House in Greenport, NY
8 guests · 4 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
NO EXTRA FEES FOR CLEANING, EXTRA GUESTS & AMENITIES!
Relax in one of America's most beautiful seaside villages, historic Greenport. Walk to the village and within minutes to vineyards, Lavender farm, golf and beaches also Shelter Island and Orient Point Ferries. Take the Hampton Jitney or LIRR from the city and walk to our breathtaking home.
Elegant and located on Captains Row in the Greenport Historic District. Elegantly built for the wealthiest banker on the North Fork. Largest property in National Historic District in Greenport Village. The backyard is truly special, private with pergola and outdoor grill perfect for dining under the stars and our new giant chess set is sure to please.
Lovingly restored to its original elegance and authentic Classic Queen Anne Victorian. This is a complete modern home with new kitchen and bathrooms. This home has been the subject of many artists!
Enter this home and feel the impeccable carpentry work with its rich patina. Magnificent 5 foot single pocket siding doors that separate the formal rooms glide with your fingertips. Top of the line kitchen appliances. New luxury linens, mattresses and romantic brass and iron beds. Feel the elegance of the bygone era. There is even a small library and doll house room. All lighting is exquisitely original, restored and sets the mood. Any celebrations are to be enjoyed by our overnight renters only.
Please do not plan any events with our property in mind.
Please do not plan to do entertainment cooking here. This is a historic house and we encourage outdoor dining or light meals. Sadly, no frying allowed in our home.
We are compliant with local laws and there are minimum stay requirements.
For special consideration, please email us. Weekend rates apply to holidays.
We will try our best to accommodate you and create a wonderful experience!
Relax in one of America's most beautiful seaside villages, historic Greenport. Walk to the village and within minutes to vineyards, Lavender farm, golf and beaches also Shelter Island and Orient Point Ferries. Take the Hampton Jitney or LIRR from the city and walk to our breathtaking home.
Elegant and located on Captains Row in the Greenport Historic District. Elegantly built for the wealthiest banker on the North Fork. Largest property in National Historic District in Greenport Village. The backyard is truly special, private with pergola and outdoor grill perfect for dining under the stars and our new giant chess set is sure to please.
Lovingly restored to its original elegance and authentic Classic Queen Anne Victorian. This is a complete modern home with new kitchen and bathrooms. This home has been the subject of many artists!
Enter this home and feel the impeccable carpentry work with its rich patina. Magnificent 5 foot single pocket siding doors that separate the formal rooms glide with your fingertips. Top of the line kitchen appliances. New luxury linens, mattresses and romantic brass and iron beds. Feel the elegance of the bygone era. There is even a small library and doll house room. All lighting is exquisitely original, restored and sets the mood. Any celebrations are to be enjoyed by our overnight renters only.
Please do not plan any events with our property in mind.
Please do not plan to do entertainment cooking here. This is a historic house and we encourage outdoor dining or light meals. Sadly, no frying allowed in our home.
We are compliant with local laws and there are minimum stay requirements.
For special consideration, please email us. Weekend rates apply to holidays.
We will try our best to accommodate you and create a wonderful experience!
Amenities at Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Non-smoking
No pets allowed
Family friendly
Map of Greenport, NY
Ratings and reviews
10 / 10Outstanding·Oct 2025
Absolutely spotless and beautiful home!! Great location with lots of restaurant options. Shelter Island was great and the winery as well! We were a group of eight 60 year old college friends. Not one of us had a car and we didn't need one! We were able to walk to all of the great spots. So close to 67 Steps beach which was gorgeous!! Thank you to our wonderful hostess!!
8 / 10Excellent·Jul 2025
The home was beautiful and it really felt like you were living in a part of history. It was an easy and quick walk to town. We really enjoyed our stay there.
10 / 10Outstanding·Sep 2024
This property was the most beautiful and well maintained we have ever rented. It’s roomy and comfortable and just wonderful to stay there. We’d love to stay there again.
5 / 10·Sep 2020
Lovely home and yard, immaculate housekeeping, exquisite historical details with modern appliances. Can walk to town or beach. Would stay again!
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Top rated by guests
10Outstanding
(34 Ratings)
"Absolutely spotless and beautiful home!! Great location with lots of restaurant options. Shelter Island was great and the winery as well! We were a group of eight 60 year old college friends. Not o..."
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