Berkshire County

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Library of Books

Sonos

Board Games

Satellite / Cable TV

Sound System

Piano

Entertainment

Bathtub

Hair Dryer

Toiletries

Bathroom

Dishwasher

Microwave

Freezer

Pod Coffee Machine

Fridge

Oven

Stove

Toaster

Kitchen

Coffee Maker

Kitchen Utensils

Cooking Essentials

Kettle

Blender

Kitchen & Dining

Washing Machine

Dryer

Iron

Ironing Board

Hangers

Extra Pillows and Blankets

Cleaning Products

Black-Out Blinds

Bedroom & Laundry

Wi-fi

Desk / Workplace

Laptop Friendly Workspace

Internet & Office

Fireplace

Air Conditioning

Central Heating

Heating & Cooling

Parking Available

Free Parking On Premises

Private Entrance

Free Parking On Street

Self Check-in / Check-out

Parking & Access

Barbeque

Balcony

Garden

Outdoor Fireplace / Firepit

Outdoor Seating

Sun Loungers / Beach Chairs

Outdoor

Throws

Welcome Hamper

Nice to haves

Pets Allowed

Pets

Smoke Detector

Carbon Monoxide Detector

First Aid Kit

Fire Extinguisher

Other

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice. This place is made for taking it back to analogue and spending quality time together, around the stand-up piano, playing a board game in the sunny second sitting room, or pausing for a moment in the secret reading nook. A low, wooden ceiling, exposed brick wall and a wood-burning stove in the main lounge provide the ‘cosy’, while the plush velvet armchairs and antique dining table provide the ‘divine’. The bistro seating in the kitchen comes with a view of Butternut Mountain. Plus, there are several laptop-friendly desks designed for remote working and a dedicated office for video calls.

Outside, (well, almost outside) you’ve got an enclosed front porch with deck chairs for sunny days and a first-floor balcony begging for an evening tipple. In the surrounding greenery of the garden, let the kids run free on the lawn before gathering the group around the fire pit for a spot of stargazing at night.

You’re a five-minute drive from the artisan shops, local markets and restaurants of Great Barrington here, and skiing on Butternut Mountain is a short drive away too. 

Divine Inspiration

Amazon Prime

Netflix

Streaming Services

Children's Dinnerware

High Chair

Cot / Crib

Bicycles

Wellness & Fitness

Private Parking

Single-Level Home

Patio / Terrace

Beach Essentials

Child Friendly

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

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

Smart TV

Home Cinema Setup

Record Player

Luxury Toiletries

Ice Machine

Juicer

Mini Bar

Rice Maker

Trash Compactor

Private Washing Machine

Private Dryer

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Desk

Ceiling Fans

Temperature Control

Accessible Parking

Free Parking

Early / Late Check-Out Available

Herb Garden

Outdoor Audio

Outdoor Kitchen

Safety Gates

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

Foosball / Table Football

Games Room

Ping Pong Table

Pool / Snooker Table

Bathrobes

Wine Cooler

Exercise Equipment

Hot Tub

Steam Room

Printer

Underfloor Heating

Ski Storage / Boot Room

Beach / Pool Towels

Alarm System

Safe

Security Cameras

Security System

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

Balcony / Patio

Built in 1800, Hitchbrook is a quintessential New England home. Surrounded by farmland and rolling hills, this home is a private getaway for those looking for a pastoral retreat. Think rustic but sophisticated; evenings in front of fireplace or relaxing in the den playing games and singing-along to the piano. There are some great hikes nearby – the hills of Hitchcock Corners and across from Mill Brook are wonderful for walking. For the cyclists, there are plenty of bike trails to get stuck into. We’d recommend picking up some supplies from the neighbouring villages of Millbrook and Lakeville, and crossing the border into upstate New York for a picnic. 

Hitchbrook

Playground

Rain Shower

Bread Maker

Jacuzzi

Swimming Pool

Workplace

If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home. Outside, guests have access to a private pool, basketball hoop, and terrace, ideal for drinks at sundown. In terms of location, you’re an hour’s drive from New York City. Should you need help with planning your itinerary, your host provides a handy digital guide. 

A Summer's Eve

Heated Towel Rail

Espresso Machine

Wine Cellar

Drying Rack

Access to Gym / Spa

Sauna

Sauna / Steam Room

Tennis Court

Access to Beach

Fenced Garden

Fenced Pool

Fenced Property

Rooftop Terrace

Sun Umbrellas

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

EV Charger

Hammock

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

Paid Parking On Premises

This calming home-from-home is close enough to nip into the city on the subway, yet sits in a quiet and friendly neighbourhood in Astoria, Queens. Surrounded by leafy green parks, independent coffee shops, and a host of world cuisine eateries, it's the perfect spot for those looking to see the sights of NYC with a comforting place to call home outside of the concrete jungle. Inside, from the moment you enter the home, there's a real sense of space, with an open concept floor plan and clever design. Natural light floods into the living room through the windows and neutral tones of grey, white and moody blue create a soothing space to relax in after a day wandering the city. The sleek white kitchen comes with an equally elegant dining room that's perfect for big American breakfasts while the dedicated work desk accommodates those in town on business. Whether you're strolling through the local green spots, living it up in the city, or in-and-out with work, this charming apartment is a rare pocket of calm withdrawn from the hustle and bustle.

Building Bridges

Baby Bath

Changing Table

Baby Monitor

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

XBox

Games Console

Cafetiere

Electricity Adaptors

Bike Shed

Helipad

Garden Games

Umbrellas

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

Multiple Sets of Keys

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 other features to admire are the unique ornaments collected by the lovely host, Minetta.

Burnt Sienna

Sitting peacefully on the edge of North Twin Lakes, this stylish cottage sets the tone for a restorative retreat in Livingston. Featuring beautiful views, calm rooms and a range of personal touches, you’ll find everything you could need to disconnect and embrace the natural elements. Complimentary toiletries are provided and children’s amenities are available on request, plus there are plenty of entertainment options – including board games, Bluetooth Speakers, Smart TVs and three kayaks. Outside, you’ll find a private beach, a fire pit and easy access to the nearest amenities. 

Lake of Beauty

Heated Pool

Outdoor Shower

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

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

Breakfast Included

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

DVD Player

DVD Library

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

This delightful cottage, nestled in the picturesque mountains of New York State’s famous Shawangunk Ridge, is an ideal spot for a cosy country escape. As the last property before the entrance to a protected nature reserve, this home offers unmatched tranquillity and proximity to nature.

The homely interior draws inspiration from the ancient woodlands and gorgeous landscape outside. Wooden floorboards pair with bright houseplants to create an organic and breathable ambience throughout, and there is a charming fireplace set within a stone wall for added cosiness.  The exquisite evergreen kitchen has stylish bar stools that invite you to enjoy quiet, home-cooked dinners, while the plush, deluxe king-sized bed in the bedroom carries the promise of a restful night’s sleep.

The cottage's location offers the best of both worlds – you’ll be able to breathe in the fresh outdoor air on nearby Minnewaska State Park Preserve and wander through its magical trails, safe in the knowledge that all the comforts of modern living are within a fifteen-minute drive away. This is also the best place for rock-climbing and mountain biking – if you like to live dangerously! 


Under The Ridge

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