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.
East Norwich Inn
CA $966
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,809 reviews)
I arrived around 10 PM, but nobody was at the front desk. I rang the bell three times, and after about 5 minutes, a man showed up. He was unfriendly, and acted like he was angry.
Reviewed on Oct 10, 2026
33 Hotel, New York City, Seaport
Manhattan
CA $1,156
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
Great location in lower Manhattan. The hotel was comfortable, well maintained and near good restaurants and pubs. The staff was very helpful. Highly recommend staying here.
Reviewed on Oct 9, 2026
Ready to book your vacation to Oyster Bay?
Oyster Bay Hotel Deals
TWA Hotel at JFK Airport
One Idlewild Drive Jamaica NY
Fully refundableReserve now, pay when you stay
CA $354
CA $457 total
Oct 26 - Oct 27
includes taxes & fees
Radio Hotel
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
CA $295
CA $382 total
Nov 8 - Nov 9
includes taxes & fees
Highbridge Hotel
1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
CA $154
CA $182 total
Oct 19 - Oct 20
includes taxes & fees
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
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.
Planting Fields Arboretum State Historic Park
9.2/10 (7 reviews)
Take the family on an outing to Planting Fields Arboretum State Historic Park during your trip to Upper Brookville. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
Photo by Erick
Theodore Roosevelt Memorial Park
10.0/10 (2 reviews)
Explore the great outdoors at Theodore Roosevelt Memorial Park, a lovely green space in Oyster Bay. While in this family-friendly area, you can savor the top-notch restaurants.
Theodore Roosevelt Sanctuary and Audubon Center
10.0/10 (2 reviews)
You can take time to visit Theodore Roosevelt Sanctuary and Audubon Center during your travels to Oyster Bay Cove. Wander the picturesque gardens in this quaint area.
20th Century Cycles
10.0/10 (2 reviews)
You can browse the exhibits at 20th Century Cycles, a museum with a storied past, during your travels to Oyster Bay. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
Beekman Beach
8.0/10 (2 reviews)
Why not spend a lazy afternoon at Beekman Beach during your trip to Oyster Bay? While you're in the area, wander around the natural setting.
What to do in Oyster Bay
Captain Steve's Sailing Experience on Long Island
CA $763
per traveller
Frequently asked questions
How much does an Oyster Bay vacation package cost?
You'll find cheap prices from CA $966 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?
- 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.
- 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.
- 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.
- 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
