luxury houses for rent Greenport, United States

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards.

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village.This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away.The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches.

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Offered Apr $10,000; May $12,000; June $15,000; July $35,000; Aug $35,000; Sept $20,000; Oct $15,000; Nov $10,000. Permit# 1020.

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered May $7,000; Aug 12-26 $10,000; Sept $10,000; Oct $7,000; Nov $6,000. Permit #0483.

2025 Rates: June $30,000, July $60,000, July-August $125,000 and August-Labor Day $65,000. This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio. Inside, the foyer opens to a light filled dining room and great room with 10 foot coffered ceilings, exquisite details, and an elegant chef's kitchen equipped with Crownpoint custom cabinetry and top -of-the-line Wolf and Sub-Zero appliances. French doors lead to a covered porch overlooking the pool and yard. The second floor has 3 bedrooms each with a private bath and 9 foot ceilings. A separate staircase leads to a den with pull out sofa, wet-bar with ref/freezer and it's own full bath. Additional features include a full house generator, alarm system, and two smart tv's. This home is close proximity to Wades Beach and Mashomack Preserve.

Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023

Magical 1840's Cottage in Browns Hills with endless views across Orient Bay. Beautiful south facing garden abutting farm fields. Three bedrooms 1.5 baths, outdoor shower, deeded sound beach. A private, tranquil natural sanctuary in bucolic Orient. Offered July $15,000; Aug $15,000; Sept $8,000; year-round, furnished starting Sept $32,000/mo. Permit #0308.

2025 Rates: July $32,500, July-August $67,500 and August-Labor Day $35,000. Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!

Cedar Shake Ranch home on Goose Creek, ready for renters starting September 2022! Fully renovated, 4-bed, 2.5-bath. White & bright kitchen, living room, and dining, all in an open floor plan, perfect for entertaining. Move seamlessly through living space and out the sliding glass doors to a well-designed outdoor oasis. Built into a ipe deck is a heated swimming pool with lounge chairs and other seating areas surround. Plus, an outdoor shower and a big grassy yard with beautiful landscape, offering plenty of room for lawn games like badminton or corn hole. From the pool deck enjoy serene views of the water and wildlife. Kayak or stand up paddle board from the private dock or ride your bike to South Harbor Park beach or Croteaux Vineyards. Fully equipped home office/den space and exercise area with a Peloton bike in the basement. Available: Sept(not incl LBD):$12k, Oct:$8k, Nov 2022-April 2023:$4k/mo, May 2023(not incl MD):$8k, May 25, 2023 - end of June 2023:$18k, July 2023:$25k

Amazing North Fork home with heated salt water gunite pool located in Grandview Estates featuring 4 bedrooms (1st floor bedroom with ensuite, 2 ensuite guest bedroom on the second floor with 1 additional guest bedroom and guest bathroom) office/den also located on the second floor with a large sitting area and balcony at the landing of the second floor, large, finished basement with projection TV. Available October, November, and December for 2-week minimum period for $3,000 per week. Permit #0441.

Available 2024: May $9,500, Memorial Day-Labor Day $83,500, June $24,500, July $29,500, July-August $59,000, August-Labor Day $29,500, September $14,500, October $9,500. Available off season for $6,000 per month November 1, 2023, through April 31, 2024. Paradise along the Long Island Sound. This pristine and newly renovated home is a very unique offering w/ straight shot sunset views over the LI Sound and private beach access just 100 yards from the house down a sandy path through the Peconic Dunes. The home features an impressive primary en-suite overlooking the Sound, 2 guest bedrooms w/ shared hallway bathroom, and an additional flex room that can be used for sleeping quarters or as a remote home office. High soaring ceilings on the main floor allow for sun soaked exposure throughout the Great Room and impressive large Chef's kitchen. Truly a special property that will offer an authentic North Fork Summer experience! Permit# 0874.

Available 2024- MD-LD $53,500, May $6,000, June $12,500, July $19,500, July-August $41,000, August-LD $21,500, September $8,000, October $6,000: Escape to sweeping dunes along the Long Island Sound in the Hamlet of Peconic. This restored 1940's beach cottage offers charm, character, modern amenities and easy summer water-front living. The grounds are sprawling, incredibly private, will offer breath taking sunset and the ideal setting for summer stargazing. The interior features 3 bedrooms, 2 bathrooms, 2 living rooms and updated bathrooms and kitchen. Enjoy this serene setting nestled away along some of the North Fork's most desirable beach fronts.

Experience breathtaking views of Long Island Sound and Orient Point County Park from this spacious open-concept home. This beautifully updated 4-bedroom, 4-bathroom residence offers a private 20x40 heated saltwater in-ground pool and serene backyard. Host memorable gatherings in the spacious kitchen, perfect for indoor and outdoor dining. The expansive master suite boasts breathtaking views, a king-size bed, an office nook, dressing area, a full bathroom, and a private balcony. The lower level features a cozy sitting and entertainment room, an exercise room, a full bathroom, laundry facilities, a 2-car garage, and direct access to the pool and backyard. Enjoy easy access to the pristine sound beach, hiking trails, Orient State Park, and Duryeas restaurant. Located at the tip of Long Island, this exceptional home is perfect for anyone seeking coastal living with ample entertainment and relaxation space. Permit# 0234. Offered Apr $11,000; May $20,000; June $25,000; Sept 5-30 $25,000; Oct $20,000; Nov $15,000.

Also available Nov 1 - Apr 30 $36K This beautiful waterfront home in Sag Harbor is now available for rent for the first time. Sweeping views of the Little Narrows section of Sag Harbor abound and are afforded from many areas of the property. Highlights of the first floor include a large living and dining area that overlook the water, a separate kitchen, a charming study surrounded by windows, a guest room and hall bath. Upstairs is another guest room and bath and the primary suite, which has its own bath, a private veranda and is surrounded by windows and expansive water vistas. The backyard has a covered porch, an outdoor shower, a large deck and a long dock out to the bay, which is wonderful for boating, kayaking and even a swim. This waterfront gem is very close to Sag Harbor Village and its many wonderful parks, shops and restaurants. Rental Reg. # RP230721 Reg. Expires 6/15/2025 EH RR #: RP230721 Rental Terms: Winter Season: $33,000 Per Month Two Weeks: $35,000 August - Labor Day: $60,000

Charming 3-Bed, 2-Bath Home in Cutchogue's Creekfront Community Welcome to this newly renovated gem nestled in a serene Creekfront community in Cutchogue. This home boasts 3 spacious bedrooms and 2 modern baths, set on a sprawling property perfect for nature enthusiasts. The relaxed, sophisticated decor complements the spacious rooms, offering a perfect retreat from the hustle and bustle. A standout feature of this property is the large barn in the yard, ideal for storing bikes and summer recreational toys. The backyard patio provides a lovely setting for outdoor barbecues, while the spacious lawn offers plenty of room for playing and enjoying the outdoors. Inside, you'll find a brand new navy blue kitchen with stainless steel appliances, beautifully coupled with old-world built-in corner cabinets-a welcome mix of modern convenience and timeless charm. Enjoy stunning water views and the convenience of launching your boat, kayak, or paddle boards just at the end of the road. Cutchogue is home to many fine vineyards, perfect for sipping the fruits of the land, and farm-to-table dining experiences. Pristine beaches await for sunbathing and swimming, while quiet country roads are ideal for cycling and connecting with nature. The North Fork boasts plenty of restaurants offering fresh seafood in casual waterside settings. This is an ideal setting to relax and savor the beauty of nature. August: $11,000 September: $9,000

2024 Rates: September $15,000 and October $10,000. This property is a stunning waterfront home located on West Cove in the exclusive Nassau Point area. Offering breathtaking views of the Great Peconic Bay, Robins Island, and New Suffolk, this home exudes charm and sophistication. The main level boasts two spacious great rooms, an enclosed three-season room, an eat-in kitchen, a dining room, and a primary en-suite bedroom. The finished basement includes two additional bedrooms, a full bathroom, and a media room, while the second floor features two more bedrooms and another full bathroom. The property's grounds are beautifully landscaped and elevated, with a mahogany deck, stone patio, outdoor dining area, and stairs leading to a raised platform beach with a pergola, providing easy access to the Bay for a refreshing dip.

Newly Renovated Ranch Oasis in the Heart of the North Fork! Embrace the laid-back luxury of living in this stunning 3-bedroom, 2.5-bathroom ranch, completely renovated and move-in ready! This beautiful home is ideally situated in the central part of the North Fork, putting you within easy reach of everything this vibrant region has to offer. Stroll to charming shops, hop on public transportation to explore further, or indulge in fresh produce at farm stands - all just moments away. Craving a taste of the good life? World-renowned vineyards, delectable restaurants, and the picturesque Nassau Point Beach are all at your fingertips. This prime location also grants you access to all Southold town beaches, ensuring endless summer fun. Don't miss this opportunity to live in the heart of the North Fork's magic!