Canaan

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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

Surrounded by acres of forest, flowing streams, waterfalls and historic ruins, this little cottage welcomes you to experience the natural beauty of the Berkshire mountains. 

Located within a former Shaker settlement, there’s an abundance of charm and character here. From the antiques and art to the snug furnishings and personal touches, the owners have designed this space to enrich your stay with warmth and ease. So whether you’re here for an adventurous escape or for total relaxation, this home welcomes you to enjoy it all in the heart of New Lebanon.

Snuggle up in front of the fire, get cosy with a book, admire the views and gather for heartwarming evenings around the kitchen table. However you spend your time here, every moment promises to be enhanced by the unique spirit of this location. 

From here, it’s just a five-minute drive to the restaurants, shops and antique stores of New Lebanon. And for explorations further afield, you’ll find easy access to the charming villages of New England as well as the Hudson Valley.

A Little Love Note

There are some homes that simply capture your heart from the moment you arrive. And we won’t be surprised if it’s love at first sight when you see this charming Colonial saltbox house. 

Nestled within the Litchfield Hills and surrounded by acres of beautiful gardens, ponds and walking trails, this is the perfect setting to connect with the beauty of nature. Inside, the exposed beams and wooden floors fill this home with a calming presence. It’s the kind of space that inspires you to slow down and savour the luxurious details that make this home unique. And whether you're spending a cosy morning by the fire, cooking in the kitchen or out on the patio, it’s easy to settle in and make this space your own. 

Outside, you’ll find 170 acres of majestic countryside to roam and explore. Wander over bridges, embrace wild swimming and simply soak in the stunning views across the rolling hills. The centre of Litchfield is just a ten–minute drive away where you’ll find a wonderful selection of restaurants and shops for any amenities you might need.

The Golden Dawn

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

Immersed in a sanctuary of trees, this rustic cabin invites you to enjoy a serene retreat in the Catskill Mountains. 

Set across five acres and just a six-minute drive from the charming town of Roscoe, there’s everything you could need to feel inspired and renewed by the majestic beauty of this special environment. 

From the atmospheric views to the exceptional styling, every detail has been considered to fill your stay with freedom and ease. And from the moment of arrival, you’ll want to pause and savour the calming simplicity of this space. High ceilings and large windows create a wonderful sense of lightness, while the seamless blend of natural tones reflects the beauty of the surroundings. Step outside and you’ll discover the expansive deck is ideally positioned for a quiet morning coffee, or later with magical evening drinks and stargazing by the welcoming fire pit. 

Follow the mountain road and you’ll find the bustling town of Livingston Manor is just a fifteen-minute drive away. There’s a great selection of cafes, shops and restaurants here, while you’ll also find an abundance of opportunities for hiking and fishing – Roscoe is known as Trout Town, USA. 

Wherever the day takes you, this home provides a constant sense of sanctuary – the perfect setting to light a fire, put on a record and savour the timeless charm of mountain living. 

The Mountain Glow

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

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

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

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

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

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

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

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Home spotlights in Canaan

CROP AND
SADDLE

A LITTLE
LOVE NOTE

THE GOLDEN
DAWN

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

Most popular homes in Canaan.

Sunset
Heart

The Mountain
Glow

Long
Point

Coastal
Rhapsody

The Berkshires
Splendour

Sea
Aster

The
Edge

Reynard's
Den

Sunset
Heart

The Mountain
Glow

Long
Point

Coastal
Rhapsody

The Berkshires
Splendour

Sea
Aster

The
Edge

Reynard's
Den

Dahlia
Darling

Check rates and availability for Canaan.

Book with Plum Guide.

Frequently Asked Questions

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

Home spotlights in Canaan

CROP ANDSADDLE

A LITTLELOVE NOTE

THE GOLDENDAWN

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

Most popular homes in Canaan.

SunsetHeart

The MountainGlow

LongPoint

CoastalRhapsody

The BerkshiresSplendour

SeaAster

TheEdge

Reynard'sDen

SunsetHeart

The MountainGlow

LongPoint

CoastalRhapsody

The BerkshiresSplendour

SeaAster

TheEdge

Reynard'sDen

DahliaDarling

Check rates and availability for Canaan.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Canaan?

CROP AND
SADDLE

A LITTLE
LOVE NOTE

THE GOLDEN
DAWN

Sunset
Heart

The Mountain
Glow

Long
Point

Coastal
Rhapsody

The Berkshires
Splendour

Sea
Aster

The
Edge

Reynard's
Den

Sunset
Heart

The Mountain
Glow

Long
Point

Coastal
Rhapsody

The Berkshires
Splendour

Sea
Aster

The
Edge

Reynard's
Den

Dahlia
Darling