Oyster Bay Vacation Packages

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Your Oyster Bay Vacation

When a break in the city is calling, answer it with a Oyster Bay vacation package. The neighborhood of Cove - East Side - Shippan, which is good for cycling, coastal beaches and walking, makes a wonderful base for your adventures. If your trip to Oyster Bay includes a little sightseeing, check out popular attractions like Sagamore Hill National Historic Site, Long Island University Post Campus and Cold Spring Harbor Laboratory. Whoever you're escaping with and whatever you want to spend, your dream Oyster Bay vacation is just clicks away with Expedia.

Top Oyster Bay Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Save 100% on your flight
Price was CA $1,942, price is now CA $1,265 per person
CA $1,265
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to New York (JFK)
9.4/10 Exceptional! (275 reviews)
Perfect location

Reviewed on Oct 30, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $5,537, price is now CA $3,264 per person
CA $3,264
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $4,023, price is now CA $2,374 per person
CA $2,374
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was CA $2,689, price is now CA $1,735 per person
CA $1,735
per person
Dec 19 - Dec 26
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Great!! Everything was great

Reviewed on Oct 31, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $3,739, price is now CA $2,467 per person
CA $2,467
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

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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 CA $355 per night from Nov 22 to Nov 23
CA $355
CA $457 total
Nov 22 - Nov 23
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 CA $184 per night from Nov 2 to Nov 3
CA $184
CA $254 total
Nov 2 - Nov 3
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 Oct 31, 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 CA $126 per night from Nov 3 to Nov 4
CA $126
CA $149 total
Nov 3 - Nov 4
includes taxes & fees
Highbridge Hotel
See all 2,452 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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)
Learn about the local history of Cove Neck when you take a trip to Sagamore Hill National Historic Site. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
See properties

What to do in Oyster Bay

Private Long Island Sound Sailing Experience

Private Long Island Sound Sailing Experience

CA $919
per traveller
Private Long Island Sound Sailing Experience
Captain Steve sails a Beneteau 343

Captain Steve's Sailing Experience on Long Island

CA $776
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 vacation package cost?
You'll find cheap prices from CA $1,265 on Expedia for your Oyster Bay escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Oyster Bay costs.
What are the cheapest months to go to Oyster Bay?
Plan your trip for the off-season and you're likely to find cheap Oyster Bay vacation packages. Keep in mind that school vacation periods and local events and festivals can have an impact on prices, so do a little research before booking.
How many days is enough for Oyster Bay?
For your Oyster Bay vacation, a handful of days will be enough to see the top spots. Make sure to stop by Stehli Beach — it's one of the top attractions in this destination. If you're looking for more adventure, consider basing yourself here and going on some day trips from Oyster Bay.
Is it worth booking a vacation package to Oyster Bay?
Oyster Bay offers everything you need for an amazing escape. Get your Oyster Bay vacation off to a flying start by visiting popular attractions like Theodore Roosevelt Sanctuary and Audubon Centre.
How to find the best Oyster Bay package deals?
Use Expedia's handy filters to help you find some unbeatable Oyster Bay package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Oyster Bay package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book an Oyster Bay vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays individually. Better still, you can customize your Oyster Bay trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Oyster Bay?
If you're planning a spur-of-the-moment Oyster Bay adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Oyster Bay?

  1. Pick your travel dates: The things you'd like to do in Oyster Bay and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Oyster Bay. Then, pick a property that fits your budget, whether that's a low-cost option or a swankier retreat.
  3. Decide how long to go for: Now that you're up to speed on Oyster Bay, you can work out the ideal length of your vacation. Create a draft plan and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick an Oyster Bay vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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