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Oyster Bay vacation rentals

We found 1,283 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Oyster Bay that are perfect for your trip. Vacation rentals offer the amenities you expect for your family, friends, or furry companion, such as parking and a fireplace. You'll be able to choose a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Oyster Bay

Showing deals for:Nov 21 - Nov 28

Image gallery for 3-LEVEL RETRO HOUSE/CLOSE TO BEACH, NYC, STAMFORD, WESTPORT, GREENWICH

Living area
10 out of 10 rating
Exceptional
(14 reviews)

3-LEVEL RETRO HOUSE/CLOSE TO BEACH, NYC, STAMFORD, WESTPORT, GREENWICH

Norwalk, CT

5% off
Price is CA $459
CA $4,318 total
includes taxes & fees
3-LEVEL RETRO HOUSE/CLOSE TO BEACH, NYC, STAMFORD, WESTPORT, GREENWICH

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Find out more about Oyster Bay

Find out more about Oyster Bay

Why visit Oyster Bay

  1. Charming waterfront communities: Experience the picturesque coastal views and inviting beach houses that define Oyster Bay.
  2. Family-friendly activities: Enjoy a range of attractions suitable for all ages, from parks to recreational facilities.
  3. Outdoor adventures: Explore the scenic surroundings with options for hiking, biking, and relaxing at the beach.
  4. Vibrant downtown Stamford: Discover shops and dining options in the nearby bustling downtown area.
  5. Diverse accommodation: Choose from cozy apartments to stylish condos, perfect for any traveler's needs.

Popular types of accommodation in Oyster Bay

Discover the charm of Oyster Bay with a variety of vacation rentals to suit your needs. Whether you prefer a cozy apartment, a private vacation home, or a stylish condo, we have options that cater to every traveller. From beach rentals in the United States to holiday cottages and New York vacation rentals, your perfect getaway awaits. Enjoy the convenience and reassurance of booking with us today!

  • Apartments: The most sought-after option in Oyster Bay, ideal for those looking for a convenient and comfortable stay.
  • Houses: A popular choice for families and groups, offering the comforts of home in a beautiful setting.
  • Condos: A well-liked accommodation type, perfect for those wanting modern amenities and a community feel.
  • Cottages: Quaint and charming, these rentals provide a cozy retreat close to nature.
  • Villas: Luxurious spaces for those seeking a more upscale experience during their vacation.**

Top attractions in Oyster Bay

Oyster Bay, New York, offers a delightful vacation experience for families, outdoor enthusiasts, and city explorers alike. With a variety of attractions including modern colleges, urban parks, and beautiful beaches, visitors can enjoy a perfect blend of relaxation and adventure. Whether you're travelling solo or with loved ones, Oyster Bay has something for everyone, making it an ideal destination for creating lasting memories.

  1. Sagamore Hill National Historic Site: The former summer home of President Theodore Roosevelt, this historic site offers a fascinating glimpse into the life of one of America's most dynamic leaders, set within beautiful grounds that reflect its cultural significance.
  2. Long Island University Post Campus: A vibrant modern university, this campus boasts impressive architecture and lush landscapes, providing an urban feel with a lively atmosphere, perfect for exploring its art galleries and outdoor areas.
  3. Oheka Castle: A magnificent estate exuding romance and culture, Oheka Castle features exquisite gardens and opulent interiors, making it a perfect spot for a leisurely stroll or a memorable photo opportunity.

Things to do recommended for couples

Experience romance in Oyster Bay! Indulge in a couple's treatment at Hand & Stone Massage and Facial Spa, enjoy a fun round at Monster Mini Golf, and savour exquisite wines at Harmony Vineyards. These delightful activities promise unforgettable moments together.

Things to do recommended for families

Families can splash around at the Nassau County Aquatic Center, enjoy sports at Chelsea Piers, or unwind at Bethpage Community Park. Each location offers a unique atmosphere, ensuring a memorable experience for everyone in the family while exploring Oyster Bay.

Things to do recommended for groups

Groups visiting Oyster Bay can enjoy a captivating show at the nearby Paramount Theater, shop at Roosevelt Field Mall for great family entertainment, or challenge themselves on the Bethpage Black State Park Golf Course, perfect for outdoor sports enthusiasts.

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

If you're travelling with a group, family, or pets, or if you're considering an extended stay, it's important to refine your search based on your key 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 space for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Oyster Bay with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with 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 isn’t truly complete without their furry companion by their side. If this resonates with you, consider exploring 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 vacation rentals offering discounts 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 even a private pool in your search criteria.

Where to stay in Oyster Bay

Oyster Bay, New York, offers a delightful blend of outdoor adventures and family-friendly experiences. With its charming waterfront communities and scenic beach houses, visitors can enjoy relaxing beach getaways. Nearby Stamford boasts a vibrant downtown, perfect for exploring shops and dining. Whether you’re seeking romantic spots or budget-friendly options, Oyster Bay promises a warm atmosphere with friendly locals and stunning water views, making it an ideal destination for a memorable vacation.

  • Mill Neck: Situated just 3.2km from Oyster Bay, Mill Neck is a charming city that offers a delightful blend of outdoor activities, cultural experiences, and business opportunities. This picturesque area is renowned for its scenic golf courses, making it an ideal spot for golf enthusiasts. Visitors can also explore various educational venues and conference centers that host a range of events. Mill Neck’s serene environment and beautiful landscapes provide a peaceful getaway, with local landmarks such as event venues and stadiums enhancing its appeal.
  • Upper Brookville: Nestled within the Oyster Bay area, Upper Brookville is a quaint village known for its family-friendly atmosphere and vibrant entertainment scene. The village boasts a variety of shopping areas that cater to all tastes, along with music concerts that fill the air with a lively spirit. A visit to the local water park is a must for families looking to cool off and have fun together. The modern square and tourist precinct in Upper Brookville offer a great place to unwind and enjoy the community’s charm.
  • Oyster Bay Cove: Also located in the Oyster Bay vicinity, Oyster Bay Cove is a serene village that invites families and outdoor enthusiasts alike. Known for its beautiful golf courses and music concerts, this area offers a range of recreational activities. Visitors can enjoy the nearby beach and family-friendly parks, making it a perfect destination for a relaxing day outdoors. The village's combination of natural beauty and community spirit makes it a delightful stop on your vacation.

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 Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate quite a bit. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can start new trip plans, continue from where you paused, or keep track of your existing itineraries. Your saved or booked properties will be neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The charming city of Oyster Bay awaits you

Experience the unique character of Oyster Bay with a stay in a vacation home rental. Travelers to this romantic city praise the horseback riding, shopping and restaurants. Bronx Zoo and Citi Field are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Oyster Bay

Are you hoping to discover things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Oyster Bay has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 active traveler or just want to appreciate the scenery, Oyster Bay is a great spot to appreciate mother nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Cantiague Park (7 mi / 11.3 km)
  • Old Westbury Gardens (7.7 mi / 12.4 km)
  • Huntington Beach (8.1 mi / 13 km)

Transportation 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 center. If you can't find a flight that's convenient for your trip, you can also fly into Westchester County Airport (HPN), which is 16.3 mi (26.2 km) away.

If you'd rather 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 vacation rental?
When considering a vacation rental in Oyster Bay, New York, a popular area to stay is the charming neighbourhood of Oyster Bay Cove. This picturesque enclave offers a serene atmosphere with stunning waterfront views and lush greenery, making it an ideal retreat. You can immerse yourself in the natural beauty of the area while being conveniently located near attractions such as the Planting Fields Arboretum State Historic Park, where you can explore beautifully landscaped gardens and historic buildings.

Another excellent choice is the quaint village of Oyster Bay itself, which boasts a delightful mix of boutique shops, cafes, and restaurants. This area is particularly appealing for those wanting to experience local culture and community. The Oyster Bay Historical Society is a must-visit for history enthusiasts, offering insights into the region's rich past. In general, Oyster Bay boasts a variety of vacation rental properties, ranging from charming cottages to more spacious homes, providing ample choices to suit different preferences and group sizes.
How much does it cost to rent a vacation home in Oyster Bay?
Prices for vacation 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 travelling 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.
Are there any discounts for Oyster Bay vacation 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, consider the picturesque waterfront areas along the North Shore of Long Island. The vicinity around Oyster Bay Harbor offers charming properties with stunning views of the water, often featuring amenities such as private decks, outdoor dining spaces, and direct access to the beach. Many of these rentals come equipped with modern kitchens and spacious living areas, ideal for families or groups looking to enjoy a relaxing seaside getaway.

Nearby, the area around Planting Fields Arboretum State Historic Park provides a lovely backdrop for beach house rentals. Properties here may include landscaped gardens, outdoor pools, and proximity to walking trails, allowing guests to immerse themselves in the natural beauty of the region. Additionally, the local community offers convenience with shops, cafes, and restaurants, making it easy to enjoy both beach life and local culture.
What is the most popular type of vacation rental accomodation in Oyster Bay?
In Oyster Bay, vacation houses are a popular choice, with several available in the area. These residences typically offer spacious living arrangements, including multiple bedrooms and outdoor spaces, making them ideal for families or groups seeking a comfortable getaway. Many of these houses also feature fully equipped kitchens and cosy living areas, allowing guests to enjoy a cozy feel during their stay.
Are there any family house rentals in Oyster Bay?
In Oyster Bay, New York, there are several family-friendly rentals available. This charming coastal town offers a variety of homes suitable for families, particularly in neighbourhoods like Cove Neck and Oyster Bay Village. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.
Can I rent a vacation home with a pool or hot tub in Oyster Bay?
In Oyster Bay, there are several vacation homes available for rent that feature pools or hot tubs, making it a delightful choice for travellers seeking relaxation and leisure. This picturesque area, located on the North Shore of Long Island, offers a blend of natural beauty and charming local attractions. Many of the properties come with private pools, inviting hot tubs, and well-appointed outdoor spaces, superb for enjoying warm summer days or unwinding after a long day of exploring.
Can I find long-stay vacation rentals in Oyster Bay?
A long-stay vacation 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 furry companions. Many of these vacation homes come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces, ideal for enjoying the beautiful surroundings.
Are there any remote work vacation rentals in Oyster Bay?
In Oyster Bay, New York, there are several remote work vacation rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties are equipped with essential amenities such as Wi-Fi, desks, and comfortable chairs, providing a conducive environment for productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oyster Bay vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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.
When is the best time to visit Oyster Bay for a vacation rental?
The best time to visit Oyster Bay for a vacation rental is during the peak season from July to September. This vibrant period attracts families and adventure seekers eager to enjoy the beautiful beaches and outdoor activities that the area has to offer. With warm temperatures averaging around 27°C, visitors can enjoy sun-soaked days filled with swimming, sailing, and exploring the picturesque waterfront.

July stands out as the most popular month, bustling with activity and a lively atmosphere. It's an ideal time to take advantage of local events, including farmers' markets and festivals that celebrate the region's rich heritage. The pleasant weather makes it great for leisurely strolls along the scenic Oyster Bay waterfront or enjoying a picnic in one of the many nearby parks.

For those looking to save a bit, November presents a wonderful opportunity to visit when the crowds have thinned. While the weather cools down to around 10°C, you can still appreciate the charming coastal scenery and perhaps indulge in some early vacation shopping at local boutiques without the hustle and bustle of peak season.
How early should I book a Oyster Bay vacation rental?
Book your Oyster Bay vacation 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 vacation 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 enjoy a range of attractions that highlight the area's natural beauty and historical significance. The scenic Oyster Bay Town Park offers lovely waterfront views and picnic areas, superb for a relaxing day outdoors. Nearby, the historic Raynham Hall Museum provides insight into the Revolutionary War era, showcasing period furnishings and intriguing exhibits.

For those interested in maritime activities, the Oyster Bay Harbor is a great spot for boating and fishing. The charming downtown area features quaint shops and eateries, making it an enjoyable place to explore. Additionally, the nearby Sagamore Hill National Historic Site, once the home of President Theodore Roosevelt, offers tours of the house and beautiful grounds, enriching the visitor experience with a touch of history.
Can I change or cancel my Oyster Bay home rental booking on Vrbo?
To find Oyster Bay vacation 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 vacation 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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