nov
NZ$323
2 Nov - 3 Nov
includes taxes & fees
8.4/10 Very good! (2,332 reviews)
"I’ve had my eye on the hotel for a while but it’s way uptown…on my last trip to NY, though, it was the only reasonably priced place so I spent a night. Really nice, feels new, nice room, big shower, breakfast was great. It’s two blocks from the subway. Very Latino neighborhood. I’d stay there again. ..."

Reviewed on 31 Oct 2026

Radio Hotel
Highbridge Hotel

Highbridge Hotel

2 out of 5
1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
The price is NZ$190 per night from 3 Nov to 4 Nov
NZ$190
3 Nov - 4 Nov
includes taxes & fees
Highbridge Hotel
See all 2,477 properties in Oyster Bay
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.

Stay near popular Oyster Bay attractions

A large, historic house with a red brick porch and a covered front porch area.
Photo by Henry Tovmassian
Open Photo by Henry Tovmassian

Sagamore Hill National Historic Site

8.8/10 (20 reviews)
Theodore Roosevelt's grand Victorian mansion offers an intimate glimpse into the 26th president's personal life. Tour the meticulously preserved home with original furnishings and explore the surrounding natural estate.
See properties

What to do in Oyster Bay

Private Long Island Sound Sailing Experience

Private Long Island Sound Sailing Experience

NZ$1,145
per traveller
Private Long Island Sound Sailing Experience
Captain Steve sails a Beneteau 343

Captain Steve's Sailing Experience on Long Island

NZ$969
per traveller
Captain Steve's Sailing Experience on Long Island
See all activities in Oyster Bay

Frequently asked questions

How much does an Oyster Bay holiday package cost?
You'll find cheap prices on Expedia for your Oyster Bay escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your holiday to Oyster Bay costs.
What are the cheapest months to go to Oyster Bay?
Travel in the low season and you're likely to get cheap Oyster Bay holiday packages. Remember that public holidays and local events and festivals can impact prices, so do a little research before you go.
How many days is enough for Oyster Bay?
Typically, a handful of days is ideal for an Oyster Bay holiday. With a well-planned itinerary, you can check out all the popular sights like Theodore Roosevelt Memorial Park, as well as explore some hidden treasures along the way.
Is it worth booking a holiday package to Oyster Bay?
Oyster Bay is a good holiday destination with attractions like Theodore Roosevelt Sanctuary and Audubon Centre among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, an Oyster Bay holiday promises a good time for everyone.
How to find the best Oyster Bay package deals?
Begin your search for an Oyster Bay package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Oyster Bay package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oyster Bay escape off to a flying start.
Is it cheaper to book an Oyster Bay holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still get the flexibility to create a personalised Oyster Bay holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Oyster Bay?
If you're considering a spur-of-the-moment Oyster Bay adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Oyster Bay?

  1. Choose your dates: What you'd like to do in Oyster Bay and your preferred season will help you decide when to travel.
  2. Budget wisely: As well as the price of your accommodation, you should factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that could arise during your trip to Oyster Bay.
  3. Decide your trip length: Think about how long you'd like to spend discovering Oyster Bay. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your airfare and accommodation: After you've settled on your dates and duration, lock in the ideal Oyster Bay holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.