North Fork

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Mere steps from the beach, this four-bedroom farmhouse sleeps ten and is ideal for a large family getaway. Rustic it may be, but the interiors don’t skimp on style – white walls and pops of colour lend it a modern Scandinavian vibe. An open-plan kitchen with a Carrara marble island and KitchenAid mixer make meal prep a cinch – get everyone together to bake a cake. A travel crib, highchair and changing pad are provided for the littlest family members. 

The Captain's House

This classically designed North Fork home is in the grounds of a working vineyard, so it should certainly appeal to wine lovers. You’re encouraged to take a tour of the production facility while you’re here, with a cheeky complimentary glass for every guest. Inside, the old blends seamlessly with the new, so historic features are set off by the sleek lines of modern furnishings. There’s a generous kitchen complete with antique wine press, while the patio is the perfect spot for enjoying a morning coffee or evening glass of wine. Just a short drive from the heart of Jamestown, you’re perfectly placed to explore other nearby vineyards and farms, not to mention all the dining and shopping opportunities in the area. Beach bums will be happy here too as there are plenty to choose from, both locally and further afield.

Vine Ripened

The summer retreat for Manhattan’s wealthy elite, the vibe of the Hamptons couldn’t be further from New York’s chaotic urban sprawl. And if you’re looking for the ultimate in serenity and tranquility, this idyllic beach house is for you. Every element of this cottage has been thoughtfully considered to make the most of its seafront location on Long Island’s North Fork. Inside, the whitewashed colour scheme extends to every room, creating a soft, calming atmosphere. In the open kitchen/living room, vast windows and glass sliding doors welcome in the dune-studded view and ocean breeze. In the bedrooms, pressed white linen lies on pale-wooden bed frames, with driftwood adorning the minimalist dressing tables. And as relaxed as you’ll feel inside, just wait until you step outside. Where the decked terrace ends, the beach begins, meaning you’re just a couple of barefoot steps from the gently rolling waves. Bliss.

Salty kiss

Whether you're eight or eighty, this Colonial-style home has got something to keep you entertained. Gather the group together in the cream-toned downstairs living room – with an electric fireplace to keep warm – for debriefs of the day, before peeling off into the myriads of rooms. Big kids can organise competitions in the games room, with hours of fun on the pool table, air hockey table, retro arcade machines and more. And if you've still got energy to burn, hit up the home's gym to pump some iron. Rest and relaxation comes in equal measure – pour yourself a drink in the upstairs living room's bar, or head out to the decking to nab the double sun lounger. Nightfall doesn't mean the end of activity, with a seven-person hot tub and an outdoor firepit to keep you toasty as your gang congregates under the stars. Everything you need is here, but if you want to venture out, Southampton Village is nearby and a hive of upmarket boutiques and restaurants.

The Apple Picker's Perch

This European-inspired villa ticks all the boxes for an indulgent stay while feeling close to nature. Tucked into woodland and surrounded by manicured lawns, it features a stepping-stone path leading to a private beach and boat so you can set sail on the gentle waters of Noyack Bay. Inside, a nautical theme takes centre stage, with propellers, porthole mirrors and boat models as mainstays. Those who are a dab hand at cooking will love the professional-grade appliances in the large kitchen. After cooking, have your feast alfresco on the deck by the wrap-around pool, and as the day draws to an end, take to the bay with a bottle of bubbles and settle in for an unforgettable sunset.

Port & Starboard

That all-American, wood clad, cosily furnished Hamptons home you've been dreaming of? We've found it. With its picture-perfect setting, its traditional (yet stylish) interiors, beautiful terrace and sprawling country-style kitchen, it's got everything you could want for a stay on the illustrious Shelter Island. Bedrooms are grand, with antique dressers and each of the cosy living rooms are packed with seaside-themes trinkets and a library's-worth of bookshelves. The sprawling grounds are perfectly manicured and hidden away at the back is the dreamiest of swimming pools, surrounded by seagrasses and created to look like a wild pond – heaven. Long summer nights can be spent enjoying drinks in the garden as you leave the grill masters to fire up dinner – a state of the art sound system will help you create the perfect setting. Sea lovers need only wander five minutes from the home to find a peaceful nearby beach, perfect for sandy strolls in the morning or evening. 

All American

The more nautically inclined of holidaymakers will love this waterfront home in Greenport, but even those with only a passing appreciation of boating won't fail to be wowed by the property and its peaceful location.

The interior is strikingly contemporary, with a wealth of sleek surfaces, eye-catching decorations and chic furnishings — not to mention the floating staircase. That being said, there are plenty of home comforts present too, including a fireplace and a fitness room full of equipment down in the basement.

And that's before we've even got around to mentioning what lies outside. Whether you choose to lounge on the balcony or out on the deck, it's simply lovely to listen to the water flowing by as the sun sets overhead. The presence of a barbecue and fire pit gives you an excuse to stay out even longer.

As well as a private bay from which you can embark upon an adventure along the nearby Peconic River, the restaurants and shops in the centre of Greenport only take five minutes to reach by car, as does Truman's Beach in the opposite direction.

Meet Me By The River

Just steps from the beach with views across Peconic Bay, this home brings ease and comfort to coastal living. Bikes are provided for exploring and it’s just a short drive to the restaurants and shops of Southold. Ocean lovers will appreciate the paddle boards and canoes, while those in search of pure relaxation will find perfect contentment lazing on the deck. Inside, the rooms are child friendly (you’ll just need to watch the stairs), plus there’s a range of extra services your host can organise to make your stay feel truly special – including private chefs and massage treatments. 

Well & Happy

A renovated barn complete with a heated outdoor pool, all within walking distance of Bridgehampton. This charming home ticks all the boxes, and you can even drive to the beach in a matter of minutes. Inside there's a classical theme, dripping with antiques and vintage paintings. The double height living space is flooded with sunlight, and musical types can tinkle on the ivories at the home's grand piano. Outside, in the one-and-a-half acre grounds, there’s a large pool to splash around in, generous lawn for family games, and a fire pit for those nights when you just can’t bear the day to end – some s’mores and a hot chocolate should do the trick. You’ll find plenty to keep you busy nearby too. Take your pick from the local beaches, go wine tasting at the nearby vineyard or do some high-end shopping.

Beaming Smiles

Summering in the Hamptons has long been the preserve of New York's elite, and this home is heavy on nostalgia. Just the shape of it is enough to illicit a sentimental smile about years gone by. On the banks of Mecox Bay, there are water views from nearly every angle. And while it's nice to gaze at from the terrace, the pool, and even the games room, the best place to enjoy the waterfront is the home's own little boathouse. Summer days here are spent outdoors, whether it's swimming, cycling or playing tennis – and there are spectator seats if you're feeling particularly confident about your backhand. In the evenings, cocktails can be prepared at the oak bar and meals cooked in the chef's kitchen. When you’re done, organise card games in front of the open fire, just like we did in the good old days.

Elderberry Estate

This Hamptons home does island life the modern way. In the mornings, hit up the local farmers’ markets and seafood shops. Then, in the evenings, cook your fresh fish in the state-of-the-art open kitchen. From the inter-connected Sonos surround sound system to the marble fireplace, vibrant art-works and comfortable furnishings – it's the fine details that set this home apart from the rest.

We love how close this home is to the beaches but when you’ve had enough of salty water, take a dip in your private heated pool. The beautifully landscaped patio garden surrounded by the local greenary offers a peaceful spot to enjoy some much-needed vitamin D. Come rain or shine, this spot presents a quiet sanctuary away from city life – and one that you can enjoy by spending quality time together as a group. 

When you are ready to venture out, spend your days cycling around the island. With scenic spots all around, Shelter Island invites you to switch off and reconnect with nature through time in a new environment. Ahh, we can smell the fresh air already. 


Ahoy There

Nestled in a copse of trees, this fabulous home packs on the wow factor with striking good looks and a bold all-white interior. Just a short drive from Bridgehampton and the pristine Atlantic beaches, it's the ideal country retreat if you enjoy the finer things in life. Take a morning dip in the pool, or just relax with a coffee on the expansive deck, while those with a musical gift can sit down at the piano in the living space. Nearby, explore historic museums in Water Mill, and return home with local produce from the market for an evening barbecue. With your holiday soundtrack on the Sonos speakers, grab a bottle from the wine cooler and settle down on the lounge chairs outside to admire a perfect Hamptons sunset. 

A Ray of Light

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