Dutchess County

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Set between the Hudson River and the Catskill Mountains, this spectacular 18th-century farmhouse is full of upstate New York charm. Nestled in 35 acres of secluded woodland, the house is a breath of fresh air less than two hours’ drive from the hustle and bustle of Manhattan. Step inside and you will instantly notice the owners’ keen aesthetic eye and attention to detail. Each room is bursting with character, and full of antique furniture, contemporary art, and vintage trinkets.  

The distinctive living room has a large wood burning fireplace and plenty of games for the kids. There is also a sun room which is perfect for relaxing in with a book. The farmhouse kitchen is well equipped with a range of appliances and cooking essentials. Upstairs, the palatial main suite comes with an office for remote working, a living area with its own fireplace and coffee station, and a claw-footed bathtub in the bathroom. The second and third bedroom have their own unique charm, and there is also a junior bedroom with plenty of toys and books for the little ones.

Outside, there is plenty to do and see. You can pick apples in autumn from your woodland (there are wellies at the house if it’s muddy!), go skiing and sledding in winter, or follow one of the nature trails leading to the creek. The village of Saugerties is a six-minute drive away, where you’ll find a grocery store, a farmer’s market and some laid back restaurants. 

The Dutch Farmhouse

Nature meets luxury at this stunning Berkshire Mountain retreat. Just twenty minutes from Great Barrington and with hiking trails all around, this home is an idyllic escape from the hustle and bustle. Set in 167 private acres, this home has everything you could wish for. Admire mountain views from the hot tub on the sun deck, unwind in the steam room, and enjoy a tipple from the main bedroom’s wine bar. Your host can arrange for a chef to whip up feasts in the chef’s kitchen and order custom kegs for the kegerator. The open-concept living areas – with floor-to-ceiling windows – make socialising a dream. This home is perfect for a large family gathering. 

The Berkshires Splendour

This Martha’s Vineyard-inspired house in nestled in the village of Bellport. You can enjoy leisurely strolls to the nearest restaurants and you’ll have access to a private beach if your stay is longer than a week. Back at home, there’s a swimming pool for blissful swims, a barbecue for alfresco dining and a fire-pit for magical evenings under the stars. Inside, the rooms have been thoughtfully designed to inspire ease and relaxation. There’s a desk for remote workers and exercise equipment is provided to energise your stay. 

Sunset Heart

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

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 home's architecture, interiors and colourful prints all share a mid-century modern style, but its woodland surroundings are more Hansel and Gretel than Gilbert and George. In a tiny hamlet in upstate New York, it’s surrounded by mountains, lakes and forest – great for skiers, hikers and wild swimmers alike. The home has several standout features but we love the double-height living area, with its huge windows and cosy fireplace. The galleried landing has a desk in case you need to keep one eye on work while you're away, and the huge deck has a gas barbecue for those long lazy lunches outdoors. While its statement design pieces add interest, it's a homely place too, with a bedroom set up for children, logs provided for the fire, and plenty of books to pick through on the shelves. Just minutes from a choice of state parks, forests, orchards, and wineries, your days will be filled with outdoor adventures – and all just an easy drive from the city.


Art & Nature

Originally built in the 1870s, this farmhouse has been added to over time to create a sociable family home. Inside, original details such as exposed wooden beams and large sash windows are complemented by vintage furniture and traditional furnishings, while a bar is ideal for evening cocktails. But you’re likely to spend most of your time outside, exploring the ten acres of land, enjoying a drink outside on the deck, taking some time to reflect at the koi pond, or gathering around the outdoor fireplace after the sun goes down. There’s also a natural pool fed by a mountain stream, which you can swim in, surrounded by frogs, water lilies and other aquatic life.

Doric Detail

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

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

This beautiful old clapboard church has been turned into a woodland retreat like no other, where deer regularly stroll among the trees. Just outside Woodstock, there are craft beer breweries, farm shops and mom and pop coffee shops a short drive away, and trails into the Catskills are all around. From the outside, this home still looks like it holds Sunday Service, tucked in 1.5 acres of forest. 
Arched, stained-glass windows throw rainbows of light into the living room and what was once the altar is now a cosy nook for a wood-burning stove, framed by the wooden mantel from a famous Broadway theatre. The kitchen is fully-equipped with spices, ingredients, utensils and everything you'll need to prepare a hearty home-cooked meal. What was once the Sunday School room is now a lavish bedroom and just beneath the belltower, you’ll find a reading nook for lazy days, plus a range of games to keep everyone entertained. Outside, you’ll find a barbecue grill and seating on the patio, and a hammock to enjoy the sounds of the forest with a gentle sway. This is one home that really needs to be seen to be believed. 
Woodstock STR Permit No: 21N239

Woodland Hymnal

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

A nature lover's dream atop a 100-acre historic farm in North Stonington, away from the hustle and bustle of everyday life. This home offers a one-of-a-kind stay – spend your mornings in the fresh air helping the hosts tend to the farm animals in the tranquil setting to feel at one with nature – from feeding chickens and collecting eggs to brushing the horses and rooster calls here and there, but it's all part of the experience.

The home itself is chic and stylish, yet homey. Mornings are best spent sipping coffee on your patio while admiring the mountain and pasture vistas of your host's Texas longhorn cattle and horses. The living area is accented with slate grey throughout, while the brown provides an earthy sense to make you feel even more connected to your environment, and is ideal for cosying up after a long day of wandering through the unending greenery. We love that the second bedroom has an art studio for letting your creativity flow, where you can paint a stunning picture of the grounds you're staying on, as well as skylights, so you can fall asleep beneath the stars.

When you want to splash around in the sea, take a twenty-minute trip to Misquamicut State Beach, fantastic for the kids to spend a day at the beach while you sit back and relax. Alternatively, drive twenty minutes to the beautiful seaport village of Mystic and explore the foodie haven featuring the area's local meats, organic produce and seafood for a tantalising supper. Stop by Jonathan Edwards winery on the way to pick up a bottle of Pinot Grigio to enjoy back at the house around the fire pit with blankets wrapped around, or check out the dedicated bar area in the living room and craft your own cocktails. There's plenty of North Stonington's rich agricultural heritage to explore nearby, including cattle ranches, organic farms and vineyards (fifteen minutes away by car). 

Mystic Countryside Farm

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Book a stay in one of the best homes in Dutchess County.

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Home spotlights in Dutchess County

THE DUTCH
FARMHOUSE

THE BERKSHIRES
SPLENDOUR

SUNSET
HEART

We've selected the top 3% homes in Dutchess County.

Most popular homes in Dutchess County.

The Captain's
House

Sunflower
Summer

Art &
Nature

Doric
Detail

Long Story
Short

The
Edge

Woodland
Hymnal

Dahlia
Darling

The Captain's
House

Sunflower
Summer

Art &
Nature

Doric
Detail

Long Story
Short

The
Edge

Woodland
Hymnal

Dahlia
Darling

Mystic Countryside
Farm

Check rates and availability for Dutchess County.

Book with Plum Guide.

Frequently Asked Questions

Book a stay in one of the best homes in Dutchess County.

Home spotlights in Dutchess County

THE DUTCHFARMHOUSE

THE BERKSHIRESSPLENDOUR

SUNSETHEART

We've selected the top 3% homes in Dutchess County.

Most popular homes in Dutchess County.

The Captain'sHouse

SunflowerSummer

Art &Nature

DoricDetail

Long StoryShort

TheEdge

WoodlandHymnal

DahliaDarling

The Captain'sHouse

SunflowerSummer

Art &Nature

DoricDetail

Long StoryShort

TheEdge

WoodlandHymnal

DahliaDarling

Mystic CountrysideFarm

Check rates and availability for Dutchess County.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Dutchess County?

THE DUTCH
FARMHOUSE

THE BERKSHIRES
SPLENDOUR

SUNSET
HEART

The Captain's
House

Sunflower
Summer

Art &
Nature

Doric
Detail

Long Story
Short

The
Edge

Woodland
Hymnal

Dahlia
Darling

The Captain's
House

Sunflower
Summer

Art &
Nature

Doric
Detail

Long Story
Short

The
Edge

Woodland
Hymnal

Dahlia
Darling

Mystic Countryside
Farm