Oyster Bay Holidays from £1,287

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Your Oyster Bay Holiday

When a break in the city is calling, answer it with a Oyster Bay holiday package. The neighbourhood 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 Harbour Laboratory. Whoever you're escaping with and whatever you want to spend, your dream Oyster Bay holiday is just clicks away with Expedia.

Top Oyster Bay Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Motel Casa Downtown Guest House

Motel Casa Downtown Guest House

Central Ward
£1,287
per person
6 Dec - 12 Dec
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
6.4/10 (69 reviews)
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

£1,395
per person
6 Dec - 12 Dec
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
7.2/10 Good! (1,022 reviews)
Courtyard by Marriott Newark Liberty International Airport

Courtyard by Marriott Newark Liberty International Airport

£1,424
per person
6 Dec - 12 Dec
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
8.4/10 Very good! (1,011 reviews)
Great location for a quick stay by the airport

Reviewed on 21 Sept 2026

Home2 Suites by Hilton Rahway, NJ

Home2 Suites by Hilton Rahway, NJ

£1,465
per person
6 Dec - 12 Dec
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
Courtyard by Marriott Wayne Fairfield

Courtyard by Marriott Wayne Fairfield

£1,469
per person
6 Dec - 12 Dec
found 6 hours ago
Return flight included
London (LHR) to New York (JFK)
8.6/10 Excellent! (756 reviews)

Things to do near Oyster Bay

Oyster Bay, New York, is perfect for a family-oriented outdoor vacation, offering a variety of activities such as golf and scenic walks. Visitors can enjoy unique excursions, theme nights, and even scuba lessons. For those seeking fun in the sun, a local water park provides entertainment for all ages. With its charming city atmosphere, Oyster Bay promises a delightful getaway filled with engaging experiences.

Shopping

In Oyster Bay, you can enjoy shopping at Walt Whitman Shops, just 11.3km away, offering a variety of stores and family-friendly entertainment. If you're up for a drive, New Roc City and Stamford Town Center are both excellent options, located 13 and 19.3km away respectively, with similar vibes.

Recreation

Kings Point Park offers a tranquil escape with its picturesque landscapes, perfect for leisurely strolls and relaxation. Just a short drive away, Doral Arrowwood Golf Club provides an invigorating outdoor experience for golf enthusiasts. Meanwhile, Paramount Theater, rich in culture, offers delightful entertainment for families and couples alike.

Adventure

At Bethpage Park Tennis Center, located 16.1km from Oyster Bay, enjoy thrilling tennis matches amidst vibrant surroundings. Experience the enchanting Nunley’s Carousel, 17.7km away, perfect for a whimsical ride. For family fun, venture to New Roc n Bowl, 20.9km from Oyster Bay, featuring exciting arcade games.

Nightlife

In Oyster Bay, enjoy a charming nightlife with waterfront bars and cosy pubs. The local scene offers live music at venues like the Oyster Bay Brewing Company and laid-back evenings at bars along the bay, perfect for sipping cocktails while soaking in the scenic views.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Oyster Bay

Oyster Bay, New York, offers a delightful mix of outdoor activities, family-friendly attractions, and urban charm. Visitors can enjoy the scenic Oyster Bay Beach, explore local beach villas, and relax by Oyster Pond. The area is perfect for those seeking a blend of nature and city life, with modern universities and beautiful parks enhancing the experience. Don't miss the chance to discover the nearby beaches of Jamaica, making for a memorable holiday.

  • Rye Playland: Located 16.1km from Oyster Bay, Rye Playland is a charming amusement park offering thrilling rides and attractions for families. With its outdoor adventure vibes, you can enjoy everything from classic roller coasters to carnival games, all set against a picturesque waterfront backdrop.
  • Sands Point Preserve: Just 14.5km from Oyster Bay, this historic house and estate is steeped in culture. Visitors can explore beautifully landscaped gardens, historic architecture, and captivating views of Long Island Sound, making it a perfect spot for history enthusiasts and nature lovers alike.
  • Eisenhower Park: Situated 16.1km away, this expansive state park is a haven for outdoor adventure seekers. With scenic walking trails, sports facilities, and picnic areas, it offers stunning landscapes and recreational opportunities for all ages.

Best time to go to Oyster Bay

The best time to visit Oyster Bay is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.5°F (0.3°C)Light RainMostly SunnyAverageSlightly Low
February33.8°F (1.0°C)Light RainMostly SunnyAverageSlightly Low
March40.3°F (4.6°C)Light RainMostly SunnyAverageSlightly Low
April50.2°F (10.1°C)Light RainMostly SunnyAverageAverage
May60.1°F (15.6°C)Light RainMostly SunnySlightly LowAverage
June69.3°F (20.7°C)Light RainMostly SunnyAverageAverage
July76.3°F (24.6°C)Light RainMostly SunnySlightly HighAverage
August75.4°F (24.1°C)Light RainMostly SunnySlightly HighAverage
September68.9°F (20.5°C)Light RainMostly SunnySlightly HighSlightly High
October58.6°F (14.8°C)Light RainMostly SunnyAverageSlightly High
November47.3°F (8.5°C)Light RainMostly SunnySlightly LowAverage
December39.2°F (4.0°C)Light RainMostly SunnySlightly LowSlightly High

Tips to save on your trip to Oyster Bay

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Oyster Bay.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Oyster Bay.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Oyster Bay Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
6,700
Max Temp Winter
4ºC
Max Temp Summer
27ºC
Top Sights
NYCB Theatre at Westbury, Adventureland and Eisenhower Park

Top hotels in Oyster Bay

TWA Hotel at JFK Airport

TWA Hotel at JFK Airport

One Idlewild Drive Jamaica NY
Fully refundableReserve now, pay when you stay
£244
6 Oct - 7 Oct
includes taxes & fees
TWA Hotel at JFK Airport
Radio Hotel

Radio Hotel

2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
£186
27 Sept - 28 Sept
includes taxes & fees
8.4/10 Very good! (2,414 reviews)
"Great hotel located 8 minutes from Columbia hospital."

Reviewed on 21 Sept 2026

Radio Hotel
La Quinta Inn & Suites By Wyndham Queens NYC/JFK AirTrain

La Quinta Inn & Suites By Wyndham Queens NYC/JFK AirTrain

92-16 147th Place Jamaica NY
Fully refundableReserve now, pay when you stay
£156
30 Sept - 1 Oct
includes taxes & fees
8.8/10 Excellent! (1,137 reviews)
"Nice hotel, the room I had was clean, spacious. Staff were helpful. I would book with them again."

Reviewed on 22 Sept 2026

La Quinta Inn & Suites By Wyndham Queens NYC/JFK AirTrain
See all 2,442 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.
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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

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
A grove of cherry blossom trees with pink flowers.

Planting Fields Arboretum State Historic Park

9.2/10 (7 reviews)
Explore 409 acres of historic gardens and Tudor Revival Coe Hall mansion at Planting Fields Arboretum. The meticulously maintained greenhouses feature the Northeast's largest camellia collection.
See properties
A beach with people, a large yellow duck sculpture, and a clear sky with clouds.
Photo by Erick

Theodore Roosevelt Memorial Park

10.0/10 (2 reviews)
This waterfront park honours the 26th President with scenic bay views and recreational spaces. Enjoy the sandy beach, tennis courts, or attend the annual Oyster Festival celebrating local culture.
See properties

Theodore Roosevelt Sanctuary and Audubon Center

10.0/10 (2 reviews)
America's first songbird sanctuary offers peaceful trails through native gardens and woodlands in historic Oyster Bay. Bring binoculars to spot Black-capped Chickadees while exploring the mile-long nature paths.
See properties

20th Century Cycles

10.0/10 (2 reviews)
Explore Billy Joel's personal collection of 75+ vintage motorcycles at this free weekend museum in Oyster Bay. Enthusiasts will appreciate the meticulous restorations and staff sharing stories behind each unique bike.
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Beekman Beach

8.0/10 (2 reviews)
Why not spend a lazy afternoon at Beekman Beach during your trip to Oyster Bay? While you're in the area, wander around the natural setting.
See properties

What to do in Oyster Bay

Private Long Island Sound Sailing Experience

Private Long Island Sound Sailing Experience

£476
per traveller
Private Long Island Sound Sailing Experience
See all activities in Oyster Bay

Frequently asked questions

Why should I book my Oyster Bay holiday with Expedia?
Expedia has your back for all aspects of your Oyster Bay getaway. You'll always land the best deals, but when you bundle your accommodation, airfares and/or car hire into a holiday package, you'll score even bigger savings. Looking to really make the most of your escape? Add some exciting tours and activities to your customised package. Expedia offers flexible cancellation policies on almost all bookings, so you won't need to worry if your travel plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Oyster Bay?
Oyster Bay can get busy in May, June and July, so if you want to avoid the crowds, travel in December, January and February. Plan your trip to Oyster Bay according to what style of adventure you want. January is the coolest time of year, when average daytime temperatures are 0ºC. In July, the warmest month, you can expect averages of 24ºC during the day.
What are the top hotels for my holiday in Oyster Bay?
Presidential Victorian Mansion in the Oyster Bay Cove neighbourhood is a top choice for an Oyster Bay getaway. Lock in a room here and you'll be perfectly placed to explore all that this vibrant city has to offer.
How do I get a cheap holiday to Oyster Bay?
Bundle your hotels and flights with Expedia to save on your next trip. With over 400 airlines and 321,000 properties throughout the world, your Oyster Bay holiday can be customised exactly to suit your budget. With all those extra pounds, why not add some fun experiences and tours? It's an easy way to unlock even more discounts. The holiday you've always dreamed of in Oyster Bay is much closer than you thought! Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Oyster Bay holiday?
Make sure your holiday in Oyster Bay is one to remember by stopping by its leading attractions. NYCB Theatre at Westbury, Long Island University Post Campus, Cold Spring Harbour Laboratory and Sands Point Preserve are among the things we recommend seeing while you're in the area.
Do I need a visa for my Oyster Bay holiday?
Official government websites are the best source of information on visa requirements, application procedures and necessary documentation. Your nationality and the reason for your visit, whether it be for tourism or work, will determine if you'll need a visa for Oyster Bay. Be sure that your passport is up to date and has a minimum of six months validity remaining beyond your date of return. Finalise all your travel planning well ahead of time to avoid any last-minute surprises.
What should I wear on my Oyster Bay holiday?
Do a little research into the types of clothing people in Oyster Bay wear, and maybe even browse fashion pages on social media for inspiration. You'll want to create a versatile travel wardrobe with pieces that suit your destination and show off your personal style.
What does an Expedia Oyster Bay holiday include?
Expedia has all you need to organise your Oyster Bay getaway, but how you structure your package is your choice. Pick from any combination of hotels, flights and hire cars. Searching for some tours or experiences to keep you busy? Once you've made your booking, you can add them on too. No matter your style or budget, there's a deal to meet your needs. Private holiday homes and hotel resorts are a few popular property types in Oyster Bay. No matter your preference or size of your group, you can count on Expedia for the freedom and flexibility to personalise your escape.
Does Expedia offer Book Now, Pay Later Oyster Bay holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has devised a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a terrific getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Consider one of these flexible payment options:
  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's easy payment plans. If making bite-sized repayments each month works for you, pick this option during the checkout process.
  • No-deposit holidays: When you come across an unbeatable deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.
Can I choose my airline with an Oyster Bay Expedia holiday?
Yes, the choice is all yours. We offer more than 400 airlines globally, so you can tailor your Oyster Bay adventure according to your needs and budget.

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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. Flight-inclusive packages are ATOL protected.