Southold

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Entertainment

Bathtub

Bathroom

Dishwasher

Microwave

Pod Coffee Machine

Freezer

Fridge

Kitchen

Kitchen & Dining

Washing Machine

Dryer

Bedroom & Laundry

Hot Tub

Wellness & Fitness

Wi-fi

Internet & Office

Fireplace

Air Conditioning

Central Heating

Heating & Cooling

Parking Available

Parking & Access

Balcony

Outdoor

Pets Allowed

Pets

Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence. The minimalist furniture has been carefully selected, merging with stone and wooden surfaces and creating a pleasant atmosphere. The ceilings are tall, the bedrooms are quiet, and there's lots of natural light, making the transition between indoors and outdoors seamless. A typical day in this home consists of lazy walks around the area, hanging out in the hammock, and curling up with a good book on the plush sofas. When you're ready to venture farther out, the beach is only a few steps away, so you can return home for a hearty lunch after a morning swimming and tanning session. There's lots to do in the area, from wine tastings to great independent restaurants, making it a great option for a foodie family.

Wander Inn

DVD Player

Sonos

DVD Library

Rain Shower

Hair Dryer

Cafetiere

Iron

Ironing Board

Swimming Pool

Desk / Workplace

Barbeque

Outdoor Audio

Garden

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

Ping Pong Table

Satellite / Cable TV

Sound System

Toiletries

Oven

Stove

Kitchen Utensils

Toaster

Blender

Coffee Maker

Cooking Essentials

Kettle

Black-Out Blinds

Hangers

Cleaning Products

Drying Rack

Extra Pillows and Blankets

Exercise Equipment

Laptop Friendly Workspace

Ceiling Fans

Free Parking On Premises

Free Parking On Street

Private Entrance

Patio / Terrace

Access to Beach

Beach Essentials

Outdoor Fireplace / Firepit

Outdoor Seating

Outdoor Shower

Sun Loungers / Beach Chairs

Resort Access

Nice to haves

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Smoke Detector

Other

Set across seven private acres on Shelter Island’s Menantic Peninsula, this waterside property epitomises tranquillity. Wake up to views on one of the home's two private balconies, before whipping up breakfast in the state-of-the-art kitchen and sipping your morning coffee as you paddle in the sea. Days here can be spent sunbathing on the private sandy beach, getting out on the water kayaking or paddle boarding, and honing your fishing and clamming skills. Come the evening, relax in the open-air Jacuzzi or get comfy in the large lounge, before retiring to one of four generous bedrooms.

Villa Menantic

Home Cinema Setup

Playground

Baby Bath

High Chair

Rice Maker

Cot / Crib

Bicycles

Private Pool

EV Charger

Balcony / Patio

Child Friendly

Anyone with a subscription to HBO might recognise The Old Life-Saving Station. The home has featured in both Lena Dunham’s Girls, and more recently, The Undoing, starring Hugh Grant and Nicole Kidman. Staying here puts you in elite company, and it’s not hard to see why. It’s a unique house. Dating all the way back to the 1800s, when it was built as a coastguard station for the Long Island Sound, it’s been renovated since, but with lots of care put into maintaining the farmhouse atmosphere and the vintage furniture. The home is set on three acres of land on the North Fork, and from the veranda, you can hear the waves lapping against the shore of the private beach. It’s a magical setting, perfect for long summer afternoons (and if the water is too cold, there’s a 50ft pool as well). Colder evenings bring their own charm, as the vast kitchen and living room come into play. The large table seats fourteen easily, so every night feels like a dinner party, while the crackling fire in the other room sets the scene for an evening curled up on the sofa, with a hot drink in hand.

The Old Life-Saving Station

Netflix

Board Games

Library of Books

Streaming Services

Changing Table

Children's Dinnerware

Espresso Machine

Baby Monitor

Laundry Supplies

Vacuum Cleaner

Printer

Bike Shed

Multiple Sets of Keys

Self Check-in / Check-out

Beach / Pool Towels

Fenced Garden

Fenced Property

Garden Games

Hammock

Herb Garden

Sun Umbrellas

Umbrellas

Welcome Hamper

Pet Bowls

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider. If hitting the many vintage stores in Sag Harbour isn’t on the cards, head out to explore the bay on one of the paddleboards or kayaks provided, by virtue of your own exclusive boat dock. Should that sound a little too energetic, you can also just take a dip in your private pool or luxuriate in the jacuzzi. The home is fresh, cool and contemporary while staying welcoming with warm rattan, bohemian touches, colourful books and art, and a rustic beachy feel. An aperitif on the pretty terrace is a must on balmy nights, or spend an evening around the fire with a movie in the cosy living room.

Long Point

Amazon Prime

Luxury Toiletries

Wine Cooler

Luxury Bedding

Throws

Breakfast Included

Just steps away from a private community beach, Borne Back was designed by its architect owner to provide a comfortable contemporary home in a perfectly quiet spot in the Hamptons. On a full acre plot next to Gardiner's Bay, it's surrounded by tall trees. Inside, it's modern, bright and relaxing, with subtle nods to its coastal location. Cook in the state-of-the-art kitchen, barbecue outside on the terrace or screen a movie on the home cinema setup. There's ample outdoor seating and a delightful, heated private pool to enjoy, and in the evenings, you could always treat your loved ones to a performance on the home's drumkit. We love the huge, sociable sofa in the living room and the first-floor sun terrace in particular but nothing beats the location of this place. A matter of metres from the beach and surrounded by quiet streets perfect for walks and bike rides, it's also within easy reach of several shops and restaurants.

Borne Back

Record Player

Sea Aster sits in an ideal spot for exploring beach and town life. Sag Harbor Main Street, with its restaurants, boutiques and artisan bakeries, is less than fifteen minutes’ walk away, and you can get to Haven’s Beach – a perfect spot to watch the sun set – in ten. The home has great dining and lounging areas, and the kitchen island makes the communal space even more open and social. With an ample sized garden, you get the calm and privacy that comes with the village farmhouse vibe while being at a handy distance from everything you’ll need. 


Sea Aster

Safe

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

Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning. It’s easy to see that Tom and Max have an eye for design. Light-filled, minimalist, and incredibly elegant, it’s the kind of place you look forward to coming home after perusing Sag Harbor or walking by the beach. Speaking of sandy stretches, you’re close to the village centre, giving you easy access to several beaches, along with lots of wonderful restaurants, shops, and bars.

The Whaler's Cottage

At the bottom of the garden, you’ve got direct access to the serene waters of Noyack Bay, with kayaks, paddleboards and bicycles provided by your host. It’s a fifteen to twenty-minute walk (or five-minute cycle) to the restaurants and grocery store of Noyack, just along the coast from Sag Harbour. Your host is a designer, and it’s evident in the big, light-filled spaces inside, especially the gourmet kitchen which you might recognise from several cooking shows on the Food Network. Apart from the grand lounge, there are family hideaways tucked away and a big games room and cinema for time together. We love the surf shack in the garden – a lofty summer house with a wood-burner for chilly evenings.  

Where the Wind Blows

A luxurious harbour-front villa overlooking the serene Noyack Bay, this home's stylish interior boasts elegance and sophistication. Huge, panoramic windows display the beautiful surroundings while flooding the space with light. An exquisite kitchen seamlessly blends the modern fixtures and fittings with a rustic style, pairing sleek marble-top counters with traditional brick and log walls. The large bedrooms have plush beds and window-walls, creating rejuvenating spaces, only furthered by the luxurious en-suite bathrooms featuring ocean-tiled walk-in showers. There is a serene, heated outdoor pool surrounded by lazing lounge areas, perfect for soaking up the summer’s sun. Located at the harbour's edge, the villa is moments away from delicious restaurants and quaint shops to explore. On more exciting days, you can take a short walk to the Northampton Colony Yacht Club for a day of sailing. 

Seascape

Mini Bar

Single-Level Home

Pack your bags and gather your favourite friends or family members, it's high time for a trip to the Hamptons. Just A Minute is a comfortable and modern home with easy access to Southhampton, where you can find everything you need from retail therapy to white sandy beaches. The home has a lived-in, comfortable feel, meaning you can settle right in without having to worry about a thing. The kitchen is fully equipped and the saltwater pool is ready for you to dive into. There's a fabulous social space at the heart of the home, with a cosy corner sofa, fireplace and bold artworks on the wall, and sets of sliding doors open it and the dining area out to the large deck – perfect for evening drinks in warm weather. Whether you want to spend the entirety of your trip at the house or explore the beautiful surrounding area, there is plenty to do on this small strip of Long Island. 

Just A Minute

Pool / Snooker Table

Ice Machine

Juicer

Heated Pool

Outdoor Pool

Desk

Workplace

Temperature Control

Buzzer / Wireless Intercom

Fenced Pool

Security Cameras

Escape the frenetic pace of daily life and revel in an unmissable opportunity to relax and recharge at this stunning Shelter Island getaway. Set on a quiet tree-lined street and just a ten-minute walk from the pebble-strewn seashore, the home is perfectly set up for family holidays and weekend retreats with friends.

Stepping inside, you could be forgiven for thinking you've been transported to the south of France, or the rolling Tuscan countryside. A gorgeous terracotta floor ties the open-plan layout together. The space includes a couple of seating areas, a well-equipped marble-topped kitchen and a dining table with seating for six.

Interior sliding doors allow for the creation of a self-contained king-size suite complete with a sitting room, while numerous glass doors line the walls, peeling back to reveal direct access to the large garden. Out here, you'll find plenty of comfortable seating areas and lots of green space for children to run around and play endless games of table tennis.

Three further bedrooms are situated on the top floor – all are well illuminated thanks to overhead skylights and windows that afford garden and golf course views.

For days out, pack up the beach chairs and parasols from the garage and make your way to the nearest pebble beach, a quarter of a mile away. Alternatively, saddle up on the included bikes and cycle fifteen minutes into town for family-friendly restaurants, ice cream parlours, and even a couple of upmarket eateries.



Straight Down the Middle

Games Console

Accessible Parking

Outdoor Kitchen

Stair Gates

A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light. It's the ideal family pad, especially with a lounge fit for kids (complete with a pool table) in the basement and a workout room (including a Peloton bike) that fitness buffs will appreciate. And there's no denying that there's plenty of space to spread out. Two main suites have parents and in-laws covered, the sunroom is an excellent spot to enjoy a cup of tea in the afternoons and the kitchen is a dream to cook in, with glossy tiles, high-end appliances and all the crockery you'll need.

Make your way outside and while away sunny days by the pool. Come evening, fire up the barbecue and tuck into an alfresco feast before gathering around the fire pit on the Adirondack chairs to watch the stars come out. The peaceful scenery is made even better by the excellent location. This home is tucked away on a tree-lined cul-de-sac that backs up to a nature preserve, with walking trails right on your doorstep. It's an easy seven-minute drive to the stores, restaurants and coffee shops in East Hampton, while Two Mile Hollow Beach and other stretches of sandy coastline are just eleven minutes away.

Summer Fridays

Minutes away from East Hampton Village, this beautiful Sag Harbor home is ideal for sun worshippers and golfers alike. The Sag Harbor Golf Course is a stone's throw, and Havens Beach, among others, is reachable by car in minutes. Or you can make the most of sunshine days from home, where the private pool, ample seating, grill and wraparound balcony awaits. The third bedroom hosts four guests on two double beds, but the room is large and comfortable, and there's plenty of space throughout to stretch out. It's a home the whole family will enjoy as you experience the best of The Hamptons. 

Harbor Hymn 

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck. Luckily, the home’s bright, colourful design lives up to its surroundings, with patterned throws and bedspreads, quirky artwork and unique furniture. From the moment you step foot inside, you'll feel right at home. There are 1.5 acres of land to explore out the back, with plenty of options for alfresco dining, whether you choose to relax with a barbecue under the wisteria or socialise on the patio. On hot summer days, go for a swim in the crystal clear pool, or lie back with a book on a sun lounger nearby. As if this wasn't enough, it’s also perfectly located for making the most of Springs, with the sea just a five-minute cycle away, and coastal walks and surf beaches within easy reach. On Saturdays, amble over to the Farmer’s Market to purchase fresh produce to whip up a feast. All in all, this is a delightful stay for young families or a group of old friends coming together. 

Sunflower Summer

This quintessential clapboard home in Sag Harbor is sure to pique the interest of travellers looking for a relaxing stay in the Hamptons. With its close proximity to the coast, including Haven's beach, the home is conveniently located for exploring the area. Taking it easy at home is also a tempting option here with a private pool, garden and outdoor shower. Inside, the rooms have been thoughtfully curated for families and remote workers with a dedicated home office space and a sleek kitchen and dining area that opens out onto the patio. Note that the third bedroom is only suitable for one adult or two younger children. 

Cruising The Coast

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space. Downstairs, the living space is all about its designer leather sofa and chairs, as well as a large glass dining table. There's an excellent kitchen, with everything you'll need to cook at home, and even a den upstairs, complete with a sofa and office desk for working remotely. Outdoors, the huge deck is the star of the show, with seating areas, an alfresco dining spot, a cabana and a swimming pool. It's just a ten-minute drive to Westhampton beach to paddle in the Atlantic Ocean or visit one of the many excellent bars or restaurants.

Long Island Iced Tea

Underfloor Heating

If you’re looking for all the charm of a country cottage with the space and grandeur of a manor house, this is the spot for you. It’s a four-minute stroll to the vast stretch of sand at Long Beach and a six-minute drive sees you in the heart of the pretty village of Sag Harbor. Or, you could while away the days in the privacy of the leafy-green backyard. Out here, you’ve got a pristine swimming pool set in the wooden deck and a shower to wash sandy feet after a trip to the beach.

Inside, it’s a mix of crisp white walls and ink-black accents. Gabled, white-wash ceilings give that country cottage aesthetic and floor-to-ceiling windows fill the place with sunlight. Boho beanbag chairs and pot plants add a rustic touch to the living room and the sleek, modern kitchen is fit for gourmet meals. Underfloor heating in the plush bathrooms is another nice touch. 

The Striped Sea Bass

Bathrobes

Heated Towel Rail

Trash Compactor

Wine Cellar

Access to Gym / Spa

Jacuzzi

Sauna

Sauna / Steam Room

Tennis Court

Rooftop Terrace

If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court. And while there’s everything you could need to enjoy the great outdoors, the rooms are just as inviting with a home theatre, a sauna, a wine cellar and plenty of socialising space across the living and dining rooms. You might find it hard to leave this peaceful sanctuary, but it’s just a short stroll to the nearest restaurants and shops.


Coastal Rhapsody

Projector

Electricity Adaptors

Step-Free Access

This riverfront home is the kind of getaway we dream of every day. The infinity pool and views of the Hudson River are magnificent – just imagine how calming it is to wake up to views of this calibre every day. Inside, it feels incredibly warm and welcoming, making it perfect for family gatherings and spending time with your loved ones. The screened porch was extremely inviting, it’s the kind of place that inspires you to slow down. While there’s a lot to love about this home, we couldn’t get enough of the garden – manicured and green, it also boasts an infinity pool.

Jewel on the Hudson

Private Washing Machine

Private Dryer

Nestled in the woodlands, this cabin provides cosy comfort and stylish charm. The outdoor area is the perfect place to keep toasty by the fire and eat delicious meals. Guests looking for outdoor adventures can explore the surrounding landscape by foot or by bike, and couples and small groups will enjoy the romantic views and secluded location. The covered porch is the perfect spot for reading and bathing in sunlight, while the patio is ideal come summertime. Other features to admire are the unique ornaments collected by the lovely host, Minetta.

Burnt Sienna

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866,  is steeped in history and rural charm. Full of wooden touches and warm accents, the home has been thoughtfully designed for relaxed, rural living. When you sip your morning coffee, you’ll have views of horses in the rolling fields. Later on, gather the group for meals by the traditional wood-burning stove between walks along the brooks and journeys into Wahconah Falls State Park. The home is secluded enough to let you disconnect surrounded by natural splendour, but there’s no shortage of entertainment to be found. Famous for its culture just as much as its landscape, The Berkshires are just as robust with art exhibitions and literary events as they are with rolling hills. Even Moby Dick is said to have been written somewhere amidst these very mountains. If you’re looking for a place on the east coast where the famous goes to truly hide, this is it. 


River Song

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