Discover Your Perfect Shelter Island Vacation Homes

Best Vacation Homes in Shelter Island

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Shelter Island Pet Friendly Vacation Rentals

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Shelter Island Large Vacation Homes

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Why Choose Rent By Owner for your Shelter Island 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.

Popular Areas for Shelter Island Vacation Rentals

Where are the best neighborhoods to stay in Shelter Island?

When planning your stay in Shelter Island, exploring different neighborhoods can help you find the perfect setting for your getaway. Each area offers its own unique charm and tranquility, making it easy to tailor your experience to your preferences. Whether you're seeking serene waterfront views or a more central location with convenient access to local amenities, Shelter Island’s diverse neighborhoods provide ideal options for memorable vacation rentals. Trust in a seamless booking experience as you choose the perfect neighborhood to enjoy all that Shelter Island has to offer during your relaxing retreat.

Shorewood

This charming neighborhood offers a peaceful setting with scenic views, making it an ideal choice for those seeking a tranquil escape on Shelter Island. Here, you can enjoy easy access to the waterfront while exploring the region’s natural beauty.

View 182+ Rentals in Shorewood

Coecles Harbor

Perched along the harbor, this area provides a picturesque backdrop for your stay, perfect for relaxing by the water or indulging in local maritime scenery. It’s an excellent base for exploring Shelter Island’s coastal charm.

View 293+ Rentals in Coecles Harbor

MeNonetic Creek

Known for its serene creekside setting, this neighborhood offers a quiet retreat immersed in nature, ideal for travelers looking to unwind and enjoy the region’s tranquil waterways.

View 213+ Rentals in MeNonetic Creek

Montclair Colony

Nestled in a lush, community-focused area, this neighborhood provides a cozy atmosphere close to Shelter Island’s scenic spots, making it perfect for those wanting a peaceful yet accessible stay.

View 197+ Rentals in Montclair Colony

The Heights

Offering elevated views and convenient access to local attractions, this neighborhood suits travelers seeking a combination of panoramic scenery and proximity to Shelter Island’s amenities.

View 419+ Rentals in The Heights

Best Times to Visit Shelter Island

When should you plan your Vacation Rentals stay?

Choosing the ideal time to vacation here can greatly enhance your experience, as seasonal variations in this region influence everything from weather to local events, helping you plan your stay in the most enjoyable and memorable way.

Peak Season Highlights

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Summer (June to August)

During the summer months, this destination experiences warm weather ideal for outdoor activities and exploring the scenic coastline.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 65°F to 70°F
autumn
Early Fall (September to October)

The early fall offers comfortable temperatures and vibrant foliage, making it a perfect time to enjoy the region's natural beauty.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 60°F

Off-Season Highlights

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Late Fall (November to December)

Visit during late fall when the area is quieter, and the cooler weather provides a peaceful atmosphere for relaxing stays.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 45°F
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Winter (January to February)

The winter season brings a serene setting with fewer visitors, offering a tranquil retreat away from the crowds.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 25°F to 30°F

Weekly Weather Forecast for Shelter Island

How to Book Your Shelter Island 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 Shelter Island

More Top-Rated Vacation Rentals in Shelter Island 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 outdoor dining with a fully equipped barbecue grill setup, perfect for gatherings in the area’s scenic surroundings.
  • Relax on spacious patios or decks that offer picturesque views of Shelter Island’s natural beauty.
  • Take advantage of private gardens or lawns ideal for outdoor games and family activities.
  • Make use of a swimming pool or hot tub to unwind while enjoying the peaceful outdoors.
  • Utilize outdoor fireplaces or fire pits for cozy evenings under the stars in this charming region.
  • Benefit from ample parking and easy access to outdoor recreational facilities nearby.
  • Explore expansive yards or wooded areas perfect for nature walks and birdwatching in this tranquil destination.

Top Attractions Around Shelter Island

What attractions are nearby?

Within this scenic region, you can enjoy a variety of outdoor activities such as boating, fishing, and kayaking, all easily accessible from your Shelter Island vacation rentals for a relaxing and active getaway.

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Family Activities

  • Shelter Island Kayaking Adventures: Explore the calm waters surrounding this scenic area by kayak, offering fun and safe paddling experiences for families of all ages.
  • Island Nature Trails: Discover the region’s natural beauty on family-friendly hiking trails that showcase lush landscapes and offer educational wildlife viewing opportunities.
  • Local Beaches and Swimming Spots: Relax and enjoy quality time at the pristine beaches where you can sunbathe, build sandcastles, or take refreshing swims in protected waters.
  • Fishing Excursions: Engage in a family-friendly fishing adventure along the coast, providing both entertainment and the chance to catch local fish species in a tranquil setting.
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Adult Activities

  • Kayaking and Paddleboarding: Explore the calm waters surrounding Shelter Island by renting a kayak or paddleboard to enjoy scenic views and serene nature experiences.
  • Bird Watching and Nature Walks: Discover diverse bird species and native flora along well-maintained trails, making it perfect for nature enthusiasts seeking tranquility here.
  • Fishing Excursions: Take advantage of the area's abundant waterways for a relaxing day of fishing, whether from the shore or on a private boat charter.
  • Wine Tasting Tours: Visit local wineries and tasting rooms to savor regional wines and learn about the area’s viticulture heritage during your stay.

Other Places to Stay in Shelter Island, NY

Sylvester Manor
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Shelter Island Kayak
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Shelter Island Historical Society
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Havens House
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Menantic Creek
Menantic Creek Vacation Rentals
Shorewood
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Wades Beach
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Mashomack Preserve
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Shelter Island Heights
Shelter Island Heights Vacation Rentals
More Places to Stay Near Shelter Island

Shelter Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities in Advance: To make the most of your stay here, consider scheduling outdoor excursions and local dining experiences ahead of time to ensure you capture the best this destination has to offer.
  • Explore the Natural Beauty: Take advantage of the region's scenic spots and tranquil beaches to enjoy relaxing moments immersed in the area’s picturesque environment.
  • Embrace Local Culture: Engage with the community by visiting local shops and markets, enriching your visit with authentic regional flavors and crafts.
  • Select Well-Located Vacation Rentals: Choose accommodations that are conveniently situated to access the area's top attractions and outdoor activities for a seamless experience during your stay.

Transportation Options

  • Ferry Services: You can take a scenic ferry ride connecting Shelter Island with nearby Long Island or other coastal destinations, offering a picturesque start to your getaway.
  • Private Boat Rentals: For a flexible and personalized experience, renting a boat allows you to explore the area's beautiful waterways at your own pace.
  • Taxi and Rideshare Services: Local taxi companies and rideshare options provide convenient transportation for getting around the region efficiently and comfortably.
  • Car Rentals: Renting a vehicle on-island offers the freedom to visit various attractions and enjoy the natural scenery at your convenience.

Local Customs Options

  • Respect for Water-based Traditions: Locals in this region take pride in their maritime heritage, often engaging in and honoring traditional boating and fishing practices.
  • Celebration of Seasonal Events: Participating in seasonal festivals, especially those celebrating local harvests and waterfront activities, is a cherished custom here.
  • Community-Driven Gatherings: The area values close-knit community events where residents gather to celebrate and preserve local customs and traditions.
  • Emphasis on Environmental Stewardship: There is a strong emphasis on respecting the natural landscape through conservation efforts and eco-friendly practices encouraged by locals.

Frequently Asked Questions About Shelter Island?

1. What are the top vacation rentals in Shelter Island?

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

2. How many vacation rentals have private pools in Shelter Island?

There are 21 vacation rentals with private pools near Shelter Island. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Shelter Island are best for families?

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

4. How many Rentbyowner vacation rentals are available in Shelter Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 146 in the Shelter Island 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 Shelter Island. 

5. What is the cancellation policy for vacation rentals in Shelter Island?

Cancellation policies vary by listing, so it’s important to review the specific terms outlined on the property’s page. You can also contact the host directly for detailed information regarding refunds and cancellation deadlines.

6. How do I find available dates and book a vacation rental here?

To confirm availability and secure your reservation, use the search feature on the listing page, select your desired dates, and follow the booking instructions. It's advisable to book early, especially during peak seasons in this destination.

7. Are there any additional fees or deposits required when booking vacation rentals in the area?

Additional fees such as cleaning charges, security deposits, or service fees may apply depending on the property. These details are specified on each listing, so reviewing them carefully before finalizing your booking is recommended.

8. What amenities should I expect in vacation rentals around Shelter Island?

Most properties offer essential amenities like Wi-Fi, fully equipped kitchens, and outdoor spaces. For specific features, check the listing descriptions and photos to ensure the rental meets your needs.

9. Can I contact the property owner directly if I have questions before booking?

Yes, most listings provide a way to message the property owner. Reaching out can help clarify any concerns about the property, availability, or special requests before completing your reservation.

Shelter Island Top Rated Vacation Rentals

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