Holiday Rentals in Cutchogue, NY

This eight-bedroom Water Mill house, situated near Bridgehampton, offers easy access to the Hamptons' beaches and villages.
The property boasts a private 5-acre plot, a new pool, a Har-Tru tennis court, a fully equipped gym with Peloton equipment, and accommodates up to 14 guests across the main house and a separate three-bedroom carriage house.

This charming five-bedroom house is situated on the picturesque North Fork, just a short drive from the historic village of Southold and its waterfront restaurants. It has received excellent ratings for its location, cleanliness, and overall user experience.
The property offers a flexible layout with a separate dining room, an open-plan living area, and a private suite with a workspace, perfect for families or groups of up to 10 guests. Enjoy the privacy of a secluded beach accessible via a staircase, stunning water views, a fully-equipped kitchen, multiple outdoor dining areas, and a private suite with its own bathroom and sitting area.

This Bridgehampton estate, a five-minute drive from both Bridgehampton and Sag Harbour villages, offers easy access to shops, restaurants, and beaches.
The 518 square metre property boasts six bedrooms, six and a half bathrooms, a heated saltwater pool, a spa, and ample space for large families or groups, including a gym and children's amenities.

This luxurious six-bedroom villa is located in Southampton, just 2.4 kilometres from Little Plains Beach and Flying Point Beach.
The property boasts a private swimming pool, sauna, and a fully equipped kitchen, ideal for large families or groups of friends looking for a relaxing stay.

This exclusive Water Mill estate, set within a private compound on 4.5 acres surrounded by reserves, offers a secluded retreat just a short drive from Mecox and Coopers Beach, with local amenities like King Kullen and Citarella within walking distance.
This luxurious six-bedroom, seven-bathroom villa, designed by an award-winning architect, accommodates up to 12 guests and boasts a chef's kitchen, a 15-metre heated swimming pool, private tennis court, cinema, sauna, and fitness centre for a resort-style experience.

This newly built luxury residence in East Marion offers proximity to award-winning wineries, farm-to-table dining in Greenport Village, and the Orient Point Ferry.
This modern coastal home accommodates up to 10 guests, featuring a chef's kitchen, a swimming pool, and seamless indoor-outdoor living, ideal for gatherings.

This Southold residence offers private beach access, a 5-minute walk or bike ride to August Acres Private Association Beach, and is a 5-kilometre drive from Greenport and Southold.
This four-bedroom, two-bathroom holiday home accommodates up to nine guests and features a heated outdoor swimming pool, four bicycles, a stand-up paddleboard, an enclosed outdoor shower, a fire pit, hammocks, and a basement playroom.

This Hampton Bays holiday home is situated 0.3km from West Landing Beach and a 3km drive from a shopping centre including King Kullen supermarket and Starbucks.
The 204 square metre property boasts six bedrooms, four bathrooms, sleeping up to 14 guests, a private heated pool, expansive deck, and a fully equipped kitchen.

This family-friendly holiday home is located in Water Mill, just 4.2 km from Channing Daughters Winery and 9.7 km from the Hamptons Beaches. It has received excellent user ratings, making it a popular choice for travellers.
The property offers 8 bedrooms and 8 bathrooms, providing spacious accommodation for up to 20 guests across its 743 square metres of floor area. Amenities include a private pool, fitness centre, tennis court, and a garden, ensuring a comfortable and enjoyable stay for the whole family.

This Southampton estate, located in a secluded, private area, offers proximity to renowned beaches like Cooper's Beach and Flying Point Beach, as well as Southampton Village's dining and shopping, just a few minutes away.
This expansive five-bedroom, three-bathroom residence accommodates up to 12 guests and features a fenced outdoor pool, bocce ball court, multiple fire pits, a wraparound deck, a converted barn with an exercise area, lounge, game room, and workstation, with world-class golf courses such as Shinnecock Hills and National Golf Links nearby.

Villa Hollow, a spacious 7-bedroom residence, is located in Hampton Bays, offering convenient access to local attractions yet situated away from the busiest areas.
This expansive villa, covering 465 square meters, accommodates up to 25 guests and features an infinity pool, a garden, a private terrace, an outdoor fireplace, and a fully equipped kitchen, with WiFi and private parking provided.

This Hampton Bays holiday home is situated 0.8km from Hampton Bays beaches, 4.8km from Regal UA Hampton Bays cinema, and 4.8km from Meschutt Beach, offering easy access to local attractions.
This five-bedroom, three-bathroom property boasts a spacious 1858 square metre floor area, sleeping up to ten guests, and includes a swimming pool, jacuzzi, and private patio, plus on-site water park access.

This Southampton Village house, situated in Tuckahoe, offers easy access to Coopers Beach and Southampton Village centre.
This five-bedroom, six-bathroom property boasts 372 square metres of living space, a private heated pool, and parking, accommodating up to six guests and one small dog (additional fee applies).

This private house is located in the woods of Noyack, a short drive from the charming village of Sag Harbor. It has excellent ratings for location, cleanliness, and user experience.
The house is spread over two acres of wooded land, accommodating up to 10 guests. It offers a range of amenities, including a private pool, hot tub, fitness centre, and a spacious deck with views of the surrounding woods.

This Sag Harbor holiday home, near Bay Street Theatre and the Sag Harbor Whaling and Historical Museum in North Haven, offers convenient access to other local attractions such as Eastville Heritage House and Havens House.
The five-bedroom, six-bathroom property sleeps ten guests, boasting a private guest area, upstairs sitting room, smart TVs in all bedrooms, a fenced gunite swimming pool, and parking; microwave and dishwasher are included in the kitchen.