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

Photo gallery for Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

A two-story house with a wrap-around porch, a front staircase, and a well-maintained garden.
A dining area with a round table, chairs, and a television on a side table.
A covered porch with white wicker furniture and green cushions, overlooking a street with houses and trees.
A traditional living room with a fireplace, wooden furniture, and a staircase leading to another level.
A grand staircase with wooden railings and a chandelier, leading to a dining area with a table and chairs.

Reviews

10 out of 10
Exceptional
Set in the city center, this vacation home features 4 bedrooms and 2 bathrooms, accommodating 8 guests. Enjoy activities like sailing, birdwatching, and fishing nearby. Relax on the deck, patio, or balcony while exploring attractions such as Kontokosta Winery and Safe Harbor Stirling, alongside golf for sports enthusiasts.

Highlights

  • The great outdoors

    Guests love the outdoor space here.

  • Garage parking available

    Enjoy the convenience of garage parking - a rare offering in the area.

  • Centrally-located

    You're never far from where you need to be with this convenient location.

  • Discover nearby landmarks

    Near 67 Steps Beach
4 bedrooms2+ bathroomsSleeps 8

Popular amenities

  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Balcony

Explore the area

View map
Greenport, NY
  • Place, Kontokosta Winery
    ‪9 min walk‬
  • Place, Greenport Carousel
    ‪14 min walk‬
  • Place, 67 Steps Beach
    ‪16 min walk‬
  • Airport, New London, CT (GON-Groton - New London)
    ‪139 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 1

1 Queen Bed

Bedroom 1

1 King Bed

Bedroom 1

1 Queen Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet

Bathroom 3

Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Garden
Dining area

About this property

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

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!

Add dates for prices

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House Rules

Check in after 4:00 PM

Check out before 11:00 AM

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Children

Children allowed: ages 0–17

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Events

No events allowed

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Pets

No pets allowed

Pet free home but we would consider case by case

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Smoking

Smoking is not permitted

Non smoking on the premise....but ok outdoors

Please no parties or outside guests. Light cooking as this is a historical home....

Excessive messes made will require an extra cleaning fee of $200. Pictures will be taken after any excessive mess made

Important information

You need to know

Property # 998556vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Greenport

Located in Greenport, this holiday home is in the city centre and by the sea. The Hamptons Beaches and 67 Steps Beach reflect the area's natural beauty and area attractions include Greenport Carousel and East End Seaport Maritime Museum. Travelling with kids? Consider Railroad Museum of Long Island and Norman E. Klipp Marine Park. Jet skiing and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and hiking/biking trails nearby.
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Map
Greenport, NY

What's nearby

  • Kontokosta Winery - 9 min walk - 0.8 km
  • Safe Harbor Stirling - 11 min walk - 1.0 km
  • Greenport Harbor Brewing Company - 13 min walk - 1.1 km
  • Greenport Carousel - 14 min walk - 1.2 km
  • 67 Steps Beach - 16 min walk - 1.4 km

Getting around

  • Greenport Station - 17 min walk
  • East Hampton, NY (HTO) - 63 min drive

Restaurants

  • ‪Claudio’s Waterfront - ‬15 min walk
  • ‪First And South - ‬11 min walk
  • ‪Goldberg’s Famous Bagels - ‬15 min walk
  • ‪Aldo's - ‬13 min walk
  • ‪Lucharitos - ‬14 min walk

Frequently asked questions

Is Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach?

As of 18 September 2026, prices found for a 1-night stay for 2 adults at Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach on 2 October 2026 start from NZ$5,553, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach?

On-site parking is available at the property.

What time is check-in at Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach?

Check-in begins at 4:00 PM.

What time is check-out at Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach?

Checkout is at 11:00 AM.

Where is Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach located?

This family-friendly Greenport holiday home is located by the sea, within a 10-minute walk of Eastern Long Island Hospital, Stony Brook Eastern Long Island Hospital and Kontokosta Winery. Greenport Carousel and 67 Steps Beach are also within 15 minutes. Greenport Station is 17 minutes by foot.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 35 out of 37 reviews
Rating 8 - Good. 2 out of 37 reviews
Rating 6 - Okay. 0 out of 37 reviews
Rating 4 - Poor. 0 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

10/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, location, listing accuracy
Disliked: Check-in, communication
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.
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Home

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.
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Sofia from Victoria Seasons was a stellar host. Check in was a breeze. The house was fully appointed with everything we needed. The house itself was a delight -- beds comfortable, nice TVs to watch the World Cup, great kitchen. So nice to have a home in wonderful Greenport. I will be back! Thanks Sofia!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vaca

Lovely home. Comfortable and fabulous beds and linens.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely spot for a friends reunion

Spacious comfortable and inviting home. Well-stocked everything. Lovely outdoor spaces and gracious hosts.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Phenomenal historic house!

This historic house was everything advertised! Beautifully restored, clean as a whistle and the beds were awesome! We really loved relaxing on the front porch! You can’t go wrong with this house!
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding Weekend

My niece was getting married nearby and this home was perfect for family members to all stay together. We were able to walk to town for breakfast, lunch and dinner. Great spot!
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Greenport house

The house had everything we needed. It was spacious and clean. The whole process was smooth and the communication was fantastic. We enjoyed being able to walk to and from downtown Greenport.
Stayed 2 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

extremely clean and well-equipped house

Host went above and beyond to stock house with essentials, extras, and more (snacks, toiletries, tons of towels, everything you could need)! House was extremely clean -- one of the cleanest homes I've ever stayed in. Yard was perfect. An easy stay.
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

100th Birthday Celebration

This was the perfect Christmas House for our family while celebrating a 100th Family Birthday nearby. This is a beautifully appointed and true to period Victorian. The home is immaculate and incredibly well tended. The hosts were lovely and very responsive. This was a special stay and made more so by the wonderful surroundings and ease to town. We would stay here again.
Stayed 6 nights in Dec 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!!
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Property

Our stay could not have been more enjoyable. Gift basket was a generous surprise. Enjoyed coffee on the front porch in the morning, and wine in the evening. Back yard was quiet and beautiful. We all enjoyed playing with the chess set. Only negative was our stay was too short.
Stayed 3 nights in Jun 2023
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property was lovely & location was good
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Greenport Vacation

Beautiful historic property walkable to all Greenport and easy drive to beaches and vineyards. Everything as described. Owner very easy communication and flexible with our needs.
Stayed 5 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very Nice

The home was beautiful, clean and spacious, the property manager was very responsive and hospitable.
Stayed 2 nights in Aug 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great experience

Location. Clean. Great outdoor space
Stayed 2 nights in Oct 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection

My group had an amazing stay. The house was beautifully decorated and extremely comfortable. The backyard seating and giant chess set were our favorite part of the property. Sofia was very attentive to any questions we had. We'd 100% stay here, again.
Stayed 3 nights in Sep 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding Celebration

From in and out, it was a perfect experience. The hosts were fabulous, greeting us with an incredibly generous basket of treats. The house is wonderful, and my only complaint is not being able to enjoy it enough as we were never around long enough! Return trip is necessary!
Stayed 3 nights in Aug 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful night

We stayed here overnight for a bday celebration. The house was beautiful and clean and everything exactly that was described. Perfect walking distance to town. Everyone had a wonderful night staying here. The host was easy to deal with as well as gracious and left a wonderful basket of yummy treats to welcome us. Would definitely stay again hopefully in summer to really enjoy the weather and views.
Stayed 1 night in Oct 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Historic Home

We are three couples who were looking to get-a-way from the hustle and bustle of daily life. A well appointed house, Victorian Seasons Stirling is very clean, spacious and equipped with everything you possibly need. The house is within walking distance to Greenport village and close to restaurants local wineries. Relaxation was definitely found this weekend, and we highly recommend this property.
Stayed 2 nights in Oct 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing House, Perfect Location

We loved this house so much. Sofia, was excellent to work with and the attention to detail was incredible. From the welcome basket of goodies, to having the house stocked with all the necessities, and being there to answer any questions we had, you couldn’t ask for more! The outside of the house was so inviting. The pergola was our favorite to sit around and hang with friends. The porch was another great spot too, as well as the lounge chairs under the trees. We never wanted to leave. The inside of the house has an updated historic feel and was immaculate and clean, not to mention so many places to sit and relax! The location couldn’t be more perfect. You can walk to a winery, or down to town and shop or eat. The stroll is very safe and is about a half a mile. If you are planning on a visit to Greenport, don’t look any further!! Highly recommend.
Stayed 2 nights in Sep 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Really awesome find in Greenport

Great getaway for Labor day weekend in perfect house. Very historic and beautifully maintained
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house and property

Lovely home and yard, immaculate housekeeping, exquisite historical details with modern appliances. Can walk to town or beach. Would stay again!
Stayed 4 nights in Aug 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stately and Gracious Both Home and Owner

Sophia and Mike are fastidious in the presentation and maintenance of this home. Every item: linens, appliances, cutlery, dishes, and exquisite yet comfortable furniture are five star The porch was dressed in these large plants with white woven containers to match the beautiful porch wicker furniture. An amazing, relaxing and joyful vacation.
Stayed 30 nights in Jul 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Green port

What a great property with fabulous outdoor space and close proximity to town of green port. We loved our stay and the property manager was very helpful.

About the host

Hosted by Sofia

Host profile image

We love restoring historic homes and returning all aspects back to the original period design. Part of the process includes researching the previous owners and documenting the unique property features. Our mission is to share with our friends the bygone periods of elegance and excellent craftsmanship and meld the 21st century to make our home the best out there!

Why they chose this property

This property is the most well preserved home in the area. It was custom built by the wealthiest man at the turn of the 1900's. The location is prime, walking distance to all of Greenport shops, restaurants and tours. Many vineyards close by. Rent a bicycle and forget about enjoy the outdoors by visiting the marina and nearby beaches.....

What makes this property unique

Historic district centrally located and within walking distance to LIRR, Hampton Jitney, restaurants, shopping and yoga studio.

Languages:

English, Spanish

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