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Oyster Bay holiday lettings

We found 1,369 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:16 Jan - 23 Jan

Image gallery for BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Pool
10 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Jericho, NY

16% off
Price is £18,946
for 7 nights, 1 home
£2,707 per night
includes taxes & fees
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

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    Enjoy full kitchens, pools, gardens and more

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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.

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.

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

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.

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)
  • 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 rental?
When considering a holiday rental in Oyster Bay, New York, the most appealing area to stay in is the charming village of Oyster Bay itself. This picturesque neighbourhood is renowned for its beautiful waterfront views and historic charm, making it an ideal spot for visitors seeking both relaxation and exploration. The area boasts a variety of holiday rental properties, ranging from quaint cottages to more contemporary homes, ensuring that you can find the superb accommodation to suit your needs.

One of the top attractions in Oyster Bay is the Theodore Roosevelt Sanctuary and Audubon Centre, a delightful destination for nature lovers and families alike. Here, you can enjoy picturesque trails and the opportunity to observe local wildlife in a serene setting. Another highlight is the Oyster Bay Historical Society, which offers fascinating insights into the rich history of the area, including its connection to the former President Theodore Roosevelt.
How much does it cost to rent a holiday home in Oyster Bay?
Prices for holiday rentals in Oyster Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oyster Bay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oyster Bay holiday house rentals?
You can find great discounts on house rentals in Oyster Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Oyster Bay?
For renting a beach house in Oyster Bay, New York, the area around Oyster Bay Harbour offers stunning waterfront views and a selection of charming holiday rentals. Properties along the shoreline benefit from amenities such as private decks, outdoor dining spaces, and direct access to the sandy beaches, superb for enjoying sunrises over the water. Many of these rentals come equipped with modern kitchens and spacious living areas, making them ideal for families or groups seeking a seaside retreat.

Further along the coast, the area near Theodore Roosevelt Memorial Park is another excellent option. Here, you can find beach houses that often feature large backyards, ideal for barbecues and outdoor games. The proximity to the park also provides opportunities for leisurely strolls and picnics, while the local shops and restaurants in Oyster Bay village add to the convenience for visitors.
What is the most popular type of holiday rental accomodation in Oyster Bay?
In Oyster Bay, holiday houses and apartments are both popular choices, with several of each type available throughout the area. The holiday houses typically feature spacious interiors, multiple bedrooms, and outdoor spaces such as gardens or patios, making them ideal for families or groups looking for a comfortable stay. Many also come with fully equipped kitchens, allowing guests to prepare their own meals. On the other hand, the apartments offer a more compact option and often include amenities like modern kitchens, cosy living areas, and convenient access to local shops and restaurants.
Are there any family house rentals in Oyster Bay?
In Oyster Bay, New York, there are several family-friendly house rentals available, making it an excellent choice for a family getaway. This charming coastal town offers a variety of properties located in neighbourhoods that provide a peaceful atmosphere. Many homes come with spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces that are great for children to play.
Can I rent a holiday home with a pool or hot tub in Oyster Bay?
In Oyster Bay, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque area, located on the North Shore of Long Island, offers a charming coastal atmosphere, making it an attractive destination for travellers. Many of the properties come equipped with private swimming pools, relaxing hot tubs, and outdoor entertaining spaces, great for enjoying the beautiful weather. Amenities such as fully equipped kitchens and spacious living areas are also common, allowing guests to unwind and enjoy their stay comfortably.
Can I find long-stay holiday rentals in Oyster Bay?
A long-stay holiday rental in Oyster Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Oyster Bay?
In Oyster Bay, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come equipped with amenities such as spacious backyards, well-appointed kitchens, and comfortable living areas, making them ideal for families or groups.
Are there any remote work holiday rentals in Oyster Bay?
In Oyster Bay, New York, there are several remote work-friendly holiday rentals available. This charming area, known for its picturesque waterfront and historical significance, offers properties that cater to the needs of those working remotely. Many rentals come equipped with essential amenities such as Wi-Fi, desks, and comfortable seating arrangements, ensuring a productive work environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oyster Bay holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Oyster Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Oyster Bay?
In Oyster Bay, popular rental amenities include modern conveniences that enhance the comfort of guests. Most holiday rentals come equipped with kitchens, allowing travellers to prepare their own meals, alongside essential appliances such as dishwashers and microwaves. Additionally, many properties feature outdoor spaces like patios, where guests can relax and enjoy the fresh air. Coffee makers are also commonly found in the rentals, providing a convenient way to enjoy a warm beverage in the morning.
How early should I book a Oyster Bay holiday rental?
Book your Oyster Bay holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oyster Bay?
In Oyster Bay, visitors can explore a range of attractions that highlight the area's natural beauty and historical significance. The historic Theodore Roosevelt Memorial Park offers scenic waterfront views and walking paths, making it a lovely spot for a leisurely stroll or a picnic. Nearby, the Oyster Bay Historical Society provides insights into the rich history of the area, including exhibits related to Theodore Roosevelt, who frequently visited the town.
Can I change or cancel my Oyster Bay home rental booking on Vrbo?
To find Oyster Bay holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oyster Bay holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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