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.
Hampton Inn Madison Square Garden Area Hotel

Hampton Inn Madison Square Garden Area Hotel

3 out of 5
Manhattan
Price was CA $1,290, price is now CA $859 per person
CA $859
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.2/10 Very good! (1,515 reviews)
The hotel was good overall and budget friendly. However, limited options for breakfast especially for vegetarians.

Reviewed on Jul 10, 2026

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 20 hours 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

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 17 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,011 reviews)
Nice hotel

Reviewed on Jul 11, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,291, price is now CA $3,429 per person
CA $3,429
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 2026

Hotel AKA NoMad

Hotel AKA NoMad

4 out of 5
Manhattan
Price was CA $1,521, price is now CA $1,016 per person
CA $1,016
per person
Oct 2 - Oct 5
found 17 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
.

Reviewed on Jul 6, 2026

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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 $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! (770 reviews)
"They could have kept elevator repaired quicker. Almost 1 day it was only one elevator leading to 5 to 10 minutes of waiting"

Reviewed on Jul 11, 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! (3,409 reviews)
"The location of the hotel was very convenient. Beware of the high parking fees they charge to park in the garage at the hotel. The wait times can vary waiting for the parking attendant so make sure if you have a flight to catch to give yourself some extra time to get your car. The hotel was ok and ..."

Reviewed on Jul 11, 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! (4,304 reviews)
"Very nice rooms, clean and comfortable bed"

Reviewed on Jul 11, 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 $859 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.