Updated on Jul 20, 2026
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Type
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Private vacation home
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Bedrooms
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3
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Bathrooms
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2
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House Rules
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Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total);Garden fenced in. Dogs must be walked off premise.
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Children allowed: ages 0-17
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Smoking is not permitted;Smoking outside only.
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No events allowed
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Max Occupancy
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5
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Host Language
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English
Spanish
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Property Id
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3767758
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Set in the historic section of Greenport village, the Captain’s House, built in 1820, is an elegant and charming 3 bedroom, 2 bath home ready to enjoy, especially for a summer getaway or a cozy holiday retreat. It's a 3 block walk into town and a short bike ride or drive to all the area beaches, wineries and treasure finding.
The Captain’s House is in the perfect location for those who’d like to leave the car at home and wander into town to visit shops, wine bars and restaurants. It's even a 10 minute walk from or the Jitney/train.
There are three bedrooms (one with a queen bed, one with 2 twins or king and a smaller 3rd bedroom with a full bed) and two full bathrooms, one with a washer/dryer that is on the ground floor. There are two comfortable living rooms, one with a fireplace and large color TV with Netflix, Amazon Prime, Smart TV as well as a selection of puzzles and board games for all ages. There is a TV in the master bedroom as well. Attached to the living room is a formal dining room with a farm table that seats 8 for those chilly or hot evenings better spent inside.
For the ultimate chef, the home has a fully stocked kitchen with Cuisinart appliances, a Garland stove, every utensil imaginable as well as all dining-ware. There is no need to bring sheets, towels or beach towels, it’s all here. For those with small children, note that I do not toddler-proof the house, remove the nicknacks, etc. so keep that in mind when renting!
There is a very large and beautifully landscaped backyard complete with a 'Secret Garden" hidden in the far back of the property overlooking a zen fountain. Attached to the house is a back deck with a charcoal and a gas grill and an outdoor garden shower. Dining al fresco with friends and family a the patio dining area allows room for entertaining.
* PLEASE NOTE: Beaches are open to renters with permit. I would need to notarize a rental permit, so please let me know in advance if you would like to get one. It is $40 and the name on the agreement needs to match the registration. I have also included some beaches that do not require a permit.
Located in Greenport, this vacation home is in the city center and near the beach. Greenport Harbor Brewing Company and Kontokosta Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore The Hamptons Beaches and 67 Steps Beach. Greenport Carousel and East End Seaport Maritime Museum are also worth visiting. Kayaking and motor boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
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