Photo by Wanderlust Nomad

Oyster Bay holiday lettings

We found 1,260 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other 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:3 Oct - 10 Oct

Why visit Oyster Bay

  • Outdoor Adventures: Oyster Bay is perfect for nature enthusiasts, offering parks, beaches, and scenic excursions that highlight the area’s natural beauty.
  • Family-Friendly Activities: The destination caters to families with various engaging activities suitable for all ages, ensuring a memorable experience.
  • Charming Neighbourhoods: Explore nearby towns like Glen Cove and Lattingtown, known for their picturesque settings and romantic spots.
  • Diverse Accommodation: A wide range of holiday rentals, from apartments to beachfront homes, provides tailored options for every traveller.
  • Welcoming Atmosphere: Friendly locals enhance the experience, making visitors feel at home in this delightful coastal town.

Popular types of accommodation in Oyster Bay

Oyster Bay offers an enticing selection of vacation rentals, including apartments, private homes, and condos, perfect for any traveller. Whether you're seeking a charming house rental, a spacious holiday home, or a beachfront retreat, you'll find options to suit your preferences. With a focus on transparency and savings, our platform ensures you can book your ideal Oyster Bay house holiday rental with confidence.

  • Apartments: The most sought-after choice for holiday rentals in Oyster Bay, perfect for those seeking convenience and comfort.
  • Houses: A popular selection for families or groups, offering a home-like atmosphere and privacy.
  • Condos: Ideal for those wanting a blend of amenities and space, making them a great option for a relaxing stay.
  • Cottages: A delightful option for a quaint getaway, providing a charming and snug environment.
  • Villas: The ultimate luxury accommodation, offering spacious living and stunning surroundings.**

Top attractions in and around Oyster Bay

Oyster Bay, New York, is an ideal destination for outdoor and family-oriented holidays, offering a blend of urban parks, beaches, and modern educational institutions. Visitors can enjoy a variety of attractions that cater to those seeking both city experiences and natural beauty. Whether you're travelling solo or with family, there's plenty to explore in and around Oyster Bay, making it a perfect spot for a memorable vacation.

  • Sagamore Hill National Historic Site: This historic house was the home of President Theodore Roosevelt and offers a glimpse into his life and legacy. Visitors can explore the beautifully preserved rooms and learn about the cultural history of the era, surrounded by scenic grounds.
  • Long Island University Post Campus: A modern university with a vibrant atmosphere, just 3.1km from Oyster Bay. The campus boasts impressive architecture and lush landscapes, making it an ideal spot for a leisurely stroll or a quiet study session.
  • Planting Fields Arboretum State Historic Park: A stunning arboretum featuring diverse gardens and outdoor spaces perfect for families. Enjoy leisurely walks among the flora and participate in seasonal events that celebrate nature.

Things to do recommended for couples

For a romantic getaway in Oyster Bay, indulge in a soothing treatment at Hand & Stone Massage and Facial Spa, just 8.7km away. Enjoy a fun round of mini-golf at Monster Mini Golf, also 8.7km away, before savouring delightful wines at Harmony Vineyards, 12.4km away.

Things to do recommended for families

Families visiting Oyster Bay can splash around at the Nassau County Aquatic Center, enjoy various sports at Chelsea Piers, or unwind at the Plainview-Old Bethpage Community Park, perfect for wellness and relaxation. Each destination offers a delightful experience for all ages.

Things to do recommended for groups

Groups visiting Oyster Bay can indulge in retail therapy at Roosevelt Field Mall, catch a show at the Paramount Theater, or enjoy a round of golf at the Bethpage Black State Park Golf Course, all offering unique experiences and vibrant atmospheres for everyone.

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming getaway? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Where to stay in and around Oyster Bay

Oyster Bay offers a delightful blend of outdoor adventures and family-friendly activities, making it an ideal destination for all types of travellers. Explore nearby towns such as Glen Cove and Lattingtown, where charming neighbourhoods and romantic spots await. Enjoy excursions that showcase the area's natural beauty, while friendly locals add to the welcoming atmosphere. Whether you're seeking budget-friendly options or a touch of elegance, Oyster Bay and its surroundings promise a memorable getaway.

  • Mill Neck: Mill Neck is a charming village located a mere 1.2km from Oyster Bay, offering a delightful blend of outdoor activities and cultural experiences. It is an idyllic spot for those who enjoy golf, with several well-maintained courses in the vicinity. The area is also home to educational venues and conference facilities, making it suitable for both leisure and business travellers. Nature enthusiasts can explore scenic parks and enjoy the tranquil atmosphere, while cultural attractions add a unique charm to the experience.
  • Upper Brookville: Upper Brookville is a picturesque village close to Oyster Bay, ideal for families and those seeking urban entertainment. The area boasts a lively shopping precinct, where visitors can browse boutiques and local shops. Music concerts and a nearby water park make for enjoyable family outings. The modern square serves as a social hub, providing a vibrant atmosphere for both residents and visitors alike. With its blend of recreational activities and community spirit, Upper Brookville is perfect for a fun-filled day out.
  • Oyster Bay Cove: Nestled near Oyster Bay, Oyster Bay Cove is a quaint village known for its outdoor offerings and family-friendly environment. Visitors can indulge in golf at local courses or take a refreshing dip at the aquatic centre. The area features beautiful beaches and urban parks that are ideal for relaxation and family picnics. With its combination of recreational spaces and community amenities, Oyster Bay Cove provides a serene yet engaging retreat for tourists looking to unwind and connect with nature.

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.

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 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

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

If you're travelling with a group, family, pets, or seeking longer stays, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oyster Bay with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can filter for all of these options and more on Vrbo.
  • Traveling to Oyster Bay with young kids: Travelling with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with ensuring access to age-appropriate facilities, 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 holiday isn’t truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these 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 rentals that offer special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and benefit from savings on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient area for you to plan new adventures, refine your arrangements, or manage your reservations. Your saved or booked properties are now categorised into Potential, Upcoming, or Current Trips for easier access. To discover the Trip Boards, please visit: https://www.vrbo.com/en-gb/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)
  • Oyster Bay Golf Course (4.6 mi / 7.4 km)
  • Harbor Links Golf Course (7.8 mi / 12.6 km)
  • Bethpage Black State Park Golf Course (9.8 mi / 15.8 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:

  • Planting Fields Arboretum State Historic Park (1.6 mi / 2.5 km)
  • Cold Spring Harbor State Park (3.8 mi / 6.2 km)
  • Cantiague Park (7 mi / 11.3 km)
  • Old Westbury Gardens (7.7 mi / 12.4 km)
  • Huntington Beach (8.1 mi / 13 km)
  • Centerport Beach (8.1 mi / 13.1 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 rental?
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 Vrbo, 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 rental accommodation in Oyster Bay?
Houses are the most popular type of holiday rental in Oyster Bay, according to our data. Even if you have a different vision in mind, Vrbo 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 rental in Oyster Bay?
Different things determine the price of a holiday rental 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 rental 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 Vrbo 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 rental amenities in Oyster Bay?
Some of the most popular rental 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, Vrbo 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 rentals 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 Vrbo and stay connected on your holiday.
How old do you have to be to rent a holiday rental in Oyster Bay?
Age restrictions can vary across properties on Vrbo, 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 rental in Oyster Bay for?
The length of time you can rent a holiday rental 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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