Vacation Rentals By Owner In Orient, NY

Beautiful custom build newly renovated North Fork Home. Backyard oasis with pool, brand new hot tub, shower and fire pit. Walkable private beach. Across the street from the Cross Sound Ferry. Driving distance to Orient Point State Park, Restaurants, Wineries and much more.

Serene East End Oasis

Orient, New York, United States

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Exceptional(8)

$1607.66

Charming, updated historic farmhouse set on 1.6 acres in Orient Point - perfect for a large family vacation. Fenced in yard and deep woods at the back of the property create a quiet and private space. Heated saltwater gunite outdoor pool with hot tub and poolside outdoor kitchen with grill and stainless-steel sink. Spacious eat-in kitchen with dining room table and separate outdoor pergola perfect for entertaining. Spacious living room with wood burning fireplace and separate den for kids to play. Mudroom with full washer and dryer. Cross the street for drinks or dinner at Duryea's and the entrance to Orient Beach State Park (bike (10 min), run or drive into the park itself), 10 min walk to the beaches of Orient Point County Park, 20 min bike / 5 min drive to historic Orient town center and Truman's Beach (beach guest pass available). brTown of Southold Rental Permit #724

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient, New York, United States

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Exceptional(1)

$1646.85

Welcome to our spacious and stylish beach home - providing an incredibly comfortable and rejuvenating experience that will leave you wishing your stay would never end. This sun drenched and open floor plan home delivers a true indoor / outdoor living experience, with abundant space for entertaining and relaxation, manicured outdoor grounds and gardens secluded by tall hedges, featuring Adirondack chairs, an oversized hammock, an outdoor dining area and BBQ, and a gorgeous outdoor shower built upon a giant slab of slate. This beautiful property is just steps away from a private community beach that offers expansive views of the Long Island, safe swimming for children, and breathtaking nightly sunsets. brbrThis conveniently located property is just minutes to the Cross Sound Ferry to Connecticut, sight seeing and fishing charters, the Orient Point County Park and Orient Beach State Park, the Shelter Island Ferry, and the many restaurants and shops in nearby Greenport and neighboring hamlets. Taking the Shelter Island North and South Ferries will have you in Sag Harbor within an hour and on to the beaches and villages of the Hamptons. The North Fork is also home to many of the best vineyards and breweries in New York. br*There is private parking for 3 vehicles on the property

Gorgeous North Fork Farmhouse with Private Beach Rights

Orient, New York, United States

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Exceptional(20)

$856.91

The Lane House offers the perfect idyllic getaway with a private community beach access you won't need a car for. brbr12 minutes to Greenport Village, 20 minutes to Peconic Pickleball courts, 3 minutes from Cross Sound Ferry, 2 minutes to Orient Beach State Park, and near many vineyards, farm stands, and countless other attractions.brbrOrient Point is located at the eastern tip of the North Fork offering a bucolic escape like no other surrounded by rural wine country, farmstands aplenty, and some of the best restaurants on the East End.brbrThe Lane House is a cozy four bedroom home plus office. 3 of the bedrooms and office are in the second floor, and one bedroom with a queen bed on the main level. brbrOutdoor shower after your beach day. Every bed is outfitted with down comforters, percale sheets, and plush pillows. The open floor plan makes for great group entertaining. The kitchen is stocked with all the things you need for cooking those great meals. The deck in the rear is ready for grilling and dining on those warmer nights. Don't forget to use the wood burning fireplace to create those memorable cozy fall evenings after apple picking, or coming back from wineries. The private community beach is within walking distance from the house. brbrLove to bike or run Head on over to the Orient Beach State Park for a 2.5 mile ride/run to the 363 acres park while surrounded by the perfectly preserved salt marshes and red cedar forest to the beautiful beach, playground, picnic area, and hiking. Or just take a bike ride right outside and enjoy the quiet community.brbrPeconic Pickleball Court - free courts with nets 2580 Peconic LnbrbrOrient Point County Park - incredible views of the Sound for fishing, hiking, or bikingbrbrOrient Beach State Park - 363 acre park with beach, playground, kayak rentals, food, picnic area, hiking, and more.brbrOrient Point Ferry - ferry (with or without your car) to ConnecticutbrbrOld Schoolhouse Park - small park in East Marion with one tennis court, and playgroundbrbrThe Candy Man - handmade candies, and chocolates!brbrLavender by The Bay - locally owned lavender farmbrbrLatham's Farmstand - located in OrientbrbrSep's Farmstand - located in East MarionbrbrNorth Fork Table & InnbrbrKontokosta Winery - 62 acre waterfront with gorgeous views of the Long Island Sound and vineyardbrbrBedell CellarsbrbrFrisky OysterbrbrAmerican BeechbrbrFork & AnchorbrbrLittle Creek Oyster Farm - shuck your own oystersbrbrNoah'sbrbrIce SkatingbrbrRoller SkatingbrbrGreenport VillagebrbrSouthold Fish MarketbrbrHarbes Orchard

The Lane House | Private Beach Escape

Orient, New York, United States

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Exceptional(61)

$1052.73

For a rejuvenating time with loved ones, this gorgeous waterfront home is waiting for you at the tip of rustic Windward Road. With four bedrooms, you can bring your whole family for a relaxing length of time that you desire for your vacation. This home features a princess-style bedroom with a four-poster queen bed and beach facing balcony. The master bedroom with a king bed, has a direct-beach facing balcony and its own bathroom. This room has a modern free standing tub and separate shower. Another bedroom with queen bed, also has a balcony, and has a bathroom to include a shower. The fourth bedroom with queen bed also has a balcony. There is a central hall bathroom to include a tub. Three bedrooms include a desk. All bedrooms have either direct, or side view of the water. Each bedroom has a television. The hallway is a sitting area with a couch. br brThe main floor features a spacious living room with two sofas and sitting lounge chairs, centrally located fireplace with marble surround, and television. The English styled kitchen is centrally located on the floor, and it is fully stocked with several sets of flatware, full line of utensils and accessories, and we include spices for the guests needs. The countertops are emerald green granite. The charismatic European style dining room sits ten people and like the rest of the floor, it features stunning views of the LI Sound. A very spacious family room to the east of the kitchen will fill your morning with the beauty of sunrise and warm colors. Here you can use the exercise bike or hand weights, yoga mat, as well as having books and board games if you want some quieter moments. On either side of the dining area you have sliding doors to access the spacious patio which faces the water and perfect for sunrise and sunset viewing. Patio table with umbrella and patio furniture will be waiting for you to relax and enjoy. Can you smell the grill sizzling Our guests will have access to the washing machine and dryer. The basement is not part of this agreement, as it is utilised by the owner at times. br brThe guests will enjoy the comforts of home in a luxurious, relaxing setting. The location is the highlight for vacationing at this beautiful home. Minutes by car from the scenic Duryea’s Restaurant, from the Orient Beach State Park, farm stands and even a regionally renowned candy store and historical society. This Orient home is also a quick drive from the historic village of Greenport with its famous carousel, the restaurants that feature fresh seafood and locally grown produce, antique and souvenir shops, art galleries and professional amenities that bring a touch of urban sophistication to the tip of the North Fork. Here, you can access the ferry to Shelter island. brFrom Orient Point, you can take the ferry to Connecticut. brLovely place to enjoy views, tapestry of stars at night, fishing, swimming, kayaks, bird watching, local wineries and restaurants. We comply with 14 minimum stay Suffolk County regulation.

Beachfront vacation dream house on Long Island Sound.

Orient, New York, United States

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Exceptional(60)

$932.71

Relax and Unwind at Our Stunning Waterfront Home with Long Island Sound ViewsbrExperience the ultimate coastal getaway at our beautiful Orient Point waterfront retreat. Enjoy serene walks along the private beach or take in breathtaking views of the Long Island Sound from every corner of the house.brbrThe spacious Great Room offers ample seating with cozy couches and chairs, perfect for relaxing while watching your favorite shows on the large flat-screen TV. Whether you're spending the day by the outdoor pool (just steps away from the living room) or enjoying the warmth of the fireplace, this inviting space is designed for comfort and relaxation.brbrThe fully equipped kitchen boasts top-of-the-line appliances and is stocked with everything you need to prepare delicious family meals.brbrMaster Suite (Upstairs)brRetreat to your private oasis in the master suite, complete with a king-size bed and an exclusive soundside balcony, perfect for sipping morning coffee while watching the sunrise. The suite also features a TV, mini-fridge, coffee maker, double vanity sinks, a walk-in shower, and a large jetted tub for ultimate relaxation.brbrDownstairs BedroomsbrThe two inviting downstairs bedrooms each offer a queen-size bed with the option to add twin beds to accommodate your family’s needs. These rooms provide ample space for comfort and relaxation.brbrWhether you're enjoying the tranquil views, taking a dip in the pool, or spending quality time with family in the spacious living areas, our home offers everything you need for a memorable vacation.brbrbr br

Orient Point Waterfront Home – Private Beach & Stunning Views

Orient, New York, United States

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Exceptional(5)

$2227.87

Brand New Farmhouse private beach and Inground pool in Orient Point. 4 bedroom and 4.5 baths. Each Bedroom has private en suite Bath!! Custom Kitchen, Pool, outside bbq Private bay Beach Assoc and across street from Ocean and State park. Ferry is 3 minute walk!! Greenport 10 min drive

Private Beach and Ing Pool! New build 4 bed 4.5 bth Farmhouse! Chefs kitchen

Orient, New York, United States

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$2073.36

Freshly renovated Orient Village designer gem with heated pool on a private, one acre vineyard.3.5 bedrooms, 3 bathrooms with massive common area. Guest Room/Den/Office/Playspace with pullout couch. Brand new top-of-the-line chef's kitchen with deck overlooking vineyard. Screened-in porch. 2 minute walk to private beach & historic Orient Village. Heated Pool, Central air, Washer/dryer, high speed internet, TVs with streaming video, gas BBQ. Great layout for a family + grandparents/nanny. Don't miss out on the perfect North Fork escape. Book now!

Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town

Orient, New York, United States

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Exceptional(99)

$679.79

Rental Permit #1073 brOur Little House on the Prairie home is located on the picturesque North Fork of Long Island in the peaceful hamlet of Orient with wildlife including deer, hawks, turkeys and rabbits. This quaint property offers a comfortable and cozy stay for guests with front and back covered patios, a Weber gas grill, patio furniture, fire table, central air conditioning, dishwasher, washer/dryer, Netflix, and WiFi. Less than 1 mile from both Sound and Bay beaches which have spectacular views. Home is located 3 miles from Orient State Beach, a 350 acre peninsula with 10 miles of beach front and the Cross Sound Ferry to Mohegan Sun, Foxwoods and Mystic Seaport, CT. 5 miles from the historic harbor village of Greenport featuring unique shops, & boutiques, delicious restaurants, ice cream shops, museum, movie theater, antique carousal, Island Ends Golf Course and the ferry to Shelter Island. Wineries & Breweries throughout the region open year-round for tours and tasting. Kontokosta Winery 4.5 miles from home. Locally grown fruit and vegetables at farm stands. Pickleball Court at Oyster Ponds School .3 miles from home. brBeautiful Fall weather for pumpkin and apple picking, hayrides, roasted corn, and mazes.brNO Cleaning Fees brNon-Shedding Hypoallergenic dogs allowed (limit one)brNo cats allowed. No smoking or candle burning inside home

Charming Country Home sits on a 3-acre property in Bucolic Orient.

Orient, New York, United States

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Exceptional(24)

$387.21

BAYSIDE COTTAGE is available from 3 April 2026. Minimum rental period is two weeks, which can be split over two stays. Discounts available for monthly and longer rental periods.brbrThe Real Thing... the lull of lapping waves, private beach, on the Bay... Simple, plain, authentic, uncorrupted and unadorned “Summer of ‘42” beach cottage for those discerning few who recognize and appreciate the difference. Located in Orient’s National Historic District, and formerly part of Bay House Cottages. Adjacent to Orient Yacht Club. 2-minute walk to Orient Village and Oysterponds Historical Society. Deep-draft boat mooring available.brbrUpstairs: 3 Bedrooms, Bathroom, Bayfront BalconybrDownstairs: Parlor (w/Franklin Stove as heat source), Kitchen, BathroombrbrInside: Simple, Plain, Authentic & UncorruptedbrOutside: Covered Porch, Shower, Picket-fenced yard, WW1 MonumentbrbrPhotos provide views of exterior and surroundings of Bayside Cottage, as well as an interior “walk through” and some items from the historical archives.

Cottage

Orient Village — Historic Bayfront Cottage — 2026 Season

Orient, New York, United States

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Exceptional(21)

$1923.46

This family owned home was built in 2001. Set in a quiet, residential development the home is on Long Island Sound with picturesque views of the Orient Point Light house. It is walking distance from the Orient Point Ferry. After the spectacular sunset the Ferry will silently glide across the dark water providing a beautiful display of lights. Be our guest and enjoy the relaxing, quiet atmosphere as a family or as couples. Although Greenport is only 8 miles away, you may never want to leave!

Orient Point Family Waterfront Home

Orient, New York, United States

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Exceptional(29)

$639.8

14 Night MinimumbrbrWe offer Boat Cruises as part of your stay, or separately. Please feel free to reach out for more information.brbr1,100 Square Foot house with 400 square foot deck in the backyard. House is part of community with rights to a private beach with a private barbecue/recreation area only a few minutes walk away.brbr14nt minbrbr10 minute walk to Orient Beach State Park which has the following activities: Biking, Canoeing/Kayaking, Fishing, Food , Public Grills, Hiking, Nature Trails, Pavilions, Picnic Tables, Playgrounds, Playing Fields, Recreational Programs, Showers, Paddle Boarding, Swimming Beach, Wind surfing, etc. brbr10 minute walk to the Cross Sound Ferry Terminal which offers ferry to New London, CT as well as a High Speed Jet to CT Casinos.brbr10 minute walk to the Orient by the Sea Marina and Restaurant, which serves food on the waterfront as well as chartered fishing trips.brbrLess than 15 minute drive from Greenport Village.brbrLess than 45 minutes from a great shopping experience at the renown Riverhead outlets and malls.brbrLess than 20 drive from world famous North Fork wineries. brbrLocal buses with services to local towns as well express bus service to New York City from Cross Sound Ferry Terminal.brbrHigh Speed Wireless Internet as well as Cable TV in every room. Large flat screen in Living Room with Netflix, Xbox 360.brbrBedroom 1:brQueen Size bed brFlat screen TV with Cable and WiFibrFull size ClosetbrA/C unit and Ceiling Fan for the cooler days.brbrbrBedroom 2:brQueen Size bed brFlat screen TV with Cable and WiFibrFull size closetbrA/C unitbrbrBedroom 3:brBunk Bed with Full Size bed on the bottom and twin size ontopbrFlat screen TV with Cable and WiFibrFull size closetbrbrbrLiving Room:brLarge Flat Screen TV with Cable with Xbox 360 (With 2 remotes and games) and PS3 with access to Netflix accountbrHigh Speed WiFibrComputer Desk areabrLarge wood Burning FireplacebrbrPlease note, rates are for 4 adults. Additional adults are subject to additional fees.brRenters must be 29 and older, absolutely no parties and loud noise will be tolerated. brMinimum stay is 14 nights.

Private Getaway - corner Home with rights to private beach - Tip of North Fork

Orient, New York, United States

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$534.53

Quaint 2 bedroom cottage. Family friendly. In ground, salt water, heated pool with lawn chairs. Outdoor deck with seating. BBQ grill. Walk to private beach. Walking distance to scenic Orient by the Sea Restaurant. Bike ride to Orient Beach State Park.brHistoric Maritime Greenport - 15 Min. Drive, and all Norfolk wineries are nearby.brbrNo parties, Smoking outside allowed, not inside.- only small pets. Thank you.

Orient Point Cottage with Private Beach

Orient, New York, United States

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Most popular vacation rentals in Orient

$387.21

Cottage

Orient Village — Historic Bayfront Cottage — 2026 Season

Orient, New York, United States

Bed

Bath

Sleeps

$679.79

Charming Country Home sits on a 3-acre property in Bucolic Orient.

Orient, New York, United States

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Bath

Sleeps

$1256.75

Villa

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

Orient, New York, United States

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Sleeps

$1607.66

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient, New York, United States

Bed

Bath

Sleeps

$1646.85

Gorgeous North Fork Farmhouse with Private Beach Rights

Orient, New York, United States

Bed

Bath

Sleeps

$2227.87

Private Beach and Ing Pool! New build 4 bed 4.5 bth Farmhouse! Chefs kitchen

Orient, New York, United States

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Bath

Sleeps

$639.80

Private Getaway - corner Home with rights to private beach - Tip of North Fork

Orient, New York, United States

Bed

Bath

Sleeps

$856.91

The Lane House | Private Beach Escape

Orient, New York, United States

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Bath

Sleeps

$1052.73

Beachfront vacation dream house on Long Island Sound.

Orient, New York, United States

Bed

Bath

Sleeps

$932.71