Greenport West holiday rentals

We found 1,230 holiday rentals — enter your dates for availability
Discover a selection of 46 homes and other holiday rentals in Greenport West that are 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:25 Dec - 1 Jan

Exterior
Living area
Dining
Pool
Exceptional
(12 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

8% off
AU$17,057
for 7 nights, 1 room
AU$2,437 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Exterior
Private kitchen
Dining Room
Patio
Exceptional
(103 reviews)

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Sag Harbor

16% off
AU$11,959
for 7 nights, 1 home
AU$1,708 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
view from living room towards pool, outdoor dining
aerial view
living room
kitchen with large island and breakfast table
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
AU$82,247
for 7 nights, 1 home
AU$11,750 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Property grounds
Property grounds
Dining
Kitchen
Exceptional
(17 reviews)

Cornfield Point Cottage

Old Saybrook

8% off
AU$11,507
for 7 nights, 1 home
AU$1,644 per night
includes taxes & fees
Cornfield Point Cottage
Outdoor dining
Pool
Dining Room with seating for Ten
Master bedroom with ensuite bathroom
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
AU$12,100
for 7 nights, 1 home
AU$1,729 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Exterior
Exterior
Pool
Spacious Main Floor Living room
Exceptional
(11 reviews)

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold

8% off
AU$17,656
for 7 nights, 1 home
AU$2,522 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
More vineyard views
Outdoor dining
Living area
Welcome to Vineyard View
Exceptional
(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
AU$9,943
for 7 nights, 1 home
AU$1,420 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Pool
Living area
Interior
Exterior detail
Exceptional
(11 reviews)

Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house

Sag Harbor

8% off
AU$14,475
for 7 nights, 1 cottage
AU$2,068 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Kitchen from dining room
Master bed onto balcony
Hall into sitting room
Dining room from kitchen
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
AU$19,148
for 7 nights, 1 home
AU$2,735 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Interior
Terrace/patio
Private kitchen
Interior
Exceptional
(20 reviews)

Entire, new, roomy, village beach house close to beach, park, and town center

Greenport

8% off
AU$6,716
for 7 nights, 1 home
AU$959 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Private kitchen
Dining
Outdoor dining
Living area
Exceptional
(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off
AU$7,028
for 7 nights, 1 cottage
AU$1,004 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Living area
Terrace/patio
Living area
Exterior
Exceptional
(8 reviews)

North Fork Waterfront Gem

East Marion

6% off
AU$8,055
for 7 nights, 1 home
AU$1,151 per night
includes taxes & fees
North Fork Waterfront Gem
The front porch
A view of the house and pool from the creek, looking south
The front walkway
The kitchen is all glass with a spectacular view of the pool and creek
Exceptional
(21 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
AU$6,246
for 7 nights, 1 home
AU$892 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Attention to details and fine workmanship was a sign of wealth both then and now
Every season brings special flower blooms
Second living room once called the "parlour"
Our porch is furnished with plants for a Gilded Age feel
Exceptional
(37 reviews)

Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

Greenport

12% off
AU$10,958
for 7 nights, 1 home
AU$1,565 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Dining
Private kitchen
Private kitchen
Room
Exceptional
(14 reviews)

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold

8% off
AU$6,493
for 7 nights, 1 home
AU$928 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Room
Kitchen
Exterior
Living Room
Exceptional
(6 reviews)

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

New Suffolk

8% off
AU$4,893
for 7 nights, 1 home
AU$699 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Shed
Kitchen
Bedroom 3, Queen Bed
Living Room
Exceptional
(108 reviews)

Relax in this light-filled home, steps from the beach and a short walk to town!

Greenport

8% off
AU$8,851
for 7 nights, 1 home
AU$1,264 per night
includes taxes & fees
Relax in this light-filled home, steps from the beach and a short walk to town!
Second living room
Wrap around deck
Living room
Second eating area
Exceptional
(34 reviews)

Our Peaceful, Beach Escape From the City

Sag Harbor

8% off
AU$11,623
for 7 nights, 1 home
AU$1,660 per night
includes taxes & fees
Our Peaceful, Beach Escape From the City
Pool
Property grounds
Property grounds
Exterior
Exceptional
(91 reviews)

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport

8% off
AU$4,832
for 7 nights, 1 apartment
AU$690 per night
includes taxes & fees
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Dining
Outdoor dining
Private kitchen
Room
Exceptional
(7 reviews)

Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.

Shelter Island

7% off
AU$1,994
for 7 nights, 1 home
AU$285 per night
includes taxes & fees
Cozy Ranch five minutes from Mashomack Preserve, beaches and miniature golf.
Terrace/patio
Pool
Private kitchen
Room
Exceptional
(11 reviews)

Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport

East Marion

8% off
AU$8,953
for 7 nights, 1 home
AU$1,279 per night
includes taxes & fees
Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport
Sidewalk View #1
Living Room View#1
Living Room View#8
Living Room View#2
Exceptional
(85 reviews)

Whaling Captain Pierson's Cottage

Sag Harbor

8% off
AU$3,960
for 7 nights, 1 cottage
AU$566 per night
includes taxes & fees
Whaling Captain Pierson's Cottage
Interior
Private kitchen
Living area
Dining
Exceptional
(13 reviews)

Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street

Sag Harbor

8% off
AU$20,216
for 7 nights, 1 home
AU$2,888 per night
includes taxes & fees
Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street
Pool
Interior
Exterior
Living area
Exceptional
(11 reviews)

Lovely Private Estate In East Hampton

East Hampton

9% off
AU$7,901
for 7 nights, 1 home
AU$1,129 per night
includes taxes & fees
Lovely Private Estate In East Hampton

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, 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)
  • 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)
  • Wolffer Estates Vineyard (11.8 mi / 18.9 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:

  • Sunset Beach (1.7 mi / 2.8 km)
  • 67 Steps Beach (2.1 mi / 3.3 km)
  • Havens Beach (8.4 mi / 13.5 km)
  • Orient Point County Park (8.9 mi / 14.4 km)
  • The Hamptons Beaches (12.4 mi / 20 km)
  • LongHouse Reserve (12.5 mi / 20.1 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.
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.
Are all fees included in the Greenport West holiday homes prices shown on Stayz?
Stayz 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.
Are there any Greenport West holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Greenport West holiday homes?
You can find great discounts on holiday homes in Greenport West on Stayz, 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 change or cancel my Greenport West holiday home booking on Stayz?
To find Greenport West holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Greenport West?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Greenport West holiday home?
Book your Greenport West holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Greenport West?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Greenport West to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.