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Vacation Rentals in South Jamesport, NY

Tucked along the gentle curve of Peconic Bay between Jamesport and Aquebogue, South Jamesport is one of the North Fork’s quietest and most rewarding corners. A small waterfront hamlet within the Town of Riverhead, it offers the kind of bay-facing calm that draws people back summer after summer: uncrowded beaches, honest local character, and easy access to everything the North Fork does best.

South Jamesport sits at a comfortable remove from the crowds while remaining close to everything worth doing. The bay is steps away. The North Fork wine trail begins practically at your door. Sound Avenue’s legendary farm stands are a short drive in either direction, and Riverhead’s waterfront is just minutes west for when you want a little more energy around you. This is the North Fork the way it used to be: unhurried, unpretentious, and genuinely beautiful.

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What Guests Are Saying About Their Jamesport Stay

Jamesport Cottage | Walk to Peconic Bay, Fire Pit

Amazing location, everything we wanted and more. Highly recommended!

Jamesport Cottage | Walk to Peconic Bay, Fire Pit

Cute cottage. Fully equipped and ready for BBQ in the big back yard.Comfortably sleeps 6. 2 beds upstairs. The large basement with a trundle and separate additional bedroom and full bath.Professional, easy check in and out. Woule definitely use again

Jamesport Cottage | Walk to Peconic Bay, Fire Pit

Second time for our family. Wonderful, comfortable, cozy home, nice backyard, quiet with enough space for everyone. Proactive hosts. Recommend.

Jamesport Cottage | Walk to Peconic Bay, Fire Pit

Great home for a group of friends or a family traveling to the east end of Long Island. Great proximity to the area wineries and the Hamptons. Would definitely stay here again!

Jamesport Cottage | Walk to Peconic Bay, Fire Pit

My elderly mom was in between moves, and wanted to stay near her shop in Jamesport. This little gem of a home fit the bill, and more. The location, on a sweet, private road, steps to the beach- made every day special. The kitchen gets the morning sun, the house is well suited for easy living, on one floor, with a level back yard, and a spacious basement is all we needed and we enjoyed the charming house.

Jamesport Cottage | Walk to Peconic Bay, Fire Pit

We had a lovely time at this cottage. Close to the wineries and lots of great restaurants. Great yard and patio to sit outside and relax.

    Make the Most of South Jamesport

    The bay, the wine trail, the farm stands, and some of the North Fork’s best towns are all within easy reach of South Jamesport. Days here have a way of filling themselves up before you’ve finished your morning coffee.

    South Jamesport Beach

    The hamlet’s bay beach is the anchor of any stay here: a calm, shallow stretch of Peconic Bay that’s ideal for swimming, paddleboarding, and long morning walks with coffee in hand. The water is warm, the crowds are light, and the views across the bay toward the South Fork are the kind you end up photographing every single day. Return to your Luxury Beach Getaway home in the afternoon and you’ll find the day has a natural rhythm all its own.

    On the Water

    Peconic Bay wraps around South Jamesport in a way that makes every kind of water activity feel within reach. Launch a kayak or paddleboard from the bay shore, try clamming in the shallow flats, or cast a line from the beach at dusk when the stripers start to run. For a more organized excursion, fishing charters operate out of nearby Jamesport and Mattituck Creek. After a full day on the water, your Luxury Beach Getaway home is exactly where you want to be.

    The Wine Trail

    The North Fork wine trail is practically at the front door in South Jamesport. Jamesport Vineyards, one of the oldest wineries on the North Fork, is just minutes away and worth an afternoon of your time. Palmer Vineyards in Aquebogue is nearby as well, and the trail extends east through Cutchogue and Peconic for a full day of tasting room exploration. Pick up a few bottles to bring back to your Luxury Beach Getaway home and you’ll have a very good evening.

    Day Trips Worth Taking

    Riverhead is just minutes west and worth exploring for its waterfront revitalization, independent dining scene, and the Long Island Aquarium, a reliable hit with families traveling with kids. Head east and you’ll find Jamesport village, Mattituck, and eventually Greenport, each with its own distinct character and dining worth the drive. Your Luxury Beach Getaway home in South Jamesport sits at an ideal midpoint, easy to leave and easy to come back to.

      Frequently Asked Questions

      Where exactly is South Jamesport on the North Fork?

      South Jamesport is a hamlet in the Town of Riverhead, located along the north shore of Peconic Bay. It sits between Aquebogue to the west and Jamesport to the east, roughly in the middle of the North Fork’s length and within easy reach of nearly every town from Riverhead to Greenport.

      How do I get to South Jamesport from New York City?

      By car, expect roughly an hour and forty-five minutes to two hours from Midtown Manhattan depending on traffic, making it one of the more accessible North Fork destinations. The Long Island Rail Road serves Riverhead, a short drive away, and seasonal jitney service connects to various North Fork stops.

      Are South Jamesport vacation rentals good for families?

      Absolutely. Our properties are designed for comfortable, unhurried stays. They work equally well for couples, families, and groups of friends who want to mix beach days with relaxed evenings in a well-appointed home.

      What should we pack? 

      Layers are always a good idea, as coastal weather shifts quickly. In summer, bring beach gear and comfortable walking shoes. In fall and winter, add warm layers and a rain jacket. A smart outfit or two is worth packing for dinner out in the villages.