Discover Your Perfect The Heights Vacation Homes

Best Vacation Homes in The Heights

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The Heights Pet Friendly Vacation Rentals

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The Heights Large Vacation Homes

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Why Choose Rent By Owner for your The Heights 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 The Heights

When should you plan your Vacation Rentals stay?

Timing your visit to this charming destination can significantly enhance your experience, so consider planning your stay during the region’s most favorable seasons for a relaxing and memorable getaway.

Peak Season Highlights

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Summer (June to August)

During the summer months, this destination experiences warm weather ideal for enjoying outdoor activities and tranquil beach days.

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

The early fall offers pleasant temperatures and fewer crowds, making it a great time to explore and relax in this region.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F

Off-Season Highlights

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Late Fall to Early Winter (November to December)

As the region transitions into winter, cooler temperatures and quieter surroundings provide a peaceful retreat for those seeking solitude.

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

During these colder months, the area is less crowded, offering a serene environment for visitors interested in off-season tranquility.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for The Heights

How to Book Your The Heights 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 The Heights

More Top-Rated Vacation Rentals in The Heights 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 areas perfect for al fresco meals in the region’s scenic setting.
  • Relax on spacious patios or decks that provide ample space for lounging and entertaining.
  • Take advantage of private yards or gardens, ideal for outdoor activities or quiet relaxation.
  • Make use of outdoor grills or barbecue facilities to prepare delicious meals amidst nature.
  • Benefit from access to well-maintained outdoor furniture designed for comfort and convenience.
  • Experience peaceful evenings with outdoor lighting fixtures that enhance the ambiance after sunset.
  • Explore landscaped pathways or outdoor spaces that add charm to your stay here in the region.

Top Attractions Around The Heights

What attractions are nearby?

Here, you can explore nearby boating, fishing, and scenic outdoor activities that showcase the natural beauty of Shelter Island Heights, making it an ideal spot for relaxing escapes and outdoor adventures.

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Family Activities

  • Shelter Island Maritime Museum: Discover maritime history and enjoy interactive exhibits that are perfect for family curiosity in this coastal area.
  • Clamming and Shellfishing Tours: Engage your family in a fun and educational experience by exploring local shellfishing activities unique to the region.
  • Silver Beach: Relax and play on the sandy shores of Silver Beach, offering safe swimming and picnicking options suitable for all ages.
  • Island's Nature Trails: Explore scenic hiking and biking trails around here, providing opportunities to spot local wildlife and enjoy outdoor adventures with your family.
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Adult Activities

  • Beachcombing and Waterfront Walks: Explore the scenic shoreline along Shelter Island by taking leisurely walks and discovering unique seashells, perfect for relaxing after booking your stay here.
  • Yachting and Boating Experiences: Enjoy the region’s maritime charm by renting a boat or joining a guided charter to appreciate the area's picturesque harbor views and vibrant boating culture.
  • Visit Local Art Galleries and Studios: Immerse yourself in the area's creative scene through visits to local galleries showcasing regional artists, offering a cultural escape during your vacation.
  • Golfing at Premier Courses: Tee off at nearby golf courses that blend challenging play with stunning natural surroundings, ideal for a day of leisure in the region.

Other Places to Stay in The Heights, NY

Shelter Island Country Club
Shelter Island Country Club Vacation Rentals
More Places to Stay Near The Heights

The Heights Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the region’s charming eateries to enjoy authentic cuisine and support local businesses during your stay.
  • Visit Nearby Natural Attractions: Make time to discover the area’s scenic parks and waterfronts for relaxing outdoor activities and picturesque views.
  • Plan Excursions in Advance: Book guided tours or boat trips early to ensure availability and maximize your experience here in this destination.
  • Utilize Local Resources: Connect with the community or your vacation rental host for insider tips on hidden gems and events happening during your visit.

Transportation Options

  • Ferry Services: You can enjoy scenic ferry rides connecting the area to nearby islands and mainland, offering a relaxing way to start your visit.
  • Rental Cars: Numerous local agencies provide rental cars, giving you the flexibility to explore the region at your own pace.
  • Taxi and Ride-Sharing: Taxis and ride-sharing services are widely available here, allowing for convenient transportation around Shelter Island Heights and beyond.
  • Bicycle Rentals: Biking is a popular option in this destination, with bike rentals readily accessible for exploring scenic routes along the coast.

Local Customs Options

  • Seafood Dining Etiquette: Locals here take pride in their fresh seafood, and you'll notice that sharing local specialties during meals is a cherished tradition that reflects the community's hospitality.
  • Village Green Celebrations: Participating in seasonal gatherings on the village green offers an authentic way to experience the area's close-knit spirit and appreciation for community events.
  • Historical Preservation Respect: Respect for historic landmarks and architecture is valued, so you’ll find that preserving the area's unique charm is a shared responsibility among residents and visitors alike.
  • Boating Customs: When enjoying the waterways, adhering to local boating regulations and courteous behavior is essential, reflecting the region's strong connection to maritime traditions.

Frequently Asked Questions About The Heights?

1. What are the top vacation rentals in The Heights?

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

2. How many vacation rentals have private pools in The Heights?

There are 100 vacation rentals with private pools near The Heights. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in The Heights are best for families?

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

4. How many Rentbyowner vacation rentals are available in The Heights?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 490 in the The Heights 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 The Heights. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the property owner. It is recommended to review the specific rental listing details or contact the host directly to understand the cancellation terms before booking.

6. Are there any specific check-in and check-out procedures I should be aware of?

Check-in and check-out procedures can differ among properties. You should read the listing description carefully or reach out to the owner for detailed instructions to ensure a smooth arrival and departure experience.

7. Is there parking available at the vacation rentals here?

Parking availability depends on the individual property. Make sure to review the amenities listed or contact the owner for information about parking options during your stay.

8. Do I need to arrange for additional services like cleaning or linens?

Additional services such as cleaning or linens may be offered for an extra fee or included in the rental. Confirm these details when booking by reviewing the listing or discussing with the property owner.

9. What are the rules regarding pets or smoking in the rentals?

Pet and smoking policies vary by property. Check the specific rental listing for restrictions or contact the owner directly to clarify any special requirements to ensure compliance during your stay.

The Heights Top Rated Vacation Rentals

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