Vacation rentals in Nassau Point

Waterfront Beach Cottage

Renovated New Suffolk Waterfront Beach Cottage steps from water/beach/restaurants & more w/ water views from practically every window in the heart of the most special neighborhood in the north fork. Perfect for families with twn over full bunks, pvt mstr, grill, outdr shower and new kitchen. Bonus room has comfy couches & sunset views. Dine al fresco with water views or stroll to restaurants, apple picking or famous New Suffolk beach. Minutes from everything your vacation could need, year round.

Nassau Point, North Fork Home w/ Pool

Whether you are looking for lots of outdoor space for the kids to explore, bike, play at the beach or splash around in the pool OR you are looking to explore all of the 38 Vineyards along Long Islands, this house is perfect for you. Open kitchen, dining and living space which then opens up to the deck and pool. 4 bedrooms, sleeping 8 comfortably. Two of the bedrooms are connected with a thru-door. Gated swimming pool. Minutes from the local sandy beach. Rental Permit: HMT24-00101 14-Day minimum

Beautiful 1930s 4 bed 3 bath! Walk to Beach

Beautiful 1930s fully renovated cottage with 4 gorgeous bedrooms & 3 full baths. Spacious outdoor living space including an outdoor shower & fire pit. 1 block from a beautiful life guarded, sandy bay beach. Relax with the family at this peaceful place to stay in exclusive Fleets Neck and close to multiple spectacular wineries, breweries, farms, shopping outlets and worldclass restaurants. Stunning waterscapes abound! Enjoy a country retreat in a slice of heaven! Southold town permit 1137

Hamptons Waterfront Getaway – Stylish & Serene

Waterfront Luxury Retreat in Sag Harbor. As featured in Vogue, Mansion Global, and Homeworthy. This serene designer home offers direct bay access for kayaking and paddle boarding, plus a private path to Clam Island for peaceful walks and beach picnics. Enjoy a gourmet kitchen with Viking and Sub-Zero appliances, spa-like en-suite baths, and plush bedding. Minutes to bay beaches and Sag Harbor village—your private escape awaits. Ideal for romantic getaways, relaxing weeks, or a summer reset.

Renovated 2-Bedroom Cottage on the North Fork

Serenity awaits as you step into this totally renovated Cottage. The property is perfectly located in the heart of Long Island's Wine Country. Centered on the North Fork this home allows you to explore all that there is to offer…. antique shops, restaurants, vineyards, breweries, farm stands and the beautiful Causeway Beach is just steps from this home. The home is newly renovated with a new kitchen, appliances, new bathroom, outdoor gas grill, fire pit and a beautiful screened in porch.

Barefoot Bliss | Quiet Family Retreat Heated Pool

Welcome to your Hamptons retreat. This bright single-level home sits in a quiet neighborhood just minutes from Main Street and the ocean. The private fenced yard overlooks a peaceful nature preserve and features a heated pool (June–Sept, heating available for a fee), hot tub, outdoor fireplace, and outdoor shower—perfect after a beach day. Family-friendly amenities include a sandbox, toys, crib, and highchair, with a separate safety fence surrounding the pool for added peace of mind.

Sag Harbor Chic Modern Cottage

Escape to this charming Sag Harbor cottage, featuring three inviting bedrooms, two full baths, a cozy living room, light and airy sunroom, and a sun-filled kitchen and dining area. Relax in the delightful sunroom or unwind in the beautifully landscaped private garden, complete with a bluestone patio and a picturesque pergola. Perfectly situated just minutes from pristine bay and ocean beaches, marinas, scenic nature preserves, farm stands, acclaimed restaurants, and boutique shopping.

Luxury by the Sea!!

Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. This home is beautifully designed with too many architectural details to list. Property is fully furnished 🛋 with no detail spared . Open floor plan, spacious great room with gas fire place and flat screen, gourmet eat 🍝 in kitchen with large island is a wonderful place to entertain 🥂. Brand new washer/dryer, butlers pantry and mud room. Where the country meets the sea 🌊

Waterfront Home with Private Dock & Beach

This charming waterfront home is the ideal getaway for the active family with the Hamptons' largest natural 'saline pool' (the Peconic Bay) just footsteps away. This home easily sleeps 7 - with 3 bedrooms and 3 separate kids' sleeping cabins. You can jump on our standup paddle board right off our private dock, jog along wide stretches of pebble beach, have a swim race to our floating swim platform or simply relax in the hammock. 2 bathrooms indoors and 1 private outdoor shower,

Enjoy a relaxing getaway to the North Fork

One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

New Suffolk Beach Cottage 1 | North Fork

Cottage 1 sits in a beautifully maintained garden compound just one minute from private sandy beaches on Peconic Bay. Quaint New Suffolk is among the most coveted hamlets with notable beaches on the North Fork. Come for spring blossoms, summer beaches or autumn harvest. Enjoy wine tastings at nearby world class vineyards and best of market locally grown produce, farm to table dining, fresh fish markets, orchards and miles of scenic vineyards.