
Duck Walk Vineyards, Southold
10/12 – 10/20
$356/nighttotal: $2848 (8 )
Charming Hampton Bays Home 5 Mi To Cooper’s Beach
1 2house , Hampton Bays
This three-bedroom vacation home in Hampton Bays is conveniently located within walking distance to Hampton Bays Station and close to popular beaches. It has received excellent ratings for its location, cleanliness, and user experience.
The 1,300 square-foot house features a fully equipped kitchen, a DVD player, a spa tub, and a garden with barbecue grills. It can accommodate up to six guests and is pet-friendly.
The 1,300 square-foot house features a fully equipped kitchen, a DVD player, a spa tub, and a garden with barbecue grills. It can accommodate up to six guests and is pet-friendly.

Duck Walk Vineyards, Southold
09/01 – 09/07
$597/nighttotal: $3582 (6 )
New Suffolk Beach Cottage 1 | North Fork
2 4apartment , New Suffolk
This charming cottage is just a minute from the private sandy beaches of Peconic Bay in the desirable hamlet of New Suffolk, known for its beautiful beaches and charming atmosphere. It has received excellent ratings for location, cleanliness, and overall user experience.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy the private porch, BBQ, outdoor shower, and bikes, perfect for relaxing and exploring the beautiful North Fork.
The cottage has two bedrooms and one bathroom, comfortably accommodating up to four guests. Enjoy the private porch, BBQ, outdoor shower, and bikes, perfect for relaxing and exploring the beautiful North Fork.

Duck Walk Vineyards, Southold
09/01 – 09/07
$792/nighttotal: $4752 (6 )
Greenport Condo With Stunning Views & Beach Access
2 4apartment , Greenport
This 2-bedroom condo offers a cliffside location on the Long Island Sound in Greenport, providing direct access to local wineries and farms on the North Fork.
This accommodation features air conditioning, a kitchen with a microwave and dishwasher, and parking, with a guest capacity of six, ideal for exploring the natural beauty and attractions of the North Fork.
This accommodation features air conditioning, a kitchen with a microwave and dishwasher, and parking, with a guest capacity of six, ideal for exploring the natural beauty and attractions of the North Fork.

Duck Walk Vineyards, Southold
06/29 – 07/06
$1333/nighttotal: $9331 (7 )
Tranquil Farm Setting In The Heart Of North Fork
1 4apartment , Southold
This Southold apartment is just a short drive from Southold town, Horton Point lighthouse, Mcbain beach, and Greenport Village, nestled in a peaceful farm setting. It boasts excellent user, location, and cleanliness ratings.
The 5-bedroom, 2-bathroom dwelling comfortably accommodates up to 10 guests. Enjoy modern amenities like smart TVs, a surround sound system, high-speed Wi-Fi, a fully stocked kitchen, a Weber BBQ, and an in-ground saltwater pool.
The 5-bedroom, 2-bathroom dwelling comfortably accommodates up to 10 guests. Enjoy modern amenities like smart TVs, a surround sound system, high-speed Wi-Fi, a fully stocked kitchen, a Weber BBQ, and an in-ground saltwater pool.

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
$557/nighttotal: $3342 (6 )
Peaceful Guesthouse
1 4apartment , Laurel
This Laurel, Maryland B&B is a half-mile walk from the beach, one mile from restaurants, and within five miles of local wineries, breweries, and golf courses.
This two-bedroom guesthouse sleeps four adults (plus an infant in a pack 'n play), features a full kitchen, dining room, living area with fireplace, an outdoor patio with a fireplace, and one and a half bathrooms.
This two-bedroom guesthouse sleeps four adults (plus an infant in a pack 'n play), features a full kitchen, dining room, living area with fireplace, an outdoor patio with a fireplace, and one and a half bathrooms.

Duck Walk Vineyards, Southold
06/29 – 07/06
$1259/nighttotal: $8813 (7 )
West Neck Landing - Waterfront On Shelter Island
1 4apartment , Shelter Island Heights
This Shelter Island Heights apartment is located just 20 feet from the water's edge on West Neck Bay, offering stunning views and direct access to the water. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom, two-bathroom vacation rental comfortably sleeps four guests. It features a private dock, a porch, and a patio, perfect for enjoying meals, cocktails, and the beautiful views. You can also enjoy activities like kayaking, clamming, and swimming, and are within easy walking distance of the beach.
This two-bedroom, two-bathroom vacation rental comfortably sleeps four guests. It features a private dock, a porch, and a patio, perfect for enjoying meals, cocktails, and the beautiful views. You can also enjoy activities like kayaking, clamming, and swimming, and are within easy walking distance of the beach.

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
10/12 – 10/20
$294/nighttotal: $2352 (8 )
Greenport Village Relaxation
1 2apartment , Greenport
This Greenport Village rental is a two-bedroom, one-bathroom cottage located in the Historic District, a 10-minute walk from the village center and 12 minutes from the train and Jitney stops.
The 2-bedroom home offers a backyard grill, sleeps four, includes a fridge, microwave, and dishwasher, and is near Alice's Fish Market, Barba Bianca, and Kontokosta Winery.
The 2-bedroom home offers a backyard grill, sleeps four, includes a fridge, microwave, and dishwasher, and is near Alice's Fish Market, Barba Bianca, and Kontokosta Winery.

Duck Walk Vineyards, Southold
10/10 – 10/16
$370/nighttotal: $2220 (6 )
Newly Built Ranch, Beautifully Landscaped With Pool, Large Yard, Patio,...
3 1apartment , Greenport
This Greenport vacation home is conveniently located less than a mile from Kontokosta Winery and 67 Steps Beach, and within two miles of Stony Brook Eastern Long Island Hospital.
This 1650-square-foot house features three bedrooms, two bathrooms, a private pool, and a fully equipped kitchen, comfortably accommodating up to six guests and offering access to a fitness center, gas grills, and a private yard.
This 1650-square-foot house features three bedrooms, two bathrooms, a private pool, and a fully equipped kitchen, comfortably accommodating up to six guests and offering access to a fitness center, gas grills, and a private yard.

Duck Walk Vineyards, Southold
06/29 – 07/06
$1115/nighttotal: $7805 (7 )
Cozy Beach House - Steps From Beach W/ Water Views
3 4apartment , Greenport
This Greenport cottage offers unbeatable proximity to 5th Street Beach, just steps away, and is within easy walking distance to Greenport Village shops, restaurants, and the LIRR station.
This 3-bedroom, 2-bathroom rental sleeps up to 6 guests and features water views from the bedrooms, two living areas, a spacious backyard with a garden, high-speed WiFi, a Smart TV, and central cooling and heating.
This 3-bedroom, 2-bathroom rental sleeps up to 6 guests and features water views from the bedrooms, two living areas, a spacious backyard with a garden, high-speed WiFi, a Smart TV, and central cooling and heating.

Duck Walk Vineyards, Southold
06/29 – 07/06
$783/nighttotal: $5481 (7 )
2-bedroom Park Model Cottage
1 4cabin , 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.













