We found 1,334 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:19 Feb - 26 Feb
Image gallery for The President Mansion
Luxurious Family Retreat - 1.5 Miles to Beach
9.89.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
The President Mansion
Luxurious Family Retreat - 1.5 Miles to Beach
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
Find out more about Oyster Bay
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 Month
Temperature
Precipitation
Cloudiness
Occupancy
Pricing
January
32.5°F (0.3°C)
Light Rain
Mostly Sunny
Average
February
33.8°F (1.0°C)
Light Rain
Mostly Sunny
Average
March
40.3°F (4.6°C)
Light Rain
Mostly Sunny
Average
April
50.2°F (10.1°C)
Light Rain
Mostly Sunny
Average
May
60.1°F (15.6°C)
Light Rain
Mostly Sunny
Slightly Low
June
69.3°F (20.7°C)
Light Rain
Mostly Sunny
Average
July
76.3°F (24.6°C)
Light Rain
Mostly Sunny
Slightly High
August
75.4°F (24.1°C)
Light Rain
Mostly Sunny
Slightly High
September
68.9°F (20.5°C)
Light Rain
Mostly Sunny
Slightly High
October
58.6°F (14.8°C)
Light Rain
Mostly Sunny
Average
November
47.3°F (8.5°C)
Light Rain
Mostly Sunny
Slightly Low
December
39.2°F (4.0°C)
Light Rain
Mostly Sunny
Slightly 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.
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 best area to stay is the charming waterfront neighbourhood. This area offers a delightful mix of scenic beauty and local attractions, making it an ideal choice for visitors. You'll find a variety of properties available, ranging from quaint cottages to more spacious homes, suiting different tastes and budgets.
One of the main attractions in this vicinity is the beautiful Oyster Bay Town Park, where you can enjoy leisurely strolls along the waterfront, picnics, and stunning views of the bay. Additionally, the historic Theodore Roosevelt Estate at Sagamore Hill is just a short distance away, providing an insightful glimpse into the life of the 26th President of the United States, complete with lovely grounds to explore.
Staying in this waterfront neighbourhood not only places you close to these highlights but also immerses you in the local culture and community vibe.
Where are the best areas for renting a beach house in Oyster Bay?
For renting a beach house in Oyster Bay, the area along the scenic Oyster Bay Harbor is an excellent choice. This waterfront location offers stunning views and easy access to sandy beaches, superb for a relaxing getaway. Properties in this vicinity often feature amenities such as spacious outdoor decks, private docks, and expansive gardens, ideal for families or groups looking to enjoy the coastal atmosphere.
The nearby Cove Neck area provides additional options, where charming homes are located among lush greenery and close to the shoreline. Many of these rentals come equipped with modern kitchens, comfortable living areas, and sometimes even amenities like swimming pools or hot tubs, enhancing the holiday experience. The proximity to local parks and nature preserves adds to the appeal, allowing guests to explore the beautiful surroundings.
In addition, the Oyster Bay Town Park offers recreational facilities, including picnic areas and playgrounds, making it a family-friendly destination. Rentals in this area often provide easy access to both the beach and local amenities, with shops and restaurants just a short drive away.
What is the most popular type of holiday rental accomodation in Oyster Bay?
In Oyster Bay, holiday houses are the most popular type of holiday rental, with several available throughout the charming neighbourhood. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios, superb for relaxing after a day of exploring the area's beautiful coastal scenery. Additionally, there are several apartments that provide a more compact option for visitors, often featuring modern amenities like Wi-Fi and laundry facilities.
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 appealing destination for those travelling with children. This charming coastal area offers properties in neighbourhoods that are close to the waterfront and local parks. Many of these homes feature spacious living rooms, fully equipped kitchens for family meals, and outdoor spaces great for kids to play.
Visitors can enjoy nearby attractions such as the beautiful Oyster Bay Town Park, which boasts playgrounds, picnic areas, and scenic walking trails along the shore. Additionally, the historic Theodore Roosevelt Sanctuary and Audubon Centre provides opportunities for nature walks and educational experiences.
Are there any remote work holiday rentals in Oyster Bay?
In Oyster Bay, New York, there are several remote work-friendly holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties come equipped with essential amenities such as free Wi-Fi, comfortable desks, and spaces conducive to productivity. Guests can expect a pleasant working environment within their accommodations, allowing for a seamless blend of work and relaxation.
The charming waterfront area offers a peaceful setting, with opportunities for outdoor activities and exploration. Nearby, visitors can enjoy local parks and the scenic beauty of Oyster Bay, providing a superb backdrop for after-work activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Oyster Bay?
In Oyster Bay, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, as well as coffee and tea makers for a convenient morning routine. Most properties also provide onsite parking, making it easy for travellers to explore the area. Many rentals feature balconies, providing a lovely space to enjoy the fresh air and local views. Additionally, the proximity to nearby beaches enhances the appeal of these accommodations, allowing guests to easily access the sandy shores for relaxation and recreation.
When is the best time to visit Oyster Bay for a holiday rental?
The peak season for visiting Oyster Bay runs from July to September, with July being the most popular month. This vibrant time of year attracts families and leisure seekers eager to enjoy the warm coastal weather, making it ideal for outdoor activities such as beach outings, boating, and exploring local parks.
During these summer months, visitors can relish temperatures typically ranging from the mid-teens to low 30s Celsius, providing a comfortable climate for sightseeing and enjoying the beautiful waterfront views. The lively option is enhanced by various local events and festivals, great for immersing yourself in the community spirit.
For those looking for a more budget-friendly option, November presents a wonderful opportunity to experience Oyster Bay's charm without the crowds. While the weather may be cooler, typically hovering around 5 to 10 degrees Celsius, the tranquil atmosphere is great for enjoying peaceful walks along the shore or visiting quaint shops and eateries.
Ultimately, your ideal visit to Oyster Bay will depend on whether you prefer the bustling energy of summer or the quieter beauty of late autumn.
What are the top attractions in Oyster Bay?
In Oyster Bay, visitors can enjoy a variety of attractions showcasing the area's rich history and natural beauty. The Theodore Roosevelt Sanctuary and Audubon Centre is a highlight, providing opportunities for bird watching and nature walks amidst beautiful scenery. Just a short distance away, the Oyster Bay Historical Society offers insights into the region's past with various exhibits and events.
The charming waterfront area is superb for leisurely strolls, and the nearby Planting Fields Arboretum State Historic Park features stunning gardens and historic buildings, making it a lovely spot for picnics and outdoor activities. For those interested in sailing, the Oyster Bay Harbor provides picturesque views and access to water sports.
Are all fees included in the Oyster Bay holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Oyster Bay holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Oyster Bay holiday homes?
You can find great discounts on holiday homes in Oyster Bay on Bookabach, 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.
Can I change or cancel my Oyster Bay holiday home booking on Bookabach?
To find Oyster Bay holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Oyster Bay?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Oyster Bay holiday home?
Book your Oyster Bay holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.
*Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Oyster Bay?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Oyster Bay to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way.
Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you’re protected and that if something goes wrong, we will do our best to make it right as applicable.
If a significant issue arises that your host can’t resolve, we’ll help you address it, find a similar property, or get your reservation refunded if applicable. That’s our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive.
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