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Greenport West holiday lettings

We found 1,242 holiday rentals — enter your dates for availability

Select from 46 homes, 11 cottages and other holiday rentals in Greenport West to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and air conditioning. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Greenport West

Showing deals for:22 May - 29 May

Image gallery for Summer 2026 Now Available! Grab an Amazing Property in the Heart of the Hamptons

Pool
10 out of 10, Exceptional, (90 reviews)
Exceptional
(90 reviews)

Summer 2026 Now Available! Grab an Amazing Property in the Heart of the Hamptons

Sag Harbor

5% off
Price is £14,457
for 7 nights, 1 home
£2,065 per night
includes taxes & fees
Summer 2026 Now Available! Grab an Amazing Property in the Heart of the Hamptons

Find spaces that suit your style

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Greenport West getaway

Learn about the unique charm of Greenport West with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Greenport West

Are you hoping to find attractions to visit in the area? Venture out of your cosy holiday rental and check out everything that makes Greenport West a one-of-a-kind holiday spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Kontokosta Winery (1.9 mi / 3.1 km)
  • Sannino's Bella Vita Vineyard (5 mi / 8.1 km)
  • Raphael Winery (5.6 mi / 9 km)
  • Pindar Vineyards (5.9 mi / 9.5 km)
  • Bedell Cellars (6.1 mi / 9.9 km)
  • Peconic Bay Winery (7.1 mi / 11.4 km)

Exploring the natural landscape of Greenport West

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Greenport West is a great place to spend some time outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Crescent Beach (1.7 mi / 2.8 km)
  • Sunset Beach (1.7 mi / 2.8 km)
  • 67 Steps Beach (2.1 mi / 3.3 km)
  • Shell Beach (4.2 mi / 6.7 km)
  • Orient Point County Park (8.9 mi / 14.4 km)
  • The Hamptons Beaches (12.4 mi / 20 km)

Travelling to and around Greenport West

The nearest airport is in East Hampton, NY (HTO), located 11.7 mi (18.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Fishers Island, NY (FID-Elizabeth Field), which is 21.7 mi (34.8 km) away.

Frequently asked questions

What is the best area to stay in Greenport West when booking a holiday rental?
When considering a holiday rental in Greenport West, New York, a delightful area to stay is near the waterfront, where you'll find a charming mix of quaint shops and eateries. This location offers easy access to stunning views of the harbour and is ideal for those looking to enjoy the maritime atmosphere.

One of the top attractions in this area is the historic Greenport Village, known for its picturesque streets and vibrant community spirit. Here, you can explore local boutiques, art galleries, and enjoy a meal at one of the delightful seafood restaurants that showcase the region's maritime heritage. Additionally, the nearby Long Island Maritime Museum offers fascinating insights into the area's nautical history, making it a great spot for families or history enthusiasts.

In terms of accommodation, the waterfront area has a variety of properties, ranging from charming cottages to modern apartments, ensuring that visitors can find something that suits their needs.
How much does it cost to rent a holiday home in Greenport West?
Prices for holiday rentals in Greenport West vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Greenport West to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Greenport West holiday house rentals?
You can find great discounts on house rentals in Greenport West on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay holiday rentals in Greenport West?
A long-stay holiday rental in Greenport West is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Greenport West holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Greenport West with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
How early should I book a Greenport West holiday rental?
Book your Greenport West holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Greenport West?
In Greenport West, visitors can enjoy a selection of charming attractions that highlight the area's maritime heritage and natural beauty. The Greenport Village Historic District features beautifully preserved 19th-century buildings and offers a pleasant stroll with boutique shops, art galleries, and restaurants showcasing local seafood.

Nearby, the waterfront offers stunning views and opportunities for boating, fishing, and enjoying the fresh sea air. The Greenport Harbor Brewing Co. provides a local craft beer experience, and its outdoor space is superb for relaxing with a drink.

For those interested in history, the East End Seaport Museum offers insights into the region's maritime past, complete with exhibits and a lighthouse.
Can I change or cancel my Greenport West home rental booking on Vrbo?
To find Greenport West holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Greenport West holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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