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Christmas Vacation Rentals on the North Fork

Christmas 2026 on the North Fork feels like a small-town holiday that happens to sit between two bays: fire trucks wrapped in lights rolling down Greenport’s Main Street, wineries lighting their own trees and quiet mornings on the Sound with nobody else around. Our North Fork homes stretch from Wading River and Riverhead out to Southold and East Marion, roughly two to two and a half hours from Midtown Manhattan.

The listings below only show the homes still open for Christmas week 2026 and for New Year’s Eve, so what you see is what you can actually book for the 2026 holidays. Several sit right on the water, a few have a fireplace or a private hot tub, and most of them welcome dogs, which makes the North Fork an easy place to bring the whole family home for the holidays.

North Fork Homes Available for Christmas 2026

Showing homes open from December 23 to 27, 2026. Change the dates to check other nights.

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Available for New Year’s Eve on the North Fork

Showing homes open from December 30, 2026 to January 2, 2027.

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What Guests Are Saying About Their North Fork Stay

East Marion 3BR | Fireplace, Deck, Beach Access

The house and grounds were perfect! We instantly felt at home and enjoyed our weekend there very much! You can walk to the beach, lavender fields, and the town and wineries are just a short ride. We look forward to returning to this delightful property and highly recommend!

Dunes Beach House: Hot Tub and Steps to Beach

We had a great experience! The house was big and comfortable, very clear and well equipped. Walking distance from the beach and 10 minutes driving from other beach locations. The place is extremely peaceful and relaxing. The host super responsive and helpful!!
Super, highly recommended!!

Diana Beach Retreat | Private Beach Near Vineyards

Darling, little cottage! Steps from the beach. Beach chairs, paddle boards and kayaks on site for use. Beautiful seating area outside for wine sipping evenings. Would definitely recommend staying here!

Waterfront Hot Tub Retreat w Kayaks | Kayak Point

We had a great stay with friends! The house was comfortable, with a beautiful view, and exactly as described. The common areas were perfect for being all together. The host was friendly and responsive, which made everything easy. Would definitely stay again!

Southold 3BR Waterfront Home | Dock, Kayaks, Creek Views

Had a wonderful time with/ family at this location. Truly enjoyed being together. The view was gorgeous, too. The restaurants were all great…Especially the Friskey Oyster in Greenport.

Sunset Perch: Heated Pool, Rooftop Deck, Walk to Beach

We had a wonderful couple of weeks here! The house was gorgeous, very well equipped (the kitchen in particular – a chef’s dream!), and in a perfect location with easy access to Greenport. We were traveling with a baby and were provided a highchair and travel crib. Luxury Beach Getaways was very responsive to all of our questions and helped us arrange for housekeeping and anything else we needed. Will definitely come again!

    Christmas on the North Fork 2026

    From Greenport to Riverhead, the North Fork’s holiday calendar is small-town and mostly free. Here is what to expect between Thanksgiving 2026 and New Year’s 2027, with each event’s expected 2026 date.

    Fire truck decorated with Christmas lights in a holiday parade at night
    Greenport’s Parade of Lights

    Greenport celebrates with the Greenport Fire Department’s Parade of Lights down Main Street, followed by the village tree lighting in Mitchell Park, carols and a visit from Santa and Mrs. Claus. For 2026 it is expected on Saturday, December 5, with the tree lighting around 4:30 p.m. When the weather cooperates, the Mitchell Park rink opens for skating, so pack gloves.

    Toy train with Santa in a Christmas holiday display
    Santa Arrives by Train

    The Railroad Museum of Long Island holds a free Holiday Open House at its Riverhead and Greenport locations, with Santa arriving by rail, model train displays and, in Riverhead, rides on the museum’s vintage World’s Fair train. For 2026, expect Riverhead on December 5 and 6 and Greenport on December 12 and 13, from 10:30 a.m. to 2 p.m. Confirm on the museum’s website. It is an easy morning out from any of our homes on either end of the Fork.

    Strings of holiday lights over an outdoor plaza with a Christmas tree
    Riverhead Holiday Light Show

    The Riverhead Holiday Light Show at Long Island Sports Park in Calverton is expected to run nightly from late November through December 31, 2026, from 5 to 9 p.m. Sunday to Friday and until 11 p.m. on Saturdays. It makes a simple evening outing, especially from our homes in Wading River, Riverhead and Jamesport, with plenty of time to get back for hot chocolate by the fire.

    Crowd gathered around a lit Christmas tree at dusk
    Village Tree Lightings

    Nearly every hamlet lights its own tree. The Southold Historical Museum’s Candlelight Tour and Tree Lighting is expected on Friday, November 27, 2026, from 3 to 6 p.m., with the tree lit at 5 p.m. Orient Beach State Park lights its tree in early December, expected Friday, December 4, at 5 p.m., the Mattituck Chamber of Commerce follows on an early December Friday evening, and in Cutchogue, Santa has been known to arrive by helicopter.

    Glass of red wine and a bottle beside a crackling fireplace
    Wineries in Winter

    Winter is the quiet season on the North Fork wine trail, which means no crowds at the tasting bar. Many wineries stay open on winter weekends, and some host their own holiday events, like Lenz Winery’s barrel tree lighting in Peconic, expected Saturday, December 5, 2026, at 4 p.m. Check each winery’s hours before you go, then head back to the house for dinner by the fire.

      Christmas & New Year’s on the North Fork 2026: What to Expect

      EventWhenWhereGood to Know
      Candlelight Tour and Tree LightingExpected Fri., Nov. 27, 2026, 3 to 6 p.m.Southold Historical Museum, SoutholdTree lit at 5 p.m.
      Parade of Lights and tree lightingExpected Sat., Dec. 5, 2026Main Street and Mitchell Park, GreenportTree lighting around 4:30 p.m., skating weather permitting
      Holiday Open HouseExpected Dec. 5–6 (Riverhead) and Dec. 12–13, 2026 (Greenport)Railroad Museum of Long IslandFree, Santa arrives by rail
      Riverhead Holiday Light ShowExpected late Nov. to Dec. 31, 2026Long Island Sports Park, CalvertonNightly from 5 p.m.
      New Year’s EveThursday, December 31, 2026Village restaurants and wineriesBook early, tables go fast
      December weatherAll monthNorth ForkCool, usually 30–45°F, very low crowds and the lowest rates of the year

      Frequently Asked Questions About Christmas on the North Fork

      What is there to do on the North Fork at Christmas?

      Plenty, all at a slower pace. Catch Greenport’s Parade of Lights and the Mitchell Park tree lighting, watch Santa arrive by train at the Railroad Museum of Long Island, see a hamlet tree lighting in Southold, Orient or Mattituck, and spend an afternoon at a winery that stays open in winter. Then come back to the house, light the fire and cook a holiday dinner.

      Is the North Fork worth visiting in the winter?

      Yes, if you like quiet. December brings cool weather, usually between 30 and 45°F, very low crowds and the lowest rates of the year. Beaches and farm roads are empty, the villages are decorated for the holidays, and many restaurants and shops stay open year-round, though some cut their winter hours.

      Are North Fork wineries open in the winter?

      Many are, mostly on weekends, and some host holiday events like barrel tree lightings. Hours change by season, so check each winery’s website before you go. Winter is actually one of the best times to taste, since you get more time with the staff and no summer crowds.

      How far is the North Fork from New York City?

      Plan for roughly 2 to 2.5 hours by car from Midtown Manhattan, depending on traffic. The Long Island Rail Road also runs to North Fork villages such as Mattituck, Southold and Greenport if you would rather leave the car at home.

      Can I bring my dog to the North Fork for the holidays?

      Yes. Most of our North Fork homes are pet friendly, so the dog can come along for Christmas too. Filter by pets in the search above or check the pet policy on each property page before you book.

      North Fork or the Hamptons for Christmas?

      The North Fork is farm stands, wineries and fire department parades, with a quieter, more local feel. The Hamptons trade that for village Main Streets, ocean beaches and a bit more polish. See our North Fork vacation rentals or our Hamptons Christmas rentals to compare. For holiday events on the South Fork, read our guide to Christmas in the Hamptons.

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