Oyster Bay holiday homes

We found 1,340 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Oyster Bay that are perfect for your trip. Holiday rentals offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a fireplace. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Oyster Bay

Showing deals for:2 Oct - 9 Oct

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Why visit Oyster Bay

  • Scenic Waterfront Views: Enjoy breathtaking coastal landscapes and sandy beaches that capture the charm of New York’s seafaring heritage.
  • Urban Parks & Outdoor Adventures: Explore expansive parks perfect for leisurely strolls and family picnics in a relaxed, local setting.
  • Rich Local History: Discover the cultural legacy of Oyster Bay through its historic streets and engaging local experiences.
  • Family-Friendly Atmosphere: Enjoy a welcoming town that offers activities and excursions ideal for all ages.
  • Coastal Leisure: Experience the blend of seaside relaxation with lively urban exploration in a quintessential New York setting.

Top attractions near Oyster Bay

Oyster Bay offers a delightful mix of outdoor adventures and cultural experiences, ideal for family holidays and city-themed explorations. Visitors can enjoy urban parks, sandy beaches, and national or state parks, each providing a unique blend of nature and local charm. Whether taking a leisurely stroll or enjoying the scenic coastal views, Oyster Bay promises a memorable retreat for those seeking a taste of New York's outdoor and cultural delights.

  • Oheka Castle: A stunning historic mansion with beautiful gardens, Oheka Castle offers a glimpse into the grandeur of the past. Its romantic atmosphere makes it an ideal spot for photography and leisurely strolls.
  • Huntington Beach: Known for its sandy shores and inviting waters, Huntington Beach is perfect for sunbathing, swimming, and beach games. Enjoy the vibrant beach vibes and picturesque sunsets.
  • Marshlands Conservancy: This serene wetland area features walking trails and diverse wildlife. It's a family-friendly spot where visitors can learn about local ecology while enjoying nature.

Things to do recommended for couples

Oyster Bay offers charming experiences for couples. Take a leisurely stroll along the scenic beaches, savour a romantic picnic at the beautiful Planting Fields Arboretum, or enjoy a sunset cruise on the bay. Each moment promises to create lasting memories together in this idyllic setting.

Things to do recommended for families

Families in Oyster Bay can explore the stunning trails at the nearby Oyster Bay Nature Reserve, enjoy interactive exhibits at the Raynham Hall Museum, and spend a sunny day at the local beaches, perfect for swimming and picnicking.

Things to do recommended for groups

Groups visiting Oyster Bay can enjoy a scenic tour of the historic Theodore Roosevelt Estate and take part in a fun-filled kayaking adventure on the bay. Don't miss the chance to sample local seafood at charming waterfront eateries for a true taste of the region.

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

What do I need to keep in mind when booking a vacation in Oyster Bay

When you're planning a trip, whether it's with a group, family, pets, or for an extended stay, be sure to refine your search according to your key preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Oyster Bay with a group: Consider how many bedrooms you'll need, along with features like a fully-equipped kitchen or an outdoor area for group get-togethers. Luckily, Vrbo lets you filter for all these options and more.
  • Traveling to Oyster Bay with young kids: Traveling with little ones can be a challenge. It's important to prioritise their comfort and safety, and ensure they have age-appropriate features, like access to a private pool. It's also wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oyster Bay: For many, a family holiday isn’t complete without their furry mate tagging along. If that suits you, have a look at Vrbo properties that welcome pets. Most pet-friendly options come with feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Oyster Bay: If you're searching for holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Oyster Bay

Oyster Bay, New York, offers a delightful blend of outdoor adventures and family-friendly activities. Visitors can explore its picturesque waterfront views, enjoy scenic parks, and partake in local excursions that highlight the area’s rich history. The charming atmosphere, coupled with friendly locals, makes it an ideal destination for those seeking both relaxation and engagement. Whether you're exploring the quaint streets or enjoying leisurely strolls by the water, Oyster Bay promises a memorable holiday experience.

  • Centre Island: Nestled within the Oyster Bay area, Centre Island is a charming village that offers a mix of city, business, and cultural experiences. The unique natural setting on an island provides a serene yet vibrant escape. Visitors can enjoy educational pursuits and a well-curated shopping area, all set against the backdrop of nearby beaches and family-friendly coastal venues, making it an ideal destination for those seeking a blend of leisure and urban sophistication.
  • Bayville: Located 5km from Oyster Bay, Bayville is a delightful city that caters to families, outdoor enthusiasts, and urban explorers. Its close proximity ensures easy travel while offering a rich blend of city-themed attractions, including a theatre, educational spots, and recreational areas. The local landmarks, such as the beach and event conference venues, add to its charm, providing a well-rounded holiday experience that highlights the best of coastal living.
  • Locust Valley: Also 5km away from Oyster Bay, Locust Valley presents a dynamic mix of family-friendly, outdoor, and city-themed adventures. The city is well-known for its educational offerings, vibrant music concerts, and arena-style entertainment. With local attractions featuring a beach, a modern college university, and a sports stadium, Locust Valley promises a diverse and engaging travel experience that appeals to a wide range of interests.

Best time to go to Oyster Bay

If you're planning a trip to Oyster Bay, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January32.5°F (0.3°C)Light RainMostly SunnyAverage
February33.8°F (1.0°C)Light RainMostly SunnyAverage
March40.3°F (4.6°C)Light RainMostly SunnyAverage
April50.2°F (10.1°C)Light RainMostly SunnyAverage
May60.1°F (15.6°C)Light RainMostly SunnySlightly Low
June69.3°F (20.7°C)Light RainMostly SunnyAverage
July76.3°F (24.6°C)Light RainMostly SunnySlightly High
August75.4°F (24.1°C)Light RainMostly SunnySlightly High
September68.9°F (20.5°C)Light RainMostly SunnySlightly High
October58.6°F (14.8°C)Light RainMostly SunnyAverage
November47.3°F (8.5°C)Light RainMostly SunnySlightly Low
December39.2°F (4.0°C)Light RainMostly SunnySlightly Low

Booking with Vrbo is a breeze

If you're keen to save some cash on your upcoming trip, consider keeping your travel dates flexible – prices do vary. Also, booking a longer stay can often lead to significant savings. To find the perfect Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy area where you can easily create new journeys, continue with your previous plans, or review and organise your itineraries. Your saved or booked properties are neatly sorted into Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

The charming city of Oyster Bay awaits you

Learn about the unique charm of Oyster Bay with a stay in a holiday home rental. Travellers to this romantic city praise the horse riding, shopping and restaurants. Bronx Zoo and Citi Field are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Oyster Bay

Do you want to find attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Oyster Bay a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bronx Zoo (18.2 mi / 29.2 km)
  • Cold Spring Harbor Laboratory (3.3 mi / 5.3 km)
  • Bayville Adventure Park (3.6 mi / 5.9 km)
  • Harbor Links Golf Course (7.8 mi / 12.6 km)
  • Bethpage Black State Park Golf Course (9.8 mi / 15.8 km)
  • Rye Playland (9.9 mi / 15.9 km)

Exploring the natural landscape of Oyster Bay

Whether you're an outdoor enthusiast or just want to take in the scenery, Oyster Bay is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Flushing Meadows-Corona Park (18.5 mi / 29.8 km)
  • Theodore Roosevelt Memorial Park (0.3 mi / 0.5 km)
  • Planting Fields Arboretum State Historic Park (1.6 mi / 2.5 km)
  • Cold Spring Harbor State Park (3.8 mi / 6.2 km)
  • Caumsett State Historic Park Preserve (4.5 mi / 7.3 km)
  • Cantiague Park (7 mi / 11.3 km)

Transport options to and around Oyster Bay

The nearest airport is in Farmingdale, NY (FRG-Republic), located 11.4 mi (18.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to White Plains, NY (HPN-Westchester County), which is 16.3 mi (26.2 km) away.

If you'd prefer to travel by train, you can make your way to Oyster Bay Station.

Frequently asked questions

What is the best area to stay in Oyster Bay when booking a holiday home?
One of the most sought-after areas to get an Oyster Bay holiday home is Centre Island. When you lock in your holiday property with Bookabach, you can look forward to having the entire place to yourselves. That means you don't have to share it with anybody other than your favourite people.
What is the most popular type of holiday home accommodation in Oyster Bay?
Houses are the most popular type of holiday home in Oyster Bay, according to our data. Even if you have a different vision in mind, Bookabach has holiday homes in a variety of shapes and sizes. Browse our many options to find your perfect fit.
How much does it cost to rent a holiday home in Oyster Bay?
Different things determine the price of a holiday home in Oyster Bay, such as the type of property, length of stay and season. However, all our holiday homes have something in common — incredible value. Simply add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Oyster Bay?
The average price for a holiday home near the beach in Oyster Bay depends on when you're travelling and the size and type of property you're looking for. Find prices easily and quickly on Bookabach by entering your travel dates. Then make use of the filter tool to select the number of bedrooms and amenities important to you, such as WiFi, air conditioning and a hot tub.
What are popular home amenities in Oyster Bay?
Some of the most popular home amenities guests are looking for in Oyster Bay include nearby museums, a barbecue grill and a water view. Whether you're on the road with family, buddies or even pets, Bookabach holiday homes provide the best amenities for chilling out with the people you cherish the most.
What are the top attractions for families in Oyster Bay?
Keep the kids occupied at these leading family-friendly attractions in Oyster Bay:

  • Bayville Adventure Park
  • Theodore Roosevelt Sanctuary
  • Castle Gould

Are there holiday homes with WiFi in Oyster Bay?
Whether you want to keep up with the latest news, look over emails or surf social networks, there are three holiday homes with WiFi in Oyster Bay. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How old do you have to be to rent a holiday home in Oyster Bay?
Age restrictions can vary across properties on Bookabach, so look at the rules of the holiday home in Oyster Bay you want to book. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Oyster Bay for?
The length of time you can rent a holiday home in Oyster Bay differs according to the property. Simply enter your preferred dates to view a list of options offering extended stays. With many creature comforts such as kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get a perfect place to call your home away from home in Oyster Bay.