
Duck Walk Vineyards, Southold
06/29 – 07/06
$630/nighttotal: $4410 (7 )
The Bay Breeze
2 4cottage , Cutchogue
The Bay Breeze cottage is located in Cutchogue, overlooking East/Eugenes Creek, and is a short bike ride from local wineries, farms, and restaurants. The cottage has excellent user, location, and cleanliness ratings.
The cottage has a spacious open floor plan and can accommodate up to four guests. Amenities include a private dock, a boat slip, a large deck, a fire pit, a gas griddle, a luxurious outdoor shower, and a fully equipped kitchen.
The cottage has a spacious open floor plan and can accommodate up to four guests. Amenities include a private dock, a boat slip, a large deck, a fire pit, a gas griddle, a luxurious outdoor shower, and a fully equipped kitchen.

Duck Walk Vineyards, Southold
09/01 – 09/07
$768/nighttotal: $4608 (6 )
Charming 2 Bedroom Apt In Dwntwn Greenport
1 4apartment , Greenport
This Greenport apartment rental is centrally located, within walking distance of the Long Island Rail Road, the Hampton Jitney bus service, and downtown Greenport's shops and beaches.
The newly renovated two-bedroom unit sleeps four, features a microwave, air conditioning, parking, and is situated above a wine boutique, offering guests privacy and proximity to fine dining.
The newly renovated two-bedroom unit sleeps four, features a microwave, air conditioning, parking, and is situated above a wine boutique, offering guests privacy and proximity to fine dining.

Duck Walk Vineyards, Southold
06/29 – 07/06
$2461/nighttotal: $17227 (7 )
Stunning Home & Private Beach On The North Fork
1 4apartment , Southold
This beautiful home is located on the scenic North Fork, just a short distance from the charming village of Southold. The house offers stunning views of the Long Island Sound and has received excellent ratings for cleanliness, location, and overall experience.
This spacious house has five bedrooms and can accommodate up to ten guests. The home features a chef's kitchen, multiple outdoor spaces, a private beach, and a comfortable layout, perfect for families and groups looking for a relaxing and enjoyable vacation.
This spacious house has five bedrooms and can accommodate up to ten guests. The home features a chef's kitchen, multiple outdoor spaces, a private beach, and a comfortable layout, perfect for families and groups looking for a relaxing and enjoyable vacation.

Duck Walk Vineyards, Southold
10/23 – 10/25
$794/nighttotal: $1588 (2 )
Southold Sea'renity
3 4apartment , Southold
This three-bedroom Southold house is steps from a fishing lake and six houses from Kenny's Beach, offering unparalleled access to Southold's waterfront attractions.
The completely remodeled home features three queen beds and two twin beds, accommodating six guests comfortably, and includes a full kitchen, air conditioning, a jacuzzi, parking, and kayaks for exploring the nearby waters; enjoy a hot tub, fire pit, and BBQ on the brand-new deck.
The completely remodeled home features three queen beds and two twin beds, accommodating six guests comfortably, and includes a full kitchen, air conditioning, a jacuzzi, parking, and kayaks for exploring the nearby waters; enjoy a hot tub, fire pit, and BBQ on the brand-new deck.

Duck Walk Vineyards, Southold
06/29 – 07/06
$555/nighttotal: $3885 (7 )
Fishermans Cottage Close To Sunset Beach
2 4apartment , Shelter Island Heights
This two-bedroom, one-bathroom rental unit offers 1,000 square feet of living space for up to four guests, featuring a full kitchen, air conditioning, and internet access in a secluded woodland setting. Located just a 5-minute walk from Crescent Beach, Perlman Music, and The Pridwin Hotel, this accommodation provides a tranquil escape with abundant wildlife sightings.

Duck Walk Vineyards, Southold
10/12 – 10/20
$738/nighttotal: $5904 (8 )
Shelter Bay Cove Waterfront + Beach + Spectacular
3 2apartment , Southold
This Southold apartment is located in Shelter Bay on the North Fork, offering 90 feet of private waterfront on the Hashamomuck Inlet and a short distance to Long Island Sound beach. It boasts excellent user ratings for location, cleanliness, and overall experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to seven guests. Enjoy modern amenities like central air conditioning, cable TV, Wi-Fi, a washer/dryer, a fully equipped kitchen, and a private sandy beach perfect for swimming, kayaking, and clamming.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to seven guests. Enjoy modern amenities like central air conditioning, cable TV, Wi-Fi, a washer/dryer, a fully equipped kitchen, and a private sandy beach perfect for swimming, kayaking, and clamming.

Duck Walk Vineyards, Southold
10/12 – 10/20
$401/nighttotal: $3208 (8 )
The Olde Church In Greenport
1 2apartment , Greenport
This unique Greenport lodging, a converted 1867 church, is centrally located within walking distance of Greenport's restaurants, shops, the beach, the Long Island Rail Road (LIRR), and the Jitney.
The renovated church features a modern kitchen with microwave and dishwasher, a king-size bed in the upstairs bedroom, a living room with fireplace and 65" TV, accommodates two guests, and includes a two-hour electric bike rental for exploring Greenport, Orient Point, or Shelter Island.
The renovated church features a modern kitchen with microwave and dishwasher, a king-size bed in the upstairs bedroom, a living room with fireplace and 65" TV, accommodates two guests, and includes a two-hour electric bike rental for exploring Greenport, Orient Point, or Shelter Island.

Duck Walk Vineyards, Southold
10/23 – 10/25
$434/nighttotal: $868 (2 )
Charming Home In Village Center!
1 4apartment , Greenport
This Greenport apartment rental is centrally located less than two blocks from the Greenport Carousel and within walking distance of shops, restaurants, the Long Island Rail Road (LIRR) station, and the Shelter Island Ferry.
The two-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen with dishwasher, air conditioning, a fenced yard, and a screened-in porch; pet-friendly with pre-approval.
The two-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen with dishwasher, air conditioning, a fenced yard, and a screened-in porch; pet-friendly with pre-approval.

Duck Walk Vineyards, Southold
10/12 – 10/20
$537/nighttotal: $4296 (8 )
Lovely 2-bedroom Apartment In A Historic Home
1 2apartment , Greenport
This Greenport Village rental is a two-bedroom, one-bathroom apartment a short walk from Greenport's shops, restaurants, the Long Island Rail Road, the Hampton Jitney, and Shelter Island Ferry, and a 10-minute walk to local beaches.
The unit features a fully equipped kitchen with Bosch appliances, a newly refinished clawfoot tub and a separate shower, a private entrance with electronic keypad, and accommodates up to three guests; enjoy nearby sunrise/sunset views from the dock, a two-minute walk away.
The unit features a fully equipped kitchen with Bosch appliances, a newly refinished clawfoot tub and a separate shower, a private entrance with electronic keypad, and accommodates up to three guests; enjoy nearby sunrise/sunset views from the dock, a two-minute walk away.

Duck Walk Vineyards, Southold
06/29 – 07/06
$1717/nighttotal: $12019 (7 )
Bright Beach House With Private Beach Access
1 4apartment , Shelter Island Heights
This Shelter Island Heights vacation home is near Crescent Beach, a short drive from the Pridwin Hotel and Leon's restaurant.
This four-bedroom, two-bathroom house sleeps ten, features a fully equipped kitchen with high-end appliances, multiple outdoor spaces including decks and a screened porch, and provides private beach access for swimming, kayaking, and paddle boarding.
This four-bedroom, two-bathroom house sleeps ten, features a fully equipped kitchen with high-end appliances, multiple outdoor spaces including decks and a screened porch, and provides private beach access for swimming, kayaking, and paddle boarding.

Duck Walk Vineyards, Southold
09/01 – 09/07
$644/nighttotal: $3864 (6 )
House Of Classic Arts And Crafts North Fork
3 4apartment , Southold
This charming Southold village house is located in the center of town, within walking distance of shops and a short drive from wineries, bay and sound beaches. Travelers have rated this property excellent, making it a popular choice for those seeking a comfortable and convenient stay. This three-bedroom, two-bathroom home spans 2200 square feet, offering ample space for families or groups of friends. Guests can enjoy the spacious backyard, relax on the deck, or take advantage of the many amenities, including a fully equipped kitchen, air conditioning, and access to the internet.

Duck Walk Vineyards, Southold
10/12 – 10/20
$387/nighttotal: $3096 (8 )
Private 1st Flr Apt W/ Patio 3 Blocks From Beach
1 2apartment , Greenport
This Greenport apartment is located in a quiet neighborhood, just blocks from the beach, train station, restaurants, and a park. It has excellent user, location, and cleanliness ratings.
This comfortable rental has one bedroom and one bathroom, accommodating up to four guests. You'll enjoy a private entrance, patio, a fully equipped kitchen, air conditioning, a garden, and parking.
This comfortable rental has one bedroom and one bathroom, accommodating up to four guests. You'll enjoy a private entrance, patio, a fully equipped kitchen, air conditioning, a garden, and parking.













