House in Greenport, NY
5 guests · 3 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
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.
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.
Amenities at 1820 Whaling Captain's Home - A walk to a coffee or cocktail!
Non-smoking
Pets allowed
Family friendly
Map of Greenport, NY
Ratings and reviews
Summary of reviewsThe property is beautifully maintained with an amazing garden, charming decor, fully equipped kitchen, and cozy rooms. The location is ideal for exploring the town and nearby attractions.
10 / 10Outstanding·Aug 2025
This lovely historic home served as the perfect backdrop for a few weeks of summer fun in Greenport! The mature garden is a fantastic place to relax and entertain, and the house is comfortable, well-equipped and beautifully appointed!
10 / 10Outstanding·Jul 2025
Property is super clean , cozy , amazing backyard with spectacular landscaping … little pond with koi fish adds such a unique touch to it …If ever back to Greenport will definitely stay there again !
10 / 10Outstanding·Jul 2025
We stayed for a week and enjoyed every single thing about this home! The house feels loved and lived in and makes you feel like you’re staying with friend or family, not a sterile rental! The bedrooms are all a good size and beds were all very comfortable! The gorgeous renovated kitchen was a joy to cook meals in and the backyard was perfect! We enjoyed days and nights on the deck and in the secret garden! The location was perfect for walking to Front St restaurants and shops, ferry to Shelter Island and LIRR station. Hosts were so quick to respond and answer any questions that came up! Would definitely stay again!
5 / 10·Sep 2021
Girls getaway with my friend and my dog. Marcia was wonderful, gave Really thoughtful recommendations and even left us a bottle of vino upon our arrival! House is really lovely and the location perfect: walkable to town and just a short jaunt to the beaches was ideal!!!
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Top rated by guests
10Outstanding
(59 Ratings)
The property is beautifully maintained with an amazing garden, charming decor, fully equipped kitchen, and cozy rooms. The location is ideal for exploring the town and nearby attractions.
From real guest reviews summarized by AIDon't miss out! Price and availability may change
