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.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,587, price is now CA $991 per person
CA $991
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! (4,080 reviews)
The best hotel near Times Square

Reviewed on Oct 27, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,969, price is now CA $1,234 per person
CA $1,234
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,714 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,176, price is now CA $1,383 per person
CA $1,383
per person
Dec 9 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
Very nice and clean hotel. The staff were friendly.

Reviewed on Oct 26, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was CA $3,968, price is now CA $2,615 per person
CA $2,615
per person
Jan 11 - Jan 15
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
We had an incredible stay at the Essex House last week with our two kids (one is 7 and the other turned 4 on our trip). We booked the king suite, thinking that even though it's NYC and the room will likely be small, it would be the best option for a family of 4. We were SHOCKED at the size of the suite! Not only was it enough room for all of us, it was downright roomy! We had plenty of space for our stay. The amenities and cleanliness of the hotel are superior, room service was delicious (if expensive), and best of all...the guest relations team sent a special surprise gift to our room for our 4 year olds birthday. They sent him balloons, two pieces of cake, and a bag full of stuffies and goodies. He was THRILLED and we were so touched by the thoughtfulness. Both of our kids have already asked if - not only can we go back to New York - but can we stay at the Essex House again! The location was incredible and overall the Essex House played a big part in how wonderful and effortless our trip was. Already looking at dates in the Spring to visit again! Thank you Essex House and your wonderful staff!

Reviewed on Oct 19, 2026

San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,147, price is now CA $1,435 per person
CA $1,435
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,823 reviews)
Great location and very spacious room.

Reviewed on Oct 26, 2026

Ready to book your vacation to Oyster Bay?

 

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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 $301 per night from Nov 24 to Nov 25
CA $301
CA $393 total
Nov 24 - Nov 25
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 $213 per night from Nov 22 to Nov 23
CA $213
CA $287 total
Nov 22 - Nov 23
includes taxes & fees
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 $151 per night from Nov 2 to Nov 3
CA $151
CA $179 total
Nov 2 - Nov 3
includes taxes & fees
Highbridge Hotel
See all 2,478 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.
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All Inclusive Vacations
Beach Vacations
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Family Vacations
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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 $991 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.