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North Fork Dream Home: Choose the perfect summer rental now

A small red cottage with a front porch, white trim, and two chairs sits on a well-kept grassy lawn surrounded by trees and shrubs under a clear blue sky.
Patrick Trzcienski
February 5, 2025
A small red cottage with a front porch, white trim, and two chairs sits on a well-kept grassy lawn surrounded by trees and shrubs under a clear blue sky.

Okay, so you just put away the holiday decor and are working away on those new year resolutions—at least those you haven’t given up on yet. If one of those is finding a place to rest your head this summer, let us help! Here’s a preview of some rental homes coming on line for the season:

Single-story house with a sloped roof, large front windows, stone steps, and a paved driveway, surrounded by trees and a landscaped yard.

2905 Private 1 Road, East Marion
If woodsy is your jam, this four-bedroom in a 3.6-acre forest clearing offers plenty of green space, a spacious yard and a generous deck overlooking the 20′ x 45′ heated pool. Its adjacency to preserved land guarantees privacy a bit off the beaten patch. The large eat-in kitchen has plenty of space for casual dining and food prep if you’re in entertaining mode, and the separate dining room and large deck offer even more options. The living room and family room are both anchored by large wood-burning fireplaces for gathering around the hearth on chilly evenings. The home comes with Parks District beach rights to Truman’s Beach.

Rates: Memorial Day–Labor Day: $40,000; June: $10,000; July: $15,000. Weekly rental considered at $3,750 per week with two-week minimum.

Modern house with an upper deck overlooking a rectangular pool, surrounded by outdoor seating and a fire table with drinks and a tray on top.

27840 Route 25, Orient
Moving from woods to field, this three-bedroom modern house with glass walls offers bucolic living in the country side. Set on 2.2 acres, this recently renovated home features tasteful and creative modern organic décor, farmland views, a large pool, firepit and conversation area and a vine-entwined pergola for alfresco dining ala Tuscany or France. Close to local farm stands, you’ll have plenty of room to cook up a bounty in the sleek kitchen and serve it on the deck overlooking the yard. Numerous rooms for relaxing, including a pretty glassed-in sunroom. Close to beaches and golfing, country clubs and parks.

Rates: $38,000 for Aug. 16-29; inquire about other availability.

Rectangular outdoor swimming pool with clear blue water surrounded by green grass, next to a red house with white trim under a partly cloudy sky.

1800 Westphalia Road, Mattituck
This turn of the 19th-century barn (1900) on .7 acres has been converted into a chic five-bedroom country compound with a pool and plenty of room for lawn games. Sited in a waterfront enclave, access to Mattituck Inlet is close by for swimming and paddling. The large kitchen offers counter and eat-in dining, in addition to the formal dining room seating 12. A wood-burning fireplace in the living room will take care of chilly evenings, and the farm vibe is echoed in warm rustic touches such as exposed-wood ceiling beams. The lower level has a media room.

Rates: Memorial Day to Labor Day: $50,000; June: $15,000; July: $20,000

Small red cottage with white trim, a covered front porch with chairs, surrounded by green grass, trees, and bushes under a clear blue sky.

80 Park Road, Riverhead
If you’re looking for a solo getaway or maybe something for just the two of you, this charismatic cottage on .28 acres might be for you. Once a country store in what is now the Reeves Park Beach Community, the circa 1940s cutie has been renovated into a one-bedroom getaway with  a loft and kitchen. Wall shelves in the open living-dining room evoke the house’s former life as a store and wainscoting walls add authentic charm. With a queen-sized sleeper sofa and a king-sized bed in the bedroom, it accommodates four.

Rates: June–August, $6,000 per month.

Modern building entrance with a curved white wall, tall pillars, a partially open wooden door, and landscaped greenery under a covered walkway.

15105 Oregon Road, Cutchogue
Maybe your philosophy is go big or go home: if so, then this six-bedroom, seven-bath resort-styled compound provides ample room for family and friends to enjoy a summer in the country. Set on five acres in the vineyards, this 7,000-square-foot house offers floor-to-ceiling windows with views of the vines, a large roof deck, a covered dining area that seats 20+. The expansive entertainment courtyard features a gunite heated pool and firepit. Numerous spaces inside for entertaining, including family and living rooms with fireplaces.

Rates: $80K per month, with either monthly or two-week availability.

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