Discover Your Perfect Oyster Bay Vacation Homes

Why Choose Rent By Owner for your Oyster Bay Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Oyster Bay

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here ensures you experience the area's natural beauty and local charm at its best, making your search for the perfect vacation rental in Oyster Bay, New York, more enjoyable and rewarding.

Peak Season Highlights

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Summer (June to August)

Experience the warm and lively atmosphere of this destination's summer months, perfect for enjoying outdoor activities and stunning coastal views.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
autumn
Fall (September to November)

Enjoy the vibrant fall foliage and pleasant weather as locals and visitors alike indulge in scenic walks and seasonal events.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

Visit during the winter months when you can experience quieter surroundings and cooler temperatures, ideal for cozy retreats.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 25°F to 35°F
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Spring (March to May)

Witness the region's early spring bloom and enjoy fewer crowds while booking your preferred vacation rentals for a peaceful stay.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Oyster Bay

How to Book Your Oyster Bay Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Oyster Bay

More Top-Rated Vacation Rentals in Oyster Bay Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private backyard with space for outdoor dining and relaxation amidst the scenic surroundings.
  • Take advantage of outdoor barbecue grills to host cookouts in this charming region.
  • Relax on a spacious patio or deck, perfect for soaking up the local atmosphere.
  • Make use of beautifully maintained gardens that add to the outdoor appeal of your stay.
  • Benefit from ample parking areas suitable for exploring the nearby attractions of this coastal destination.
  • Discover outdoor seating areas designed for unwinding while enjoying the serene views of the area.
  • Utilize access to outdoor recreational equipment for activities like kayaking or paddleboarding, if available locally.

Top Attractions Around Oyster Bay

What attractions are nearby?

During your stay here, you'll find a variety of nearby activities to enjoy in the region, including exploring scenic parks, engaging in waterfront recreation, and discovering charming local attractions that showcase the area's natural beauty and cultural heritage.

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Family Activities

  • Oyster Bay Marine Center: You can explore the region's maritime heritage through hands-on exhibits and boat tours suitable for family members of all ages.
  • Bayside Park: Here, you can enjoy a relaxing day outdoors with picnic areas, playgrounds, and scenic waterfront views that are perfect for family outings.
  • The Bayville Adventure Park: This destination offers exciting mini-golf courses and engaging arcade games that ensure fun-filled moments for everyone in your group.
  • Oyster Bay Historical Society: For a bit of educational entertainment, you can visit this local museum to learn about the area's rich history and cultural heritage.
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Adult Activities

  • Explore the Sagamore Hill National Historic Site: Discover the former home of Theodore Roosevelt and immerse yourself in the history and natural beauty that surround this iconic landmark.
  • Enjoy a scenic cruise from Oyster Bay Harbor: Experience the region's coastal charm by taking a boat tour that offers breathtaking views of the shoreline and local wildlife.
  • Visit the Oyster Bay Railroad Museum: Dive into the area's transportation history through engaging exhibits and vintage train displays, perfect for a leisurely afternoon.
  • Stroll through Theodore Roosevelt Sanctuary & Audubon Center: Connect with nature on guided walks and observe local bird species while exploring this peaceful natural reserve near here.

Other Places to Stay in Oyster Bay, NY

Oyster Bay Cove
Oyster Bay Cove Vacation Rentals
Theodore Roosevelt Sanctuary
Theodore Roosevelt Sanctuary Vacation Rentals
Theodore Roosevelt Memorial Park
Theodore Roosevelt Memorial Park Vacation Rentals
20th Century Cycles
20th Century Cycles Vacation Rentals
Cove Neck
Cove Neck Vacation Rentals
Sagamore Hill National Historic Site
Sagamore Hill National Historic Site Vacation Rentals
More Places to Stay Near Oyster Bay

Oyster Bay Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Local Events: Check the area's event calendar to align your stay with seasonal festivals or cultural events, enhancing your experience in this charming destination.
  • Explore Waterfront Activities: Take advantage of the region's scenic waterfront by engaging in boating, fishing, or simply relaxing by the water to immerse yourself in the local vibe.
  • Discover Nearby Dining: Sample the regional cuisine at nearby restaurants or secure some fresh local ingredients for a cozy meal at your vacation rental here.
  • Utilize Local Transportation: Use available transportation options to navigate easily around the area and explore hidden gems without hassle during your stay.

Transportation Options

  • Long Island Rail Road: This commuter rail service offers convenient access to New York City and other parts of Long Island, making it easy for you to explore beyond the area.
  • Driving via Car: With well-maintained highways and scenic routes, traveling by car provides flexibility and comfort as you navigate here and discover local attractions.
  • Local Bus Services: Regional bus networks connect this destination to nearby towns and transportation hubs, offering affordable and reliable options for getting around.
  • Taxis and Rideshare Services: Taxis and apps like Uber or Lyft operate within the region, providing convenient door-to-door transportation when you prefer a hassle-free experience.

Local Customs Options

  • Local Seafood Festivals: Participating in seasonal seafood festivals allows you to experience the region's rich maritime heritage and fresh local catches.
  • Traditional Maritime Customs: Observing fishing practices and boat parades offers insight into the area's historic dependence on the sea.
  • Historic Landmark Celebrations: Engaging in events that honor the area's storied past provides a deeper understanding of its cultural roots.
  • Community Holiday Parades: Celebrating festive occasions with neighborhood parades reflects the friendly and welcoming spirit of this destination.

Frequently Asked Questions About Oyster Bay?

1. What are the top vacation rentals in Oyster Bay?

There are a lot of options in Oyster Bay. If you plan on staying in the Oyster Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oyster Bay:

2. Which vacation homes in Oyster Bay are best for families?

If you are looking for a family-friendly vacation home in Oyster Bay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oyster Bay:

3. How many Rentbyowner vacation rentals are available in Oyster Bay?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 23 in the Oyster Bay area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Oyster Bay. 

4. What is the cancellation policy for vacation rentals in Oyster Bay, New York?

Cancellation policies vary depending on the individual listing. You should review the specific property's cancellation terms before booking or contact the owner directly for clarification.

5. How do I ensure my booking in Oyster Bay is secure and reliable?

To guarantee a safe booking experience, choose listings that are verified and reviewed by previous guests. Communicate through the platform's messaging system and confirm payment methods are protected.

6. Are there any additional fees I should be aware of when booking here?

Additional fees such as cleaning charges, service fees, or local taxes might apply. Details are typically outlined in the property listing, but it’s advisable to review these before confirming your reservation.

7. Can I find pet-friendly vacation rentals in this area?

Yes, there are pet-friendly options available. Check the property description for pet policies and restrictions, and contact the owner if you have specific questions about bringing your pet.

8. What amenities should I expect from vacation rentals in Oyster Bay, New York?

Amenities vary by property, but common features include Wi-Fi, parking, kitchen facilities, and outdoor spaces. Review each listing thoroughly to find accommodations that meet your needs.