Discover Your Perfect Greenport Vacation Homes

Greenport Luxury Rentals

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Greenport Large Vacation Homes

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Why Choose Rent By Owner for your Greenport 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 Greenport Vacation Rentals

Where are the best neighborhoods to stay in Greenport?

When planning your stay in Greenport, New York, choosing the right neighborhood can greatly enhance your vacation experience. Whether you prefer to explore charming waterfront areas or enjoy a more peaceful, residential setting, Greenport offers a variety of neighborhoods suited to different tastes. Each area provides unique access to local attractions and scenic views, making it easy to find the perfect spot for your stay. With reliable and professional vacation rentals available, you can confidently select accommodations that meet your needs while immersing yourself in the inviting atmosphere of Greenport’s diverse neighborhoods.

Pipes Cove

In the peaceful setting of Pipes Cove, you can enjoy a tranquil escape with stunning waterfront views that perfectly complement your stay. This area offers a serene environment ideal for relaxing by the water and experiencing the natural beauty of Greenport.

View 24+ Rentals in Pipes Cove

Best Times to Visit Greenport

When should you plan your Vacation Rentals stay?

Choosing the optimal time to vacation here ensures you experience the best of what this destination has to offer, whether you're seeking a lively summer atmosphere or a peaceful off-season retreat within the region.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this coastal area experiences vibrant activity and warm weather, making it an ideal time to enjoy outdoor pursuits and local events.

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

Early fall offers pleasant weather and a scenic backdrop as the leaves change color, providing a perfect setting for relaxation and exploration here.

Average Temperature Daytime: 70-75°F - Nighttime: mid-50s°F

Off-Season Highlights

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Winter (December to February)

The colder months bring fewer tourists, allowing you to experience a quieter, more peaceful side of the region while enjoying the cozy ambiance.

Average Temperature Daytime: mid-30s°F to low 40s°F - Nighttime: 20-30°F
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Spring (March to May)

Late winter transitioning into early spring provides moderate temperatures and fewer crowds, offering a tranquil environment for exploring this destination's charm.

Average Temperature Daytime: 50-60°F - Nighttime: mid-30s°F to mid-40s°F

Weekly Weather Forecast for Greenport

How to Book Your Greenport 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 Greenport

More Top-Rated Vacation Rentals in Greenport 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 spacious outdoor patio or deck ideal for relaxing or dining al fresco amidst scenic surroundings.
  • Take advantage of a private backyard perfect for activities such as barbecues or outdoor games.
  • Make use of a well-maintained swimming pool to unwind after exploring the local area’s attractions.
  • Benefit from lush landscaped gardens that enhance your outdoor experience and provide tranquil spaces.
  • Utilize amenities like an outdoor fire pit, great for evening gatherings under the stars.
  • Appreciate access to a private dock or waterfront area for boating or fishing excursions.
  • Leverage ample parking space in the driveway or on the property grounds for convenience during your stay.

Top Attractions Around Greenport

What attractions are nearby?

Nearby, you can enjoy a variety of activities such as exploring charming local galleries, strolling along scenic waterfronts, and indulging in fresh regional seafood, all within easy reach of your vacation rentals here in Greenport.

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Family Activities

  • Greenport Maritime Museum: Discover the area's rich maritime history through engaging exhibits and family-friendly activities that bring the region's seafaring heritage to life.
  • North Fork Trolley Tours: Enjoy a nostalgic journey around this seaside destination with guided trolley tours that highlight the area's scenic beauty and local highlights suitable for all ages.
  • Local Art Galleries and Craft Shops: Explore the region’s vibrant arts scene by visiting galleries and boutiques, inspiring creativity and offering family-friendly shopping experiences.
  • Beach Days at Stirling Harbor: Relax and play on the sand at this popular harbor spot, where families can swim, build sandcastles, or simply enjoy the coastal scenery unique to the area.
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Adult Activities

  • Wine Tasting Tours: Explore the local wineries in the region, where you can enjoy tastings and learn about the area's renowned viticulture.
  • Harbor Cruises: Experience scenic boat tours along the waterfront, offering stunning views and a relaxing way to appreciate the area's maritime charm.
  • Artists' Studios and Galleries: Discover the creative spirit by visiting local art galleries and studios, showcasing the region’s vibrant artistic community.
  • Dining at Waterfront Restaurants: Indulge in gourmet meals at seaside eateries that highlight the region's fresh seafood and culinary excellence.

Other Places to Stay in Greenport, NY

Railroad Museum of Long Island
Railroad Museum of Long Island Vacation Rentals
East End Seaport Maritime Museum
East End Seaport Maritime Museum Vacation Rentals
Greenport Carousel
Greenport Carousel Vacation Rentals
Camera Obscura
Camera Obscura Vacation Rentals
Greenport Farmers' Market
Greenport Farmers' Market Vacation Rentals
Norman E. Klipp Marine Park
Norman E. Klipp Marine Park Vacation Rentals
Eastern Long Island Hospital
Eastern Long Island Hospital Vacation Rentals
Stony Brook Eastern Long Island Hospital
Stony Brook Eastern Long Island Hospital Vacation Rentals
Kontokosta Winery
Kontokosta Winery Vacation Rentals
Greenport West
Greenport West Vacation Rentals
Pipes Cove
Pipes Cove Vacation Rentals
More Places to Stay Near Greenport

Greenport Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Cuisine: Take the time to enjoy the region’s renowned seafood and farm-to-table offerings to truly savor your stay.
  • Visit Waterfront Areas: Spend your days by the water, taking advantage of scenic views and tranquil beaches that define this destination’s charm.
  • Plan Leisurely Activities: Make the most of outdoor pursuits like boating or biking to experience the area's natural beauty firsthand.
  • Discover Hidden Gems: Seek out local shops and galleries to get a unique glimpse into the region's vibrant culture and crafts.

Transportation Options

  • Greenport Ferry Service: You can enjoy scenic ferry rides connecting this charming area to nearby destinations, providing a relaxed and picturesque transportation option.
  • Local Taxi and Ride-Sharing Services: Reliable taxi companies and ride-sharing apps offer convenient and quick transportation around the region, ideal for exploring the area from your vacation rental.
  • Car Rentals: Renting a car gives you the flexibility to explore beyond Greenport's downtown, making it easier to reach local attractions and hidden gems in the surrounding region.
  • Bicycle Rentals: For an eco-friendly and leisurely way to discover the area's scenic routes, bicycle rentals are available for your convenience and enjoyment here.

Local Customs Options

  • Seafood Festivals: Partake in the region's renowned seafood festivals to experience local culinary traditions rooted in Greenport's maritime heritage.
  • Boating Etiquette: Embrace the customary boating practices here, which reflect the area's deep connection to its historic shipbuilding and fishing industries.
  • Harbor Greetings: Observe the friendly gestures and greetings among locals at the harbor, showcasing the community’s welcoming spirit in this coastal destination.
  • Farmers’ Market Traditions: Visit the vibrant farmers’ markets to enjoy locally sourced produce, supporting sustainable farm-to-table customs characteristic of this region.

Frequently Asked Questions About Greenport?

1. What are the top vacation rentals in Greenport?

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

2. How many vacation rentals have private pools in Greenport?

There are 23 vacation rentals with private pools near Greenport. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Greenport are best for families?

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

4. How many Rentbyowner vacation rentals are available in Greenport?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 227 in the Greenport 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 Greenport. 

5. What is the cancellation policy for vacation rentals in Greenport, New York?

Cancellation policies vary by property; please review the specific listing details or contact the owner directly to understand the terms and any applicable fees.

6. How do I find available dates for vacation rentals in Greenport, NY?

Availability depends on the property’s calendar; you can check real-time availability by entering your preferred dates on the listing page or contacting the host for assistance.

7. Are there any additional fees or charges when booking a vacation rental here?

Additional fees such as cleaning, service charges, or security deposits are typically outlined in the listing; it’s best to review the property details or reach out to the owner for clarification.

8. What amenities are usually included with vacation rentals in this destination?

Most properties offer essential amenities like Wi-Fi, kitchen facilities, and parking, but specific extras vary—please read the listing description or ask the owner about available amenities.

9. How do I ensure my stay in Greenport meets all safety and health standards?

Property owners adhere to local health guidelines, but for detailed safety measures and cleaning protocols, review the listing information or contact the host directly to confirm standards.

Greenport Top Rated Vacation Rentals

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