Discover Your Ideal Sylvester Manor Vacation Rental for a Memorable Shelter Island Getaway
Discover Your Perfect Sylvester Manor Vacation Homes
Best Vacation Homes in Sylvester Manor
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Why Choose Rent By Owner for your Sylvester Manor Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Sylvester Manor Vacation Rentals
Where are the best neighborhoods to stay in Sylvester Manor?
When planning your stay in Sylvester Manor on Shelter Island, exploring the neighborhood options is essential for experiencing the full charm of the area. This tranquil locale offers a variety of neighborhoods that provide unique atmospheres, whether you're seeking peaceful seclusion or vibrant community settings. Choosing the right neighborhood can enhance your visit, offering easy access to local spots and scenic views. With reliable vacation rentals available, you can enjoy a comfortable and convenient base while discovering all that Shelter Island has to offer.
East Hampton North
This neighborhood offers a peaceful retreat with easy access to the scenic beauty and local charm that make the region a popular destination for visitors seeking relaxation.
View 139+ Rentals in East Hampton NorthAmagansett North
Known for its laid-back atmosphere, this area provides an ideal setting for those wanting to enjoy the natural landscapes and tranquil surroundings of the region.
View 46+ Rentals in Amagansett NorthClearwater Beach
Here, you can experience the serene waters and quiet beaches that appeal to travelers looking for a restful getaway in the area.
View 49+ Rentals in Clearwater BeachBay Point
This neighborhood presents a perfect blend of waterfront views and charming community living, making it a desirable choice for visitors exploring here.
View 465+ Rentals in Bay PointPipes Cove
Offering picturesque coastal scenery, Pipes Cove is favored by those wanting direct access to the water and a peaceful environment.
View 26+ Rentals in Pipes CoveAmagansett Lanes
A quaint area known for its welcoming atmosphere and proximity to local attractions, ideal for travelers seeking convenience and comfort.
View 541+ Rentals in Amagansett LanesBarnes Landing
Situated near the water, this neighborhood provides scenic views and a quiet ambiance, perfect for relaxing retreats in the region.
View 599+ Rentals in Barnes LandingThe Heights
Perched above the harbor, this area offers stunning vistas and a peaceful environment, suitable for those wanting to immerse themselves in the natural beauty of the region.
View 419+ Rentals in The HeightsBest Times to Visit Sylvester Manor
When should you plan your Vacation Rentals stay?
To make the most of your stay here, consider visiting during the shoulder seasons when the region offers pleasant weather and fewer crowds, allowing you to experience Sylvester Manor with a more relaxed and authentic atmosphere.
Peak Season Highlights
June to August
During the summer months, the area experiences its warmest weather, making it ideal for enjoying outdoor activities and scenic views.
September to October
Early fall offers pleasant temperatures and vibrant foliage, drawing visitors seeking a peaceful retreat in this destination.
Off-Season Highlights
November to March
The cooler season sees fewer visitors, providing a tranquil experience in the region and opportunities for quiet exploration.
April to May
Springtime brings mild temperatures and blossoming landscapes, perfect for those seeking a serene getaway outside peak times.
Weekly Weather Forecast for Sylvester Manor
How to Book Your Sylvester Manor Vacation Rental Home
What's our booking process?
Booking Steps
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Explore and book the perfect rental in Sylvester Manor
Common Vacation Rentals Amenities
What amenities can you expect?
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 private barbecue grill and picnic area.
- Relax in the sun on spacious outdoor patios or decks overlooking scenic views.
- Take advantage of a well-maintained swimming pool for leisurely swims in warm weather.
- Benefit from beautifully landscaped gardens perfect for strolling or relaxing outdoors.
- Make use of outdoor sports amenities such as tennis courts or basketball hoops.
- Host gatherings around a cozy fire pit during cool evenings.
- Explore nearby nature trails or hiking paths accessible directly from your rental here.
Top Attractions Around Sylvester Manor
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities, explore scenic beaches, and discover local parks—all just moments from your vacation rental in Sylvester Manor on Shelter Island.

Family Activities
- Shelter Island Historical Museum: Engage with the local history through interactive exhibits that bring the area's past to life for families seeking educational activities.
- Shellfish Farming Tours: Discover the region's maritime heritage by participating in family-friendly tours that showcase sustainable shellfish farming practices here.
- Sunset Beach Activities: Relax and enjoy the scenic shoreline, where families can build sandcastles, dip their toes in the water, or watch stunning sunsets over the bay.
- Nature Walks at Sylvester Manor: Explore the lush grounds and scenic trails surrounding this historic estate, offering a peaceful outdoor adventure suitable for all ages.
Adult Activities
- Guided Nature Walks: Experience the serenity of the region’s natural beauty through guided walks that highlight the area's unique flora and fauna.
- Historical Tours: Discover the rich history and cultural heritage of here by exploring local museums and historic sites nearby.
- Wine Tasting Experiences: Indulge in wine tasting sessions at nearby wineries, allowing you to enjoy the region’s renowned viticulture.
- Waterfront Activities: Engage in kayaking or paddleboarding along the waterfront, immersing yourself in the tranquil waters surrounding the destination.
Sylvester Manor Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Cuisine: Take the opportunity to try the region’s fresh seafood and farm-to-table dishes to truly immerse yourself in the area’s culinary scene.
- Plan Outdoor Activities: Make the most of the tranquil surroundings by scheduling outdoor pursuits like kayaking or relaxing walks along scenic trails.
- Visit Seasonal Events: Check the local calendar for seasonal festivals or markets that offer authentic experiences and a chance to connect with the community.
- Choose Prime Accommodation: Select a well-located vacation rental that allows easy access to the area's natural beauty and attractions, enhancing your overall stay.
Transportation Options
- Ferry Services: The primary way to access this coastal destination is via ferry, offering a scenic and convenient connection from the mainland to Shelter Island.
- Personal Vehicles: Renting a car provides flexibility to explore locally and reach your vacation rental with ease across the area's charming streets.
- Taxi and Rideshare: Taxis and rideshare services operate in the region, offering a reliable transportation option for quick trips around town or to nearby spots.
- Bicycle Rentals: Biking is an eco-friendly and enjoyable way to navigate the quiet roads and picturesque scenery surrounding this beautiful island destination.
Local Customs Options
- Respect for Nature: Locals here cherish the region’s natural beauty, and you’ll find that outdoor etiquette, such as preserving wildlife and maintaining cleanliness, is an important part of daily life.
- Community Gatherings: Participating in local events and festivals showcases the area’s welcoming spirit and preserves its rich traditions, making your stay more authentic.
- Maritime Traditions: The community’s deep connection to boating and fishing is evident, and observing these customs adds a special touch to your experience here.
- Historical Respect: Appreciation for the historical significance of Sylvester Manor encourages visitors to honor local landmarks and engage respectfully with heritage sites.
Frequently Asked Questions About Sylvester Manor?
1. What are the top vacation rentals in Sylvester Manor?
There are a lot of options in Sylvester Manor. If you plan on staying in the Sylvester Manor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Sylvester Manor:
- Private & Spacious Five Room Suite.Steps To Bay Beach and walk to Village.
- Restored Seaport Village Cottage
- Beautiful, quiet, private, short walk to the beach.
- Relax in this light-filled home, steps from the beach and a short walk to town!
- First Floor 1905 Victorian home in the heart of Greenport Village
- Spacious apartment, 3 blocks to downtown and steps to fishing pier.
- Bright Apartment - 1/2 Mi to Greenport Harbor!
- Cottage on Beach front Estate with Dockage .Walk to Village
- 1820 Whaling Captain's Home - A walk to a coffee or cocktail!
- Peaceful and Private Shelter Island Getaway
2. How many Rentbyowner vacation rentals are available in Sylvester Manor?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 426 in the Sylvester Manor 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 Sylvester Manor.
3. What is the cancellation policy for vacation rentals in Sylvester Manor, Shelter Island?
4. How do I find the best available dates for vacation rentals in Shelter Island?
5. Are there any additional fees I should be aware of when booking a rental here?
6. What amenities are usually included with vacation rentals in this area?
7. How can I ensure my stay complies with local regulations when booking a vacation rental in this destination?
Best Vacation Homes in Sylvester Manor
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- Pet Friendly
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- Pet Friendly
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- Pet Friendly
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- Air Conditioner
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- Pet Friendly
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- Pet Friendly
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- TV