Photo by Wanderlust Nomad

Oyster Bay holiday homes

We found 1,341 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 Jan - 9 Jan
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Oyster Bay

  • Beautiful Beaches: Enjoy the sandy shores at Oyster Bay beach resort and Oyster Pond, perfect for sunbathing and swimming.
  • Scenic Coastal Views: Discover the stunning ocean vistas along the Marlborough Coast, ideal for nature lovers.
  • Family-Friendly Activities: Engage in outdoor adventures and explore local parks, making it a great destination for families.
  • Charming Town Atmosphere: Stroll through the quaint town of Oyster Bay, filled with friendly locals and unique shops.
  • Cultural Experiences: Immerse yourself in the local college vibe and partake in various cultural events.

Top attractions near Oyster Bay

Oyster Bay, New York, offers a fantastic blend of outdoor activities and family-friendly attractions. You can explore the beautiful Oyster Bay beach resort, enjoy the sandy shores at Oyster Pond, or visit the local urban parks. The area also boasts a modern college and university atmosphere, making it perfect for cultural experiences. Don't miss the charming town of Oyster Bay while you’re there.

  • Oheka Castle: Nestled 8.0km from Oyster Bay, this stunning castle offers a glimpse into a bygone era with its romantic architecture and lush gardens, perfect for a fairy-tale experience.
  • Huntington Beach: Located 12.9km away, this beautiful beach boasts golden sands and vibrant beach vibes, ideal for sunbathing, swimming, or simply enjoying the coastal scenery.
  • Marshlands Conservancy: Situated 17.7km from Oyster Bay, this tranquil wetland features rich cultural and historical significance, making it a family-friendly spot for nature walks and wildlife observation.

Things to do recommended for couples

Oyster Bay offers delightful experiences for couples. Enjoy a romantic day at Del Vino Vineyards, unwind with rejuvenating treatments at Hand & Stone Massage and Facial Spa, or have some fun at Monster Mini Golf. Each spot promises a memorable time together. Cheers to your getaway.

Things to do recommended for families

Families visiting Oyster Bay can unwind at the Charles E. Ransom Beach Dog Park, enjoy sporting activities at Chelsea Piers, or make a splash at the Nassau County Aquatic Center. Each location offers a unique experience, perfect for both relaxation and fun-filled family adventures.

Things to do recommended for groups

Groups visiting Oyster Bay can tee off at the renowned Bethpage Black State Park Golf Course, catch a show at the charming Paramount Theater, and indulge in shopping and dining at the bustling Roosevelt Field Mall for a well-rounded experience.

*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

If you're planning a trip with a group, family, pets, or looking for extended stays, be sure to prioritise your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Oyster Bay with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Oyster Bay with young kids: Travelling with young kids can be a bit tricky. It’s important to prioritise their comfort and safety, along with having suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oyster Bay: For many, a family getaway feels incomplete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oyster Bay: If you're in search of holiday rentals with discounts for stays of a month or longer, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don’t forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in and around Oyster Bay

Oyster Bay, New York, offers a delightful blend of outdoor adventures and family-friendly experiences. Explore the stunning ocean views along the Marlborough Coast, where you can discover a slice of paradise. Nearby towns provide a warm atmosphere with friendly locals, perfect for romantic strolls or budget-friendly excursions. Whether you're after a bustling city vibe or a peaceful retreat, Oyster Bay has something for every traveller keen to soak up its charm.

  • Centre Island: Centre Island is a picturesque village located within the Oyster Bay area, offering a serene island experience. The natural beauty of the beaches draws families and visitors seeking a relaxing getaway. Here, you can enjoy activities at the aquatic centre, browse through local shops, and soak up the sun on the family-friendly beaches. With landmarks such as the local stadium and scenic beach areas, Centre Island provides a delightful blend of leisure and recreation, perfect for a day of exploration.
  • Bayville: Situated a mere 4.8km from Oyster Bay, Bayville is a vibrant city known for its bustling business atmosphere and lively entertainment scene. As you wander through the shopping areas and mall centres, you'll find a plethora of dining options and local vendors. Bayville is also home to a beach and event conference venues, making it a great spot for both relaxation and engagement. Whether you’re attending a local event or simply enjoying the coastal charm, Bayville promises a dynamic urban experience.
  • Locust Valley: Also located 4.8km from Oyster Bay, Locust Valley is a family-friendly city that offers a variety of outdoor activities and community events. The town features a charming shopping area and educational opportunities, alongside cultural highlights such as theatres. With access to beautiful beaches and a vibrant tourist precinct, Locust Valley serves as an ideal destination for families looking to enjoy nature while indulging in local attractions. It’s a perfect place to unwind and create lasting memories.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Are you keen to save on your next adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to refine your search by price, location, and the type of holiday rental you prefer.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your existing arrangements, or review your bookings. Your saved or booked properties are neatly categorised into Potential, Upcoming, or Current Trips. To check out the Trip Boards, head over to: 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:

  • 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)
  • Old Westbury Gardens (7.7 mi / 12.4 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.

More Holiday Rentals ideas

People also search for