
Sandy Beach, NY
10/20 – 10/23
$365/nighttotal: $1095 (3 )
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
06/27 – 07/01
$515/nighttotal: $2060 (4 )
House On First
1 2apartment , Greenport
This Greenport apartment rental is located two blocks from Greenport Village, offering easy walking access to shops, restaurants, beaches, Mitchell Park's antique carousel, and the Shelter Island ferry.
The two-bedroom unit features a full kitchen, dining room, private upstairs deck, and accommodates up to three guests with a living room daybed, plus private parking and in-unit amenities including air conditioning and a fitness center.
The two-bedroom unit features a full kitchen, dining room, private upstairs deck, and accommodates up to three guests with a living room daybed, plus private parking and in-unit amenities including air conditioning and a fitness center.

Sandy Beach, NY
10/20 – 10/28
$260/nighttotal: $2080 (8 )
Harbor Heights
2 2apartment , Greenport
This newly renovated Greenport Village two-family home offers two apartments, centrally located within walking distance of restaurants, shops, the Shelter Island Ferry, the Long Island Rail Road (LIRR), and the Hampton Jitney.
Each apartment features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher; air conditioning; a garden; parking; and accommodates up to six guests, with a combined capacity of twelve guests when both apartments are booked.
Each apartment features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher; air conditioning; a garden; parking; and accommodates up to six guests, with a combined capacity of twelve guests when both apartments are booked.

Sandy Beach, NY
10/20 – 10/28
$530/nighttotal: $4240 (8 )
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
2 2apartment , Greenport
Water's Edge luxury suite is located in the Captain's Roost Building of The Cliffside Resort Condominiums in Greenport, New York, on the North Fork of Long Island, with panoramic waterfront views from the master bedroom, living room, and private covered deck. Rated excellent by users for its location, cleanliness, and amenities, this two-bedroom, two-bathroom apartment accommodates up to 6 guests in 700 square feet.
The apartment features a fully equipped kitchenette with a dishwasher, air conditioning, a DVD player, a folding laptop table, a sturdy step ladder, a small vacuum, and cleaning supplies. Guests have access to a seasonal pool and coin-operated washer and dryer in the basement, as well as a private beach just yards away.
The apartment features a fully equipped kitchenette with a dishwasher, air conditioning, a DVD player, a folding laptop table, a sturdy step ladder, a small vacuum, and cleaning supplies. Guests have access to a seasonal pool and coin-operated washer and dryer in the basement, as well as a private beach just yards away.

Sandy Beach, NY
06/27 – 07/01
$552/nighttotal: $2208 (4 )
Two Bedroom Bungalow
1 2bungalow , Shelter Island Heights
This Shelter Island Heights bungalow is located one mile from Crescent Beach and the Shelter Island Heights village, offering easy access to swimming, dining, and shopping.
The recently renovated 2-bedroom, 1-bathroom cottage sleeps five, features a fully fenced yard with a deck, outdoor shower, and fire pit, plus a new washer/dryer and air conditioning.
The recently renovated 2-bedroom, 1-bathroom cottage sleeps five, features a fully fenced yard with a deck, outdoor shower, and fire pit, plus a new washer/dryer and air conditioning.

Sandy Beach, NY
10/20 – 10/23
$668/nighttotal: $2004 (3 )
Beach House In L.i. Wine Country
3 2apartment , Greenport
This newly renovated Greenport beach house is steps from Norman Klipp Marine Park's Gull Pond beach, a short walk from Greenport's historic village, and close to North Fork vineyards.
This three-bedroom, two-bathroom home sleeps six and features a new kitchen with modern appliances, central A/C, a washer/dryer, outdoor patio furniture, a BBQ grill, and ample parking.
This three-bedroom, two-bathroom home sleeps six and features a new kitchen with modern appliances, central A/C, a washer/dryer, outdoor patio furniture, a BBQ grill, and ample parking.

Sandy Beach, NY
06/27 – 07/01
$1488/nighttotal: $5952 (4 )
The Richmar Getaway
1 2apartment , East Marion
This waterfront apartment is located in Greenport, a short walk from the town's shops, galleries, and restaurants. It has received excellent ratings for user experience, location, and cleanliness.
This four-bedroom, three-bathroom home can accommodate up to 10 guests. Enjoy features like a hot tub, a fire pit, a garden, and a deck with stunning water views.
This four-bedroom, three-bathroom home can accommodate up to 10 guests. Enjoy features like a hot tub, a fire pit, a garden, and a deck with stunning water views.

Sandy Beach, NY
06/27 – 07/01
$602/nighttotal: $2408 (4 )
2-bedroom Park Model Cottage
1 2cabin , Greenport
This luxury park model, offering an outdoor escape, is located on over 23 acres at the eastern tip of Long Island's North Fork in Greenport.
Accommodating up to 6 guests, this cabin features 2 bedrooms, 1 bathroom, air conditioning, internet, a kitchen, parking, and access to resort amenities including a heated pool and pickleball courts.
Accommodating up to 6 guests, this cabin features 2 bedrooms, 1 bathroom, air conditioning, internet, a kitchen, parking, and access to resort amenities including a heated pool and pickleball courts.

Sandy Beach, NY
10/20 – 10/23
$400/nighttotal: $1200 (3 )
Vintage 1880 Victorian Gem.
1 2apartment , Greenport
This Greenport apartment rental is conveniently located a short walk from Greenport's shops and restaurants, and approximately 0.5 miles from the Shelter Island Ferry.
The one-bedroom, two-bathroom unit sleeps four guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, parking, and is ideal for group trips to explore Long Island's North Fork.
The one-bedroom, two-bathroom unit sleeps four guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning, a garden, parking, and is ideal for group trips to explore Long Island's North Fork.

Sandy Beach, NY
10/20 – 10/28
$321/nighttotal: $2568 (8 )
Blue Bay Dream W/ Seasonal Outdoor Jacuzzi, Cabana + Office
2 2apartment , Greenport
This Pipes Cove vacation home is a short walk from the Railroad Museum of Long Island and East End Seaport Maritime Museum, and within 10 minutes of the Greenport Carousel and Camera Obscura, with Greenport Station a 3-minute walk away.
This 800-square-foot house features three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, Jacuzzi, and a terrace with barbecue grills; free Wi-Fi is provided.
This 800-square-foot house features three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, Jacuzzi, and a terrace with barbecue grills; free Wi-Fi is provided.

Sandy Beach, NY
10/20 – 10/23
$493/nighttotal: $1479 (3 )
Greenport Getaway
3 2apartment , Greenport
This newly built ranch home is located in Greenport, just minutes from a private beach and conveniently close to local shops and restaurants.
This 3-bedroom, 2-bathroom residence accommodates up to 6 guests and features a private heated outdoor pool, a gourmet kitchen with stainless steel appliances, a wood-burning fireplace, and a pool table for indoor entertainment.
This 3-bedroom, 2-bathroom residence accommodates up to 6 guests and features a private heated outdoor pool, a gourmet kitchen with stainless steel appliances, a wood-burning fireplace, and a pool table for indoor entertainment.

Sandy Beach, NY
06/27 – 07/01
$1414/nighttotal: $5656 (4 )
Cozy Greenport Village Cottage
4 2apartment , Greenport
This family-friendly apartment is situated in the rural Pipes Cove district of Greenport, a 7-minute walk from the Long Island Railroad Museum and an 11-minute walk from the Antique Carousel, with Greenport train station just 9 minutes away.
This 1800 square foot vacation home accommodates up to 8 guests and features 4 bedrooms, 4 bathrooms, air conditioning, free Wi-Fi, a full kitchen with an ice dispenser, and outdoor amenities like a fire pit and barbecue.
This 1800 square foot vacation home accommodates up to 8 guests and features 4 bedrooms, 4 bathrooms, air conditioning, free Wi-Fi, a full kitchen with an ice dispenser, and outdoor amenities like a fire pit and barbecue.













