
Vacation rentals in Greenport West
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Top-rated vacation rentals in Greenport West
Guests agree: these stays are highly rated for location, cleanliness, and more.

Cozy Farmhouse Retreat in North Fork, NY
A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

2 BR Waterfront Autumn Escape in Wine Country
Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

The Sandpiper
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Designer's Dream - Charming Boathouse
An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

The Greenport Bungalow
Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

River Barn, Sidewalk Stroll into Essex Village
The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Greenport Beach house Mini Resort Spa & Catering
Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

1830 Historic garden wing - walk to it all
This historic Captain's house is located in the heart of beautiful Greenport Village. It dates back to 1830 and has been beautifully renovated preserving its historic detail. It has a huge garden with mature trees, plants and a wonderful gazebo. Once you step outside, you can walk to all the restaurants, bars, shops, the water as well as the Hampton Jitney and the LIRR. It's an ideal yet very quaint location.

Lovely 2-bedroom apartment in a historic home
Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

Greenport Village Rental
Exquisitely renovated traditional style home offers an open concept first floor, expansive rear deck covered by fixed-in-place awning with a meticulously landscaped backyard and outdoor shower. Located on charming 5th avenue in Greenport Village, Mitchell Park, renowned restaurants and the best of what the North Fork has to offer is only a short walk away.

Walk to Vineyards, Beaches, Farms & Town
Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Private Suite in a Greenport Historical Townhouse
Enjoy the Greenport experience at this centrally located, renovated Victorian home. Our place is a few minutes walk into town, where there is a flourishing restaurant and food scene. Lots of shops, cafes to explore too and beaches are a 15 minute walk. Take a boat tour of the harbor from nearby Preston's Dock.
Popular amenities for Greenport West vacation rentals
Other great vacation rentals in Greenport West

Elegant Greenport Victorian -Winter Harbor House-

Designer Home w/ Heated, Salt-Water Pool

Greenport Village Relaxation

Incredible 2 Bedroom Waterfront Cottage!

North Fork Sound Front Home with Pool

Long Island home w/ large pool

Walk to Beach and Greenport Village, Two King Beds

Beach Cottage!
When is the best time to visit Greenport West?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $480 CAD | $498 CAD | $507 CAD | $515 CAD | $593 CAD | $686 CAD | $778 CAD | $809 CAD | $680 CAD | $563 CAD | $544 CAD | $516 CAD |
| Avg. temp | 0 °C | 1 °C | 4 °C | 10 °C | 16 °C | 21 °C | 24 °C | 24 °C | 20 °C | 14 °C | 8 °C | 3 °C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Greenport West?
Greenport West has more than 260 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there Greenport West vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 100 vacation homes with pools in Greenport West, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Greenport West?
Make yourself at home in Greenport West by choosing from our most frequently booked neighborhoods. We have over 530 vacation rentals in Greenport West, over 530 vacation rentals in Dering Harbor, and over 530 vacation rentals in Greenport.
Do apartment rentals in Greenport West have wifi?
Absolutely! We offer over 30 apartment rentals with wifi in Greenport West. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Greenport West have air conditioning?
Absolutely! We offer over 20 condo rentals with air conditioning in Greenport West. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Greenport West?
Four-legged friends are welcome in Greenport West. Choose from more than 100 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Greenport West?
Yes! Work meets play with ease at over 160 vacation rentals in Greenport West featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do condo rentals in Greenport West have free parking?
Absolutely! We offer over 20 condo rentals with free parking in Greenport West. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greenport West have a kitchen?
Absolutely! We offer over 190 house rentals with a kitchen in Greenport West. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Condo Rentals in Greenport West?
Enhance your stay in our Condo Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Greenport West

Total vacation rentals
Explore 320 vacation rentals in Greenport West

Nightly prices starting at
Greenport West vacation rentals start at $151 CAD per night before taxes and fees

Verified guest reviews
Over 14,960 verified reviews to help you choose

Family-friendly vacation rentals
260 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 100 rentals that welcome pets

Vacation rentals with a pool
100 properties feature pools

Rentals with dedicated workspaces
160 properties have a dedicated workspace

Wifi availability
310 of Greenport West vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Greenport West rentals

4.9 Average rating
Greenport West stays are highly rated by guests—averaging 4.9 out of 5!
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