Woodbury

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When you want to get away from the hustle and bustle, this New Lebanon home is the perfect choice. You’ll not only leave the hectic city behind – stepping through the doors feels a little like stepping back in time. 

This home is 150 years old, and was a Shaker workshop. It’s on the National Registry of Historic Places and has been beautifully renovated to emphasise its history. You’ll find Shaker details like wide board pine floors, and the paint colours used are all accurate to the era. The history of a former Shaker settlement is evident at every turn, but modern convenience has also been considered. Everything you might wish for has been taken care of, so your stay will be comfortable as can be. 

The home is stunning. Elegance and historic charm come together in every stylistic detail. There’s plenty of room for everyone to gather together, whether it’s for elaborate meals prepared in the attractive kitchen, or around the fire pit for marshmallows and spooky stories. 

You can look forward to mesmerising views of the Lebanon Valley, and can explore the area on foot. There’s a forest and meadow that are ideal for hiking, as well as a nearby pond and waterfall to visit. The remoteness makes this a wonderful base for a relaxing stay. Though when you feel adventure calling, you can easily answer by driving to Berkshire and the Hudson Valley, where you’ll find plenty of restaurants, shops, and theatres. 


Ode to the Past

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

For the ultimate Montauk escape with style and character in abundance, this fisherman's cottage has you covered. Flamingo-pink shutters and the front door set the scene for a stay that's thoughtfully stylish, charming and quirky – a blend of boho and rustic that's sophisticated and easy to love. The white-beamed ceiling, pink accents and mix of raw wood and design pieces makes for a look you'll want to replicate in your own home. This cottage just feels very at home in this neighbourhood, with a colourful living room drenched in natural light and a surf-shack motif in the bedroom, complete with surfboards and dreamcatchers adorning the walls. If the personal touches didn't already make this home, the location definitely does – you're a five-minute walk from popular eateries and Downtown Montauk, not to mention Fort Pond, the train station and nearby beach.

Long Story Short

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

Nestled within 26 acres of beautiful grounds, this private estate welcomes you to an immersive retreat in Rhinebeck. From the indoor sauna and hot tub to the calm rooms, every detail has been considered to inspire optimum relaxation. There is also a yoga and fitness studio as well as a pool table and a wet bar – ensuring entertainment options for the whole group. Remote workers will appreciate the dedicated desk space, while we imagine everyone will love gathering by the fire for games or movie nights. From here, you can follow hiking trails straight from the door and it’s less than a fifteen-minute drive to Hyde Park and Rhinebeck.

Rise with the Sun

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

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

This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods. Floor-to-ceiling windows make full use of the region’s scenery, and sliding doors out onto a deck mean you can practically reach out and touch the pines – you can even listen to the rushing waters of the creek from here. Modern and stylish, the design here isn't trying to outshine the views, with wood floors, white walls and a Scandi feel to its furnishings. Two of the bedrooms are on the top floor and have such great views across the canopy you'll think you're staying in a treehouse, while immaculate bathrooms are outfitted with marble, lava stone and Italian Porcelanosa tiles. If you can drag yourself away, head out on hikes, explore the nearby farm shops, or book a meal at a local restaurant – there are several within a short drive. But we recommend making your way to the home's little campfire site, with some hot chocolate and marshmallows, for an evening you'll never forget.

The Edge

Indulge yourself in the natural world at this sun-drenched home, with plenty of space for friends and family indoors and out. You'll find toys and games along with free children's sledges for enjoying the snow, and kids will love the bunk beds. The outdoor fire pit offers cosy evenings under the stars, and the babbling brook at the end of the 5-acre garden brings you that bit closer to nature. Just minutes away you'll find Bethel Woods, the home of the original Woodstock, and the town of Bethel along with the picturesque Lake Superior State Park are an easy drive away.

Dahlia Darling

An understated colonial-style home is the perfect setting for a Northeastern getaway. It's reminiscent of a family heirloom, with history seeping through the walls. Situated on a bluff with views of the Connecticut shoreline, the home sits atop sprawling private acres dotted with centuries-old trees. A typical day here will take you straight back to the carefree life of childhood – gather in the kitchen for pancakes before slipping on your sandals to walk down the lawns to your very own private beach, before spending the evening playing games around the fireplace in a cosy living room. Choose a new bedtime read from the home's library or brainstorm your own novel in the study – perfect for remote workers. Port Jefferson is only a short twelve-minute drive away, and you’d be remiss not to stop at the farmers market and bring back fresh produce to cook, reminding you of the pleasures of a simpler life. 

Hamlet

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

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

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

We selected the 914 homes worth renting in this location

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Home spotlights in Woodbury

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CROP AND
SADDLE

LONG STORY
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We've selected the top 3% homes in Woodbury.

Most popular homes in Woodbury.

Long Island
Iced Tea

Rise with
the Sun

Cottontail
Creek

Jewel on
the Hudson

The
Edge

Dahlia
Darling

Hamlet

River
Song

Long Island
Iced Tea

Rise with
the Sun

Cottontail
Creek

Jewel on
the Hudson

The
Edge

Dahlia
Darling

Hamlet

River
Song

Borne
Back

Check rates and availability for Woodbury.

Book with Plum Guide.

Frequently Asked Questions

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

We selected the 914 homes worth renting in this location

Home spotlights in Woodbury

ODE TOTHE PAST

CROP ANDSADDLE

LONG STORYSHORT

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

Most popular homes in Woodbury.

Long IslandIced Tea

Rise withthe Sun

CottontailCreek

Jewel onthe Hudson

TheEdge

DahliaDarling

Hamlet

RiverSong

Long IslandIced Tea

Rise withthe Sun

CottontailCreek

Jewel onthe Hudson

TheEdge

DahliaDarling

Hamlet

RiverSong

BorneBack

Check rates and availability for Woodbury.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Woodbury?

ODE TO
THE PAST

CROP AND
SADDLE

LONG STORY
SHORT

Long Island
Iced Tea

Rise with
the Sun

Cottontail
Creek

Jewel on
the Hudson

The
Edge

Dahlia
Darling

River
Song

Long Island
Iced Tea

Rise with
the Sun

Cottontail
Creek

Jewel on
the Hudson

The
Edge

Dahlia
Darling

River
Song

Borne
Back