Woodbury Barber Shop

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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

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

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

Clued-up New Yorkers have slowly been turning their attention away from the Hamptons to this corner of countryside in Litchfield County. One step into this home, and we can see why they're making the swap. Set on six acres, this spot is a polished slice of serenity. Antiques from Europe fill the clapboard building, with Oushak carpets set on white oak floors. Gather the group for dinner under the chandeliers or curl up by the exposed brick fireplace come nightfall. The house has also been fully renovated. You'll find us in the sauna and steam shower, or making use of the studio with some yoga. Come summer, it's out to the decking for iced lemonade or soaks in the hot tub. When it’s time for something more serious, use the 16-foot quartz desk overlooking the garden. Your reward? Drinks at the wet bar.

Crop And Saddle

Once an 1890s carriage house, this home has been designed for country living for a small family. Low timber ceilings and hardwood floors retain the barn-like element, but instead of hay bales, you’ve got comfortable king-size beds for grown-ups and secret sleeping spots for kids in the mezzanine above the loft. Huge windows in the living room let in the sunshine, streaming through the trees, and in the evening, there’s a wood-burning stove to keep the chill at bay. The open-plan kitchen has a large double fridge, kitchen island and plenty of storage space for all the fresh goodies from the nearby farmer’s market. You’re in the middle of nature’s bounty here, after all. The farm is at the foot of the Catskills, away from it all, so you can spend your days immersed in the wilderness of hiking and biking trails. Stick close to home and wander the acres of farm grounds, through woodlands, past ponds or just the short dander to the farm’s swimming pool.    

Old Macdonald

Escape to the Western Catskills for a break surrounded by the rustling of leaves and the calls of birds. This architecturally significant A-frame cabin sits on a secluded plot among the tall trees – a clearing just for you. With nothing to distract you, here you'll be free to hike, spot wildlife, spend time together as a family or even write the novel you've been planning for years.

Inside, a towering vaulted ceiling and huge windows make this place feel bright and breezy whatever the time of year. All-white walls and Scandinavian styling are anything but rustic and the comfy modular sofa is the perfect place to snuggle in front of the pellet-burning stove on chilly evenings. One bedroom on the ground floor and another loft room make it suitable for a family or a couple of friends, and the pretty kitchen is surprisingly well equipped for cooking at home.

In the mornings, take your coffee out onto the deck and bask in the views and by night light the fire pit down in the garden for drinks under the stars. Just a ten-minute drive from Livingstone Manor, famous for its trendy breweries and excellent restaurants, you're in the heart of this bohemian area's foodie scene, with fly-fishing, hiking trails and more on your doorstep.

Reynard's Den

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

Fill your lungs with the scent of freshly chopped firewood as you step from the crisp Catskills mountain air into this gabled-roofed cottage. Whether you're a couple seeking stolen moments or a group of friends in search of calm, you'll find what you're looking for here. 

The wood-heady interiors cater to those in love with old-school design, particularly with the vintage wood-burning stove, record player and accompanying vinyl collection. On sunny days, a curl up on the hammock and listen to the babbling brook for hours on end – this simple pleasure is surely a tonic for the soul.

Keen hikers will no doubt be drawn to the nearby trails, taking you through the Catskill Mountains with the promise of spectacular vistas along the way. The town of Woodstock, made famous by the iconic 1969 music festival, is just a forty-minute drive away. Here you can load up on supplies and enjoy a hearty meal before heading back to your country retreat.

Cottontail Creek

Reminiscent of something from a Laura Ingalls Wilder novel, this picturesque cabin is a haven surrounded by peace and quiet and lush woodland. Although you can count on a serene stay here, you’re also just a five-minute drive from the quaint town of Old Chatham where you can find some local amenities, or a ten-minute drive from Chatham Town, which has several excellent restaurants and plenty of charming local shops. Perfect for a cosy couple or a small family, this home can welcome up to four guests, though two of them will have to sleep on the sofa bed. Spend your time reading on the porch, playing lawn games, and hiking in the area, before coming home to whip up a delicious meal in the fully equipped kitchen and settling down for a great night’s sleep in the King bed. Thanks to its picturesque setting, The Great Frontier is the ultimate escape for those who want to unwind and recharge in the comfort of nature.

The Great Frontier

Sitting alongside an enchanting creek, this cabin is a tranquil haven with a lot to offer. From the hot tub and wood fired sauna to the beautiful views, this is the perfect setting for a refreshing and romantic retreat. There’s also a barbecue, a pizza oven and a fire pit for magical night’s under the stars. Inside, the rooms are just as welcoming thanks to the cosy living room with a fire, the serene bedroom and the games room. Well behaved pets are welcome and you’ll find plenty to explore in the area. Follow nearby trails, discover charming towns and explore Lake Colgate and Hunter Mountain. 

The Creekside Cabin

This charming home is listed on the National Register of Historic Places, so character comes as standard here. Furnished with antique pieces and an eclectic art collection, it’s a house that’s packed with personality – from the cosy lounge and gourmet kitchen (ideal for entertaining and evenings in), to the chic bedrooms and bathrooms (complete with refined roll-top tubs). As for the location, nearby Albany offers restaurants, river cruises, and a thriving art scene, and makes a great base for exploring New York State.

Painted Shadows

A waterfront home in the Pocono Pines – yes please. Huge windows make it feel like you’re in the middle of the forest, though you’ll be able to pay for access to a premium club nearby, where you can golf, swim and play tennis – you get the peace of the wilderness with the amenities of a resort. This home also has its own dock on the pond, and you’ll have access to a canoe, boat and kayak to explore with. The hot tub, fire pit and barbecue make the deck all the more tempting, but if the weather isn’t playing ball there’s always the enclosed porch or fireplace. The games loft ensures teens will have nothing to complain about either. 

Lost In The Mountains

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Types

Book a stay in one of the best homes in Woodbury Barber Shop.

We selected the 916 homes worth renting in this location

Who's coming along?

Home spotlights in Woodbury Barber Shop

SUNFLOWER
SUMMER

LONG
POINT

COASTAL
RHAPSODY

We've selected the top 3% homes in Woodbury Barber Shop.

Most popular homes in Woodbury Barber Shop.

Crop And
Saddle

Old
Macdonald

Reynard's
Den

Sea
Aster

Cottontail
Creek

The Great
Frontier

The Creekside
Cabin

Painted
Shadows

Crop And
Saddle

Old
Macdonald

Reynard's
Den

Sea
Aster

Cottontail
Creek

The Great
Frontier

The Creekside
Cabin

Painted
Shadows

Lost In
The Mountains

Check rates and availability for Woodbury Barber Shop.

Book with Plum Guide.

Frequently Asked Questions

Book a stay in one of the best homes in Woodbury Barber Shop.

We selected the 916 homes worth renting in this location

Home spotlights in Woodbury Barber Shop

SUNFLOWERSUMMER

LONGPOINT

COASTALRHAPSODY

We've selected the top 3% homes in Woodbury Barber Shop.

Most popular homes in Woodbury Barber Shop.

Crop AndSaddle

OldMacdonald

Reynard'sDen

SeaAster

CottontailCreek

The GreatFrontier

The CreeksideCabin

PaintedShadows

Crop AndSaddle

OldMacdonald

Reynard'sDen

SeaAster

CottontailCreek

The GreatFrontier

The CreeksideCabin

PaintedShadows

Lost InThe Mountains

Check rates and availability for Woodbury Barber Shop.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Woodbury Barber Shop?

SUNFLOWER
SUMMER

LONG
POINT

COASTAL
RHAPSODY

Crop And
Saddle

Old
Macdonald

Reynard's
Den

Sea
Aster

Cottontail
Creek

The Great
Frontier

The Creekside
Cabin

Painted
Shadows

Crop And
Saddle

Old
Macdonald

Reynard's
Den

Sea
Aster

Cottontail
Creek

The Great
Frontier

The Creekside
Cabin

Painted
Shadows

Lost In
The Mountains