Oyster Bay Vacations from $284

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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.

The Latest Oyster Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,096 reviews)
We only stayed 1 night. We attended the Zach Bryan concert. We thought the room was very spacious, but outdated. The comforter had what looked like cigarette burns in it. Room was clean, but bathroom needs updating. Only had a small body of shampoo, shower took like 5 minutes to get hot, and I felt like the floor in the tub was sinking. We did however appreciate how friendly the staff was, that the ac worked, and how close to the venue it was.

Reviewed on Jul 19, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (480 reviews)
Had a wonderful time at Harbor Front Inn. Two small suggestions would make my retutn stay even more wonderful. Decafe needs to be hot. It was lukewarm every morning. Two more umbrellas around the pooL would be very welcome. These things are not enough to discourage us from returning.

Reviewed on Jul 17, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul 10, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Very tiny room with no good light, could barely see there. Also blanket doesnt have a cover up. No proper bathroom.

Reviewed on Jul 17, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
per person
Sep 30 - Oct 3
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul 18, 2025

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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

Comfort Inn JFK Airport

Comfort Inn JFK Airport

2.5 out of 5
132-15 150th Avenue, Jamaica, NY
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $250 total per night from Aug 10 to Aug 11
$250 total
Aug 10 - Aug 11
Total includes taxes and fees
8/10 Very Good! (4,722 reviews)
"Good because it's close to the airport"

Reviewed on Jul 18, 2025

Comfort Inn JFK Airport
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
$134 nightly
The price is $154 total per night from Aug 10 to Aug 11
$154 total
Aug 10 - Aug 11
Total includes taxes and fees
8.2/10 Very Good! (1,009 reviews)
"Hotel was clean and modern. Lobby had snacks and drinks. Water on all floors. Friendly staff. Will return"

Reviewed on Jul 17, 2025

EVEN Hotel Norwalk by IHG
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave, New York, NY
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $162 total per night from Jul 31 to Aug 1
$162 total
Jul 31 - Aug 1
Total includes taxes and fees
8.6/10 Excellent! (2,591 reviews)
"We stayed at this hotel as part of a package with flight and accommodation. The hotel is clean, cozy, and nicely designed. The reception staff were very friendly and welcoming, which made a great impression. Upon check-in, we received drink vouchers — a lovely bonus. We arrived at 3 AM due to a flight ..."

Reviewed on Jul 16, 2025

Radio Hotel
See all 2,273 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

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Frequently asked questions

How much does an Oyster Bay vacation package cost?
You'll find cheap prices from $284 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.