
Croteaux Vineyards, Southold
10/16 – 10/19
$870/nighttotal: $2610 (3 )
Private Beachfront Getaway
1 2bungalow , Southold
This beachfront Southold cottage offers direct private beach access and is conveniently located near Southold Village, allowing easy exploration of local shops and restaurants.
The 2-bedroom, 1-bathroom home sleeps four, features a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, and a wrap-around deck with BBQ grill; no pets are allowed.
The 2-bedroom, 1-bathroom home sleeps four, features a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, and a wrap-around deck with BBQ grill; no pets are allowed.

Croteaux Vineyards, Southold
06/23 – 07/01
$1437/nighttotal: $11496 (8 )
Haven On Glynn By Rove Travel | 3br Coastal Luxury
3 2apartment , Shelter Island Heights
This Shelter Island Heights rental is located within 1 mile of Sylvester Manor, Havens House, and Shelter Island Country Club.
This apartment offers air conditioning, a balcony, a garden, and a kitchen equipped with a fridge, microwave, and dishwasher, with parking available.
This apartment offers air conditioning, a balcony, a garden, and a kitchen equipped with a fridge, microwave, and dishwasher, with parking available.

Croteaux Vineyards, Southold
10/16 – 10/19
$710/nighttotal: $2130 (3 )
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.

Croteaux Vineyards, Southold
06/25 – 07/05
$1502/nighttotal: $15020 (10 )
Idyllic Shelter Island Beach House
1 2apartment , Shelter Island Heights
This retro 60's modern A-frame beach house is located in Shelter Island Heights, a 3-minute walk from Crab Creek Beach and steps from the creek, offering direct creek access for kayaking and paddleboarding.
This 6-guest capacity dwelling features 2 bathrooms, a secluded garden with a 70-foot-long swimming pool, a high-ceiling living room with a wood-burning stove, a unique loft workspace with a queen bed, and a patio for outdoor dining.
This 6-guest capacity dwelling features 2 bathrooms, a secluded garden with a 70-foot-long swimming pool, a high-ceiling living room with a wood-burning stove, a unique loft workspace with a queen bed, and a patio for outdoor dining.

Croteaux Vineyards, Southold
06/23 – 07/01
$1111/nighttotal: $8888 (8 )
Enjoy Driftwood Landing - A Quiet Southold Escape
3 2apartment , Southold
This Southold vacation rental offers a secluded escape, located within 1 mile of the Railroad Museum of Long Island and the East End Seaport Maritime Museum, and a short drive to Croteaux Vineyards and Corey Creek Winery.
This 3-bedroom, 2-bathroom home accommodates up to 6 guests and features air conditioning and internet, providing a comfortable base for exploring family-friendly attractions like 8 Hands Farm and the Greenport Carousel.
This 3-bedroom, 2-bathroom home accommodates up to 6 guests and features air conditioning and internet, providing a comfortable base for exploring family-friendly attractions like 8 Hands Farm and the Greenport Carousel.

Croteaux Vineyards, Southold
06/25 – 07/05
$1035/nighttotal: $10350 (10 )
North Fork Waterfront Beach House
1 2apartment , Southold
This waterfront home with a private beach is located on the North Fork of Southold, 7 minutes from Greenport and near local vineyards and farm stands.
This apartment features direct waterfront access, a private beach, an open floor plan with Sound views, a fully equipped kitchen with a wine refrigerator, and a spacious deck with a BBQ, accommodating up to 6 guests with a queen bed, twin beds, and a queen-size sleeper sofa.
This apartment features direct waterfront access, a private beach, an open floor plan with Sound views, a fully equipped kitchen with a wine refrigerator, and a spacious deck with a BBQ, accommodating up to 6 guests with a queen bed, twin beds, and a queen-size sleeper sofa.

Croteaux Vineyards, Southold
09/01 – 09/03
$576/nighttotal: $1152 (2 )
2-bedroom Park Model Cottage
1 5cabin , 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.

Croteaux Vineyards, Southold
10/16 – 10/19
$1678/nighttotal: $5034 (3 )
Mansion Near The Bay. 7 Bedrooms! Chefs Kitchen.
7 2apartment , North Sea
This manor house is located in Southampton, a short drive from both Sag Harbor and Southampton villages. The house is rated excellent by previous guests.
This 6,600 square foot estate comfortably sleeps up to 16 guests. The house offers a private beach, a heated pool, a playground, a BBQ grill, a ping pong table, kayaks, paddleboards, fishing poles, a dive dock, a kids' room, and bicycles.
This 6,600 square foot estate comfortably sleeps up to 16 guests. The house offers a private beach, a heated pool, a playground, a BBQ grill, a ping pong table, kayaks, paddleboards, fishing poles, a dive dock, a kids' room, and bicycles.

Croteaux Vineyards, Southold
10/16 – 10/19
$611/nighttotal: $1833 (3 )
Secluded Hamptons Cottage
2 2apartment , Noyack
Located near Noyac Golf Club, this ski-in/ski-out vacation home is situated in Sag Harbor, close to The Hamptons Beaches and Elizabeth A. Morton National Wildlife Refuge. It has excellent user, location, and cleanliness ratings.
The house has 2 bedrooms and 1 bathroom, accommodating up to 4 guests. It features a kitchen with a refrigerator and oven, free Wi-Fi, and a private fenced yard with a barbecue grill. Guests can also enjoy amenities like air conditioning, a spa, and parking.
The house has 2 bedrooms and 1 bathroom, accommodating up to 4 guests. It features a kitchen with a refrigerator and oven, free Wi-Fi, and a private fenced yard with a barbecue grill. Guests can also enjoy amenities like air conditioning, a spa, and parking.

Croteaux Vineyards, Southold
06/25 – 07/05
$1311/nighttotal: $13110 (10 )
West Neck Landing - Waterfront On Shelter Island
1 2apartment , 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.

Croteaux Vineyards, Southold
09/01 – 09/03
$1002/nighttotal: $2004 (2 )
3br/2ba Greenport Cottage: Walk, Water And Wine!
1 5apartment , Greenport
This Greenport apartment is located within a block or two of the beach, marinas, Kontokosta Winery, and Lin Beach House, and is a 10-minute walk to downtown Greenport with LIRR, Shelter Island, and Sag Harbor ferries.
This 3-bedroom rental accommodates up to 9 guests with WiFi, smart TVs, central air conditioning, a gas grill, fire pit, and a screened-in porch overlooking the winery.
This 3-bedroom rental accommodates up to 9 guests with WiFi, smart TVs, central air conditioning, a gas grill, fire pit, and a screened-in porch overlooking the winery.

Croteaux Vineyards, Southold
09/01 – 09/03
$1622/nighttotal: $3244 (2 )
Beachfront Greenport Villa
1 5apartment , Southold
Villa Sonore, a beachfront Greenport property in Southold, offers easy walking access to Soundview's restaurants and bars and is a short bike ride from North Fork wineries and breweries.
This three-bedroom, two-bathroom house sleeps eight guests and includes amenities such as paddleboards, bicycles, and beach chairs, plus a driveway for three cars and a private enclosed porch and back deck with stunning Long Island Sound views.
This three-bedroom, two-bathroom house sleeps eight guests and includes amenities such as paddleboards, bicycles, and beach chairs, plus a driveway for three cars and a private enclosed porch and back deck with stunning Long Island Sound views.












