Oyster Bay holiday rentals

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: Enjoy picturesque views at Oyster Bay Harbour, perfect for leisurely walks and family outings.
  • Historical Exploration: Visit Raynham Hall, a significant site showcasing the area's rich history and heritage.
  • Outdoor Activities: Engage in a variety of outdoor adventures, including picnics and nature walks in urban parks and beaches.
  • Charming Streets: Wander through quaint streets filled with unique local shops and a vibrant community atmosphere.
  • Family-Friendly Environment: Experience a welcoming vibe, making it an ideal destination for both families and couples.

Popular types of accommodation in Oyster Bay

Welcome to Oyster Bay, New York, a charming destination brimming with history and natural beauty. Explore the scenic waterfront, visit the historic Raynham Hall, and enjoy leisurely strolls along the picturesque beaches. With a variety of accommodation options, including apartments, private holiday homes, and condos, you’ll find the perfect holiday rental to suit your needs. Experience the quaint charm and vibrant local culture during your stay in beautiful Oyster Bay.

  • Apartments: The most sought-after lodging type in Oyster Bay, offering cosy and convenient urban living.
  • Private Holiday Homes: Ideal for families and groups, these secluded retreats provide ample space and privacy.
  • Condos: Modern and stylish, these compact accommodations blend comfort with a touch of contemporary design.
  • Cottages: Quaint and charming, perfect for those seeking a rustic, countryside experience.
  • Villas: Luxurious and spacious, these elegant homes offer a premium holiday experience.**

Top attractions near Oyster Bay

Oyster Bay offers a delightful blend of urban parks, beaches and national state parks, perfect for outdoor enthusiasts, families and culture seekers. Discover scenic strolls, rejuvenating picnics and enriching cultural experiences in this charming city. Whether you are exploring the natural beauty or enjoying the vibrant urban life, Oyster Bay provides a memorable holiday experience within its welcoming surroundings.

  • Oheka Castle: A historical castle exuding culture and romance, located 8km from Oyster Bay, offering a glimpse into grand architecture and stately gardens.
  • Rye Playland: An amusement park with outdoor adventure and family-friendly attractions, situated 16km from Oyster Bay, perfect for exhilarating rides and seaside charm.
  • Cold Spring Harbor State Park: An urban park with city vibes and family outdoor spaces, found 6km from Oyster Bay, ideal for leisurely strolls and picnics.

Things to do recommended for couples

Planning a romantic escape in Oyster Bay? Delight in a charming local experience. Stroll hand-in-hand along scenic waterfront paths, explore quaint local cafés, and enjoy a memorable sunset cruise in this picturesque town.

Things to do recommended for families

Families will delight in exploring the scenic Oyster Bay Nature Reserve, where children can engage with local wildlife. Enjoy a leisurely stroll along the picturesque waterfront or take a boat tour to discover the charming coastline and its historic maritime heritage.

Things to do recommended for groups

In Oyster Bay, groups may explore the historic Sagamore Hill, enjoy a scenic harbour cruise, and sample local flavours at community markets for a memorable, authentic 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 travelling with a group, as a family, bringing your pets along, or seeking longer stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful booking tips from Stayz.

  • Traveling to Oyster Bay with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Stayz.
  • Traveling to Oyster Bay with young kids: Traveling with young children can be challenging. You must ensure their comfort and safety while providing age-appropriate facilities, such as a private swimming pool. It's also advisable to consider your closeness to family-friendly attractions.
  • Taking your pets with you to Oyster Bay: For many, a family holiday isn't truly fulfilling unless their four-legged companion is along for the journey. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Oyster Bay: If you’re seeking holiday lets offering special rates for stays of a month or more, you’ve come to the right place. Use the appropriate filter to effortlessly discover and save on monthly rentals. You might also consider including options such as a parking space, a well-equipped kitchen or a private pool in your search.

Where to stay in Oyster Bay

Oyster Bay offers a delightful blend of outdoor adventures and city excitement. Wander through the charming streets and explore the scenic Oyster Bay harbour, with its inviting NY beach perfect for family-friendly outings. The town's mix of business and leisure atmospheres ensures a memorable visit, where friendly locals and a relaxed vibe make it an ideal destination for a family or romantic escape. Discover the best of Oyster Bay and create lasting memories in this enchanting city.

  • Oyster Bay Cove: Nestled in the heart of Oyster Bay, Oyster Bay Cove is a charming village that promises a delightful blend of outdoor, family, and culture-themed experiences. Visitors can enjoy scenic recreational areas and bustling shopping districts alongside a delightful theatre for cultural evenings. Its coastal charm is evident with local landmarks such as sandy beaches, verdant parks, and family-friendly beach spots, making it a perfect escape for those seeking both relaxation and vibrant community life.
  • Centre Island: Situated in the Oyster Bay area, Centre Island is a unique village naturally graced by its island setting. It offers a dynamic mix of city and business-themed experiences alongside cultural elements. The area is well-known for its educational facilities and shopping areas, ensuring a stimulating visit. Among its attractions, visitors can explore pristine beaches, family-friendly beach areas, and versatile venues, all contributing to a rich and fulfilling travel experience.
  • Cove Neck: Located within Oyster Bay, Cove Neck is a quaint village offering a harmonious blend of culture, outdoor pursuits, and scenic views. It is renowned for its golfing opportunities, with accessible courses and recreational areas that invite both novices and seasoned players. In addition, the local area features significant attractions including museums, historic sites, and charming hills, providing a culturally enriched and picturesque setting for every visitor.

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. Peak season runs from July to September, while off-peak times, like May and November to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 SunnyAverageSlightly High
July76.3°F (24.6°C)Light RainMostly SunnySlightly HighSlightly High
August75.4°F (24.1°C)Light RainMostly SunnySlightly HighSlightly High
September68.9°F (20.5°C)Light RainMostly SunnySlightly HighAverage
October58.6°F (14.8°C)Light RainMostly SunnyAverageAverage
November47.3°F (8.5°C)Light RainMostly SunnySlightly LowAverage
December39.2°F (4.0°C)Light RainMostly SunnySlightly LowAverage

Booking with Stayz is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Furthermore, extending your stay often results in significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board provides you with a dedicated space to create new journeys, continue with your plans, or review and organise your bookings. Properties you have either saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.stayz.com.au/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 Stayz, 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, Stayz 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 Stayz 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, Stayz 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 Stayz 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 Stayz, 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.

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