Oyster Bay Vacations from $296

Book a Hotel + Flight or Car together to unlock savings

Photo by Wanderlust Nomad

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.

The Latest Oyster Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $574, price is now $296 per person
$296
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Stayed in for one night and the room was beautiful. The bed was beyond comfortable and clean. From the check in to check out, staff was very helpful. 100% will recommend.

Reviewed on Oct 25, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $904, price is now $486 per person
$486
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,030 reviews)
The staff were super welcoming, it was a large hotel room on the top floor. Would definitely stay here again!

Reviewed on Oct 30, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,816, price is now $1,003 per person
$1,003
per person
Dec 5 - Dec 7
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,333 reviews)
Room was very clean, but the bed could use a new mattress and the shower only had mediocre pressure. All in all, great for a one night stay, would probably stay here again.

Reviewed on Oct 27, 2025

The Mansion at Glen Cove

The Mansion at Glen Cove

4 out of 5
Save 100% on your flight
Price was $627, price is now $355 per person
$355
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7/10 Good! (1,001 reviews)
perfect stay. love the nature and the vibe there. will be best for vacation.

Reviewed on Nov 2, 2025

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Save 100% on your flight
Price was $837, price is now $487 per person
$487
per person
Jan 7 - Jan 12
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (24 reviews)
We wanted a clean room to sleep. It was quite clean. Out expectations were met. Staff was very nice and helpful. Shared bathroom was not a problem.

Reviewed on Oct 12, 2025

Don't see what you're looking for?
See all available trips from Columbus to Oyster Bay
View all trips

Discover the most popular places to visit in Oyster Bay

Theodore Roosevelt’s Home in Oyster Bay

Sagamore Hill National Historic Site

4.5/5(16 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.

Sagamore Hill National Historic Site
It's always beautiful whenever you visit, the park has its special beauties showed to public Year around.

Planting Fields Arboretum State Historic Park

5/5(1 review)

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.

Planting Fields Arboretum State Historic Park

Theodore Roosevelt Memorial Park

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 Memorial Park

Oyster Bay Hotel Deals

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
$189 nightly
The price is $220 total per night from Nov 3 to Nov 4
$220 total
Nov 3 - Nov 4
Total with taxes and fees
9/10 Wonderful! (2,694 reviews)
The only thing I didn't like was that they didn't make the bed.

Reviewed on Oct 28, 2025

Four Points by Sheraton Flushing
The Parc Hotel

The Parc Hotel

2.5 out of 5
3916 College Point Blvd, Flushing, NY
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $147 total per night from Nov 16 to Nov 17
$147 total
Nov 16 - Nov 17
Total with taxes and fees
7.8/10 Good! (1,757 reviews)
I arrived early and was told for a small fee they could get me into a different room. The room itself was fine but I definitely did not get the view you see in the photos. I love flying so having the planes pass overhead was a bonus for me. I also visited the rooftop bar and the bartender was nice ...

Reviewed on Oct 28, 2025

The Parc Hotel
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
$142 nightly
The price is $167 total per night from Nov 4 to Nov 5
$167 total
Nov 4 - Nov 5
Total with taxes and fees
8.8/10 Excellent! (1,790 reviews)
The room was great. Parking sucked but welcome to NY.

Reviewed on Oct 28, 2025

Ly New York Hotel
See all 2,464 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.

Find the Best Oyster Bay Vacation Packages

Oyster Bay Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
6,700
Max Temp Winter
40ºF
Max Temp Summer
80ºF
Top Sights
Adventureland, NYCB Theatre at Westbury and Eisenhower Park

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Oyster Bay vacation package cost?
You'll find cheap prices from $296 on Expedia for your Oyster Bay escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Oyster Bay costs.
What are the cheapest months to go to Oyster Bay?
December, January and February are the best times to search for cheap Oyster Bay vacation packages. Choosing to travel in quieter periods means you can typically find lower prices on flights and hotels.
How many days is enough for Oyster Bay?
You can visit all the main attractions in Oyster Bay within a few days, including the must-see Sagamore Hill National Historic Site. If you want a longer Oyster Bay vacation, check out what kind of activities and day trips are available close by.
Is it worth booking a vacation package to Oyster Bay?
Oyster Bay is a good vacation destination with attractions like Sagamore Hill National Historic Site among the many things to keep you busy. Whether you're traveling with the family or planning a trip with friends, an Oyster Bay vacation promises a good time for everyone.
How to find the best Oyster Bay package deals?
Begin your search for an Oyster Bay package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Oyster Bay package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oyster Bay escape off to a flying start.
Is it cheaper to book an Oyster Bay vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Oyster Bay vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Oyster Bay?
If you're considering a spur-of-the-moment Oyster Bay adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Oyster Bay?

  1. Choose when to go: Check your schedule and pack your bags. Your favorite time of year and the type of activities available will also help you decide when to visit Oyster Bay.
  2. Set a budget: Factor in costs like transportation, flights and meals when working out how much to put aside for your trip to Oyster Bay. Then, choose a property that suits your budget, whether that's a low-cost option or a swankier retreat.
  3. Use our trip planning tool to explore Oyster Bay: Research every aspect of your trip to Oyster Bay with this handy planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Work out your trip length: Think about how much time you'd like to spend discovering Oyster Bay. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Oyster Bay vacation package.
  6. Book any day trips or activities: Now to the fun part — locking in everything you want to see and do. Explore some of the incredible things to do in Oyster Bay and reserve your tickets early to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Oyster Bay vacation packages?
Set off on your perfect escape to Oyster Bay with our Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snag great deals before they disappear.

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.