Oyster Bay Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was CA $1,528, price is now CA $955 per person
CA $955
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very good! (1,710 reviews)
They don't have enough air-conditioning. The room was HOT and not in a good way.

Reviewed on Jul 12, 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $2,820, price is now CA $1,359 per person
CA $1,359
per person
Sep 13 - Sep 20
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
Luv it there

Reviewed on Jul 12, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,950, price is now CA $1,166 per person
CA $1,166
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
I’ve been to NYC many times and this location wins my business, for sure! Proximity to tons of things, rooms are gorgeous and so well maintained. Staff was extremely helpful!

Reviewed on Jul 12, 2026

Pestana CR7 Times Square

Pestana CR7 Times Square

4 out of 5
Manhattan
Price was CA $1,784, price is now CA $1,123 per person
CA $1,123
per person
Aug 19 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,011 reviews)
The staff at the front desk were so nice and friendly each day!!!

Reviewed on Jul 12, 2026

Smyth Tribeca

Smyth Tribeca

4.5 out of 5
Manhattan
Price was CA $1,565, price is now CA $988 per person
CA $988
per person
Oct 2 - Oct 5
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
The room was good but it was unclear whether the snacks and water in the room was included or not. The menu kept on the table didn't have those items in it. We were disappointed by the dirty carpets in the lift lobby on 6th floor. After checking-in past midnight, arriving on the 6th floor, the first thing we saw was the dirty, looked like coffee stained, carpet. We thought may be somebody dropped it late in the evening and it didn't get cleaned. It was there when we checked out 3 days later. While deciding on the hotel to stay we had looked at Frederick (significantly cheaper), which is just across the street, and dropped it because the reviews said "mushy smell in the rooms". Wise decision, not sure!

Reviewed on Jul 10, 2026

Ready to book your vacation to Oyster Bay?

 

Choose your dates

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 $215 per night from Aug 6 to Aug 7
CA $215
CA $252 total
Aug 6 - Aug 7
includes taxes & fees
8.8/10 Excellent! (774 reviews)
"Worked fine for our morning flight out of jfk the area is not great just fyi. Rooms are spacious."

Reviewed on Jul 12, 2026

La Quinta Inn & Suites By Wyndham Queens NYC/JFK AirTrain
Four Points by Sheraton Flushing

Four Points by Sheraton Flushing

3 out of 5
33-68 Farrington St Flushing NY
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Aug 6 to Aug 7
CA $211
CA $248 total
Aug 6 - Aug 7
includes taxes & fees
9.2/10 Wonderful! (3,411 reviews)
"The property was ok, the people in the front desk are not friendly."

Reviewed on Jul 12, 2026

Four Points by Sheraton Flushing
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 $89 per night from Jul 26 to Jul 27
CA $89
CA $107 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (4,306 reviews)
"I was in town for the Jay Z concert but I got in super early. Around 9 am when check in time is 3 pm. The desk agent got me into a room as sound as possible. I appreciate it. I am always impressed by the room cleanliness and breakfast here."

Reviewed on Jul 12, 2026

Highbridge Hotel
See all 2,457 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 $955 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.