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.
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Price was CA $3,784, price is now CA $2,409 per person
CA $2,409
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9/10 Wonderful! (2,145 reviews)

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $7,502, price is now CA $4,308 per person
CA $4,308
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (685 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $5,678, price is now CA $3,700 per person
CA $3,700
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Manhattan
Price was CA $8,629, price is now CA $5,626 per person
CA $5,626
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9/10 Wonderful! (1,013 reviews)

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $7,206, price is now CA $4,773 per person
CA $4,773
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (651 reviews)

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Oyster Bay Hotel Deals

La Quinta Inn & Suites By Wyndham Queens NYC/JFK AirTrain

La Quinta Inn & Suites By Wyndham Queens NYC/JFK AirTrain

3 out of 5
92-16 147th Place Jamaica NY
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Aug 17 to Aug 18
CA $201
CA $241 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (818 reviews)
"What a surprise. This place looks like an upscale Marriott. Clean as can be, plenty of pillows, spacious room. Downstairs they have tables and chairs - we had food delivered and ate there. Decent selection of drinks. It was late for us so this was exceptional. We took a Uber from JFK."

Reviewed on Jul 21, 2026

La Quinta Inn & Suites By Wyndham Queens NYC/JFK AirTrain
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 $101 per night from Jul 27 to Jul 28
CA $101
CA $126 total
Jul 27 - Jul 28
includes taxes & fees
Highbridge Hotel
Hampton Inn NY-JFK

Hampton Inn NY-JFK

2.5 out of 5
144-10 135th Avenue Jamaica NY
Fully refundableReserve now, pay when you stay
The price is CA $294 per night from Aug 12 to Aug 13
CA $294
CA $348 total
Aug 12 - Aug 13
includes taxes & fees
8.2/10 Very good! (3,379 reviews)
"Great stay"

Reviewed on Jul 21, 2026

Hampton Inn NY-JFK
See all 2,463 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

Another beautiful day on one of our kayak tours

1 Hour Guided Kayak Tour in Cold Spring Harbor NY

CA $84
per adult
1 Hour Guided Kayak Tour in Cold Spring Harbor NY
Private Long Island Sound Sailing Experience

Private Long Island Sound Sailing Experience

CA $923
per traveller
Private Long Island Sound Sailing Experience
Captain Steve sails a Beneteau 343

Captain Steve's Sailing Experience on Long Island

CA $781
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 $2,409 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.

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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.