Oyster Bay Vacations from ￥372,930

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The Latest Oyster Bay Vacation Packages

Price found within the past 48 hours. Click for updated prices.
OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was ￥521,828, price is now ￥372,930 per person
￥372,930
per person
Oct 8 - Oct 15
found 3 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to New York (JFK)
6.8/10 (1,983 reviews)
Everything went well and was nice to restaurant and bars.

Reviewed on Jul 16, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥730,823, price is now ￥460,823 per person
￥460,823
per person
Oct 8 - Oct 15
found 3 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
Great location for first timers to the city! It’s right in the middle of midtown. Awesome breakfast!

Reviewed on Jul 17, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥721,228, price is now ￥456,350 per person
￥456,350
per person
Oct 8 - Oct 15
found 3 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to New York (JFK)
9.2/10 Wonderful! (3,746 reviews)
The staff was very nice and helpful. The breakfast was great, even for me, who eats gluten-free. The hotel's location is excellent. In short, a highly recommended hotel.

Reviewed on Jul 17, 2026

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was ￥589,114, price is now ￥422,136 per person
￥422,136
per person
Oct 8 - Oct 15
found 3 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to New York (JFK)
9/10 Wonderful! (4,331 reviews)
Tropical oasis in Times Square,

Reviewed on Jul 17, 2026

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Price was ￥555,755, price is now ￥402,198 per person
￥402,198
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (2,127 reviews)
Excellent location

Reviewed on Jul 15, 2026

Find the Best Oyster Bay Vacation Packages

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 ￥21,772 per night from Aug 16 to Aug 17
￥21,772
￥26,118 total
Aug 16 - Aug 17
includes taxes & fees
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 ￥25,572 per night from Aug 4 to Aug 5
￥25,572
￥30,482 total
Aug 4 - Aug 5
includes taxes & fees
9.2/10 Wonderful! (3,395 reviews)
"This was a nice hotel, clean room, mini fridge, iron and ironing board available. Large screen TV, comfortable beds. I would definitely stay there again. The free shuttle from the airport was great!"

Reviewed on Jul 17, 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 ￥11,690 per night from Jul 27 to Jul 28
￥11,690
￥14,551 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (4,324 reviews)
"My stay was decent! Close to the stadium so very convenient. Free breakfast served in the morning, but you have to eat it in the dining area. It was very clean, friendly staff and the AC worked."

Reviewed on Jul 17, 2026

Highbridge Hotel
See all 2,461 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.

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)
Theodore Roosevelt's grand Victorian mansion offers an intimate glimpse into the 26th president's personal life. Tour the meticulously preserved home with original furnishings and explore the surrounding natural estate.
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

￥9,590
per adult
1 Hour Guided Kayak Tour in Cold Spring Harbor NY
Private Long Island Sound Sailing Experience

Private Long Island Sound Sailing Experience

￥105,651
per traveler
Private Long Island Sound Sailing Experience
Captain Steve sails a Beneteau 343

Captain Steve's Sailing Experience on Long Island

￥89,397
per traveler
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 ￥372,930 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?
Travel in the low season and you're likely to get cheap Oyster Bay vacation packages. Remember that public holidays and local events and festivals can impact prices, so do a little research before you go.
How many days is enough for Oyster Bay?
Typically, a handful of days is ideal for an Oyster Bay vacation. With a well-planned itinerary, you can check out all the popular sights like Theodore Roosevelt Memorial Park, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Oyster Bay?
Oyster Bay is a good vacation destination with attractions like Theodore Roosevelt Sanctuary and Audubon Center among the many things to keep you busy. Whether you're heading away 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 your dates: What you'd like to do in Oyster Bay and your preferred season will help you decide when to travel.
  2. Budget wisely: As well as the price of your accommodations, you should factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that could arise during your trip to Oyster Bay.
  3. Decide your trip length: Think about how long 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 comfortable pace.
  4. Combine your airfare and accommodations: After you've settled on your dates and duration, lock in the ideal Oyster Bay vacation package for you.

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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.