
Sandy Beach, NY
10/07 – 10/16
$507/nighttotal: $4563 (9 )
Waterfront Escape | Private Beach, Pool & Views
1 2apartment , Greenport
This Greenport waterfront condo offers an excellent stay for up to 6 guests. It is located on a bluff overlooking Long Island Sound, minutes from downtown Greenport. Reviewers rate the location, cleanliness, and the overall property as excellent.
The condo has two bedrooms and two bathrooms. It features a private waterfront deck with grills and a private beach, a kitchenette, a smart TV, and a record player. Guests also have access to a shared pool, a great lawn, and a laundry room. The condo is close to Greenport's historic seaport, farms, wineries, and restaurants.
The condo has two bedrooms and two bathrooms. It features a private waterfront deck with grills and a private beach, a kitchenette, a smart TV, and a record player. Guests also have access to a shared pool, a great lawn, and a laundry room. The condo is close to Greenport's historic seaport, farms, wineries, and restaurants.

Sandy Beach, NY
10/09 – 10/17
$1071/nighttotal: $8568 (8 )
Elegant Greenport Victorian-winter Harbor House-
1 6apartment , Greenport
Winter Harbor House is a stylish Victorian home located in Greenport Village, just a short walk from Mitchell Park and the North Ferry to Shelter Island. The home has received excellent ratings for its location, cleanliness, and overall experience.
Winter Harbor House can accommodate up to 13 guests in its four bedrooms and four bathrooms. The house features a well-equipped kitchen, a spacious living area, a relaxing garden, a fitness center, and parking for multiple vehicles.
Winter Harbor House can accommodate up to 13 guests in its four bedrooms and four bathrooms. The house features a well-equipped kitchen, a spacious living area, a relaxing garden, a fitness center, and parking for multiple vehicles.

Sandy Beach, NY
10/07 – 10/16
$285/nighttotal: $2565 (9 )
Quiet Neighborhood And Only Steps To Town
1 2apartment , Greenport
This charming Greenport apartment is located on a lovely street, just a short 5-minute walk from the town center and the harbor. The apartment has excellent user, location, and cleanliness ratings. This cozy apartment has one bedroom and one bathroom, comfortably accommodating two guests. Enjoy harbor views from the bedroom and kitchen, along with a newly renovated space, air conditioning, parking, and internet access.

Sandy Beach, NY
10/09 – 10/17
$871/nighttotal: $6968 (8 )
Charming 3-bedroom Cottage In Fabulous Greenport
3 6cottage , Greenport
This Greenport, New York cottage, a converted 1870s schoolhouse, is conveniently located near Greenport village, Kontokosta Winery, and Safe Harbor Stirling.
This three-bedroom, two-bathroom house sleeps seven and boasts a fully equipped kitchen, a large fenced backyard with a deck, patio, fire pit, and hammock, plus entertainment options including a Roku TV, Xbox 360, and PlayStation 3.
This three-bedroom, two-bathroom house sleeps seven and boasts a fully equipped kitchen, a large fenced backyard with a deck, patio, fire pit, and hammock, plus entertainment options including a Roku TV, Xbox 360, and PlayStation 3.

Sandy Beach, NY
10/07 – 10/16
$338/nighttotal: $3042 (9 )
Charming Greenport Gem 1, 1 Mile To Ferry!
1 2apartment , Greenport
This smoke-free apartment is conveniently located in Greenport, just a short walk from the Greenport Farmers' Market, Camera Obscura, and Greenport Carousel. The apartment offers easy access to the town's main attractions, including the bustling waterfront, the marina, and the Greenport Station.
This rental features a fully equipped kitchen with a microwave, dishwasher, and oven, a comfortable living area with a TV and ceiling fan, and a bathroom with a shower. The apartment building offers free parking and Wi-Fi in public areas, ensuring a convenient and comfortable stay.
This rental features a fully equipped kitchen with a microwave, dishwasher, and oven, a comfortable living area with a TV and ceiling fan, and a bathroom with a shower. The apartment building offers free parking and Wi-Fi in public areas, ensuring a convenient and comfortable stay.

Sandy Beach, NY
10/09 – 10/17
$1269/nighttotal: $10152 (8 )
Greenport Village Walking Distance To All
3 6apartment , Greenport
This Greenport vacation home is an excellent choice for a memorable stay, located in the heart of the village, a short walk from the shops and restaurants. With a user rating of excellent, this 3-bedroom, 2-bathroom island vacation home can accommodate up to 9 guests, offering a spacious layout and a private patio.
Guests can enjoy a relaxing soak in the hot tub, cook meals in the fully equipped kitchen, or simply unwind in the comfortable living area. The enclosed patio provides a secluded outdoor space for dining, while the proximity to the beach offers easy access to swimming, sunbathing, or water sports.
Guests can enjoy a relaxing soak in the hot tub, cook meals in the fully equipped kitchen, or simply unwind in the comfortable living area. The enclosed patio provides a secluded outdoor space for dining, while the proximity to the beach offers easy access to swimming, sunbathing, or water sports.

Sandy Beach, NY
10/09 – 10/17
$1261/nighttotal: $10088 (8 )
Gorgeous 5 Bdrm Home With Beautiful Bay Views In The Heart Of Greenport Village
5 6apartment , Greenport
This Greenport vacation home is conveniently located within walking distance of the Greenport Farmers' Market, Camera Obscura, and East End Seaport Maritime Museum, making it ideal for exploring the town's attractions. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The house offers 4 bedrooms, accommodating up to 10 guests, making it perfect for families or groups. Enjoy modern amenities like free Wi-Fi, a fully equipped kitchen, a private garden, and a spa, perfect for relaxing after a day of exploring.
The house offers 4 bedrooms, accommodating up to 10 guests, making it perfect for families or groups. Enjoy modern amenities like free Wi-Fi, a fully equipped kitchen, a private garden, and a spa, perfect for relaxing after a day of exploring.

Sandy Beach, NY
10/07 – 10/16
$298/nighttotal: $2682 (9 )
Charming Greenport Gem 1, 1 Mile To Ferry!
2 2apartment , Greenport
This Greenport apartment is conveniently located just a mile from the ferry, making it easy to explore the North Fork and beyond, and it's also a short drive from the popular Splish Splash water park. This rental has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers 900 square feet of space, with two bedrooms and one bathroom, comfortably accommodating up to six guests. You'll enjoy a fully equipped kitchen, air conditioning, free Wi-Fi, a terrace or balcony, and a garden, perfect for relaxing and enjoying the Greenport atmosphere.
The apartment offers 900 square feet of space, with two bedrooms and one bathroom, comfortably accommodating up to six guests. You'll enjoy a fully equipped kitchen, air conditioning, free Wi-Fi, a terrace or balcony, and a garden, perfect for relaxing and enjoying the Greenport atmosphere.

Sandy Beach, NY
10/09 – 10/17
$512/nighttotal: $4096 (8 )
Designer Renovated Farmhouse With Pool
1 6apartment , Shelter Island
This renovated 1860s farmhouse on Shelter Island offers easy ferry access from both the Hamptons and the North Fork, placing you near Shelter Island's pristine beaches and restaurants.
The three-bedroom, two-bathroom property sleeps six guests and boasts a heated pool, jacuzzi, outdoor shower, two outdoor dining areas, three fireplaces, and modern amenities including a fully equipped kitchen, dishwasher, and Wi-Fi.
The three-bedroom, two-bathroom property sleeps six guests and boasts a heated pool, jacuzzi, outdoor shower, two outdoor dining areas, three fireplaces, and modern amenities including a fully equipped kitchen, dishwasher, and Wi-Fi.

Sandy Beach, NY
10/09 – 10/17
$809/nighttotal: $6472 (8 )
Relaxation In Greenport
1 6apartment , Greenport
This newly renovated Greenport house, ideally situated two blocks from the Hampton Jitney, Long Island Rail Road, and Shelter Island Ferry, provides easy access to Main Street's restaurants and bars and is a three-minute drive from Greenport's beaches.
The three-bedroom, two-bathroom home sleeps eight guests and boasts high-end appliances (Sub-Zero refrigerator, Wolf range, Bosch dishwasher), two Smart TVs (55" and 65"), central air conditioning, a fenced yard, and ample parking.
The three-bedroom, two-bathroom home sleeps eight guests and boasts high-end appliances (Sub-Zero refrigerator, Wolf range, Bosch dishwasher), two Smart TVs (55" and 65"), central air conditioning, a fenced yard, and ample parking.

Sandy Beach, NY
10/07 – 10/16
$484/nighttotal: $4356 (9 )
Waterfront Greenport Condo
1 2apartment , Greenport
This Cliffside Resort condo in Greenport, Long Island offers stunning Long Island Sound views and private beach access.
The two-bedroom, two-bathroom unit sleeps six and includes a kitchen with a fridge and dishwasher, air conditioning, parking, and access to a heated resort pool; resort amenities include a lawn perfect for picnics and barbecues.
The two-bedroom, two-bathroom unit sleeps six and includes a kitchen with a fridge and dishwasher, air conditioning, parking, and access to a heated resort pool; resort amenities include a lawn perfect for picnics and barbecues.

Sandy Beach, NY
10/09 – 10/17
$1155/nighttotal: $9240 (8 )
Greenport Family Retreat/walk To Town/pool/beaches
1 6apartment , Greenport
This 4-bedroom, 2-bathroom rental home in Greenport is located on a quiet, tree-lined street, just a 10-minute walk from the LIRR, Hampton Jitney, and North Ferry terminals.
This pet-friendly residence accommodates up to 8 guests and features a fully equipped kitchen, air conditioning, a swimming pool, and a backyard with a fire pit for all-season enjoyment.
This pet-friendly residence accommodates up to 8 guests and features a fully equipped kitchen, air conditioning, a swimming pool, and a backyard with a fire pit for all-season enjoyment.













