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.
Courtyard by Marriott Lyndhurst Meadowlands

Courtyard by Marriott Lyndhurst Meadowlands

3 out of 5
Price was CA $1,315, price is now CA $841 per person
CA $841
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,009 reviews)
Mostly clean, no free anything for breakfast and staff gives you an attitude for even asking. You would think it would be included considering I spent over $500 for just two nights

Reviewed on Aug. 15, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,302, price is now CA $2,350 per person
CA $2,350
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,911, price is now CA $1,110 per person
CA $1,110
per person
Oct 26 - Oct 31
found 5 hours ago
Roundtrip flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug. 12, 2025

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was CA $1,361, price is now CA $863 per person
CA $863
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,466 reviews)
Beautiful view. Next to PATH train.

Reviewed on Aug. 22, 2025

Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Price was CA $1,529, price is now CA $996 per person
CA $996
per person
Oct 4 - Oct 8
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
7/10 Good! (2,305 reviews)
Though they could not match the price I attained through this third party site, the hotel did have accommodations and I felt safe.

Reviewed on Aug. 22, 2025

Ready to book your vacation to Oyster Bay?

 

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Oyster Bay Hotel Deals

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
The price is CA $260 per night from Sep 14 to Sep 15
CA $260
CA $290 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (2,278 reviews)
"I had a long layover rather than sticking around the airport. I came to the hotel for a few hours of sleep and took the shuttle back in the morning. The front desk agent was absolutely lovely. And it was great to have coffee and snacks to grab on the plane for breakfast."

Reviewed on Aug. 22, 2025

Five Towns Inn - JFK Airport
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 CA $206 per night from Sep 8 to Sep 9
CA $206
CA $262 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (1,628 reviews)
"Cozy room, very clean."

Reviewed on Aug. 22, 2025

Ly New York Hotel
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 $206 per night from Sep 1 to Sep 2
CA $206
CA $271 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (2,639 reviews)
"Very nice"

Reviewed on Aug. 19, 2025

Radio Hotel
See all 2,328 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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What to do in Oyster Bay

2 Hour Guided Kayak Tour in Cold Spring Harbor NY

2 Hour Guided Kayak Tour in Cold Spring Harbor NY

CA $136
per adult
2 Hour Guided Kayak Tour in Cold Spring Harbor NY
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 $841 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.

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