Olivebridge

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What at first glance appears to be an abandoned wooden turret lives a secret life as a blissful modern retreat, in this converted willow silo. Nestled amongst the trees ten minutes away from Woodstock, this wondrous three-storey tower is as well positioned to hiking nearby woods and mountains as it is to the galleries and boutiques of Woodstock. Keen skiers will love staying here thanks to its close proximity to the Hunter ski centre, a 30-minute drive away. Discover the hidden lakes and waterfalls nearby by day, and stargaze from your own hammock by night. By the time you leave, you'll be at one with the woods. 

Soul Of The Willow

The Ashokan is an exquisite barn-styled house nestled within rich woodland landscape. The quaint exterior shelters an incredibly contemporary and stylish interior. From the patterned floors and wonderful impressionist paintings, to the rustic oak furnishings and floorboards, this house seamlessly blends homeliness with elegance. The large bedrooms have plush deluxe beds (although the mezzanine bedroom offers very little privacy and has no curtains), as well as plentiful dressing space and luxurious bathrooms. The estate is located moments away from the beautiful Ashokan reservoir. Spend your days taking in the breathtaking landscape while hiking the trails, or perhaps head into the nearby Woodstock to wander around the legendary town. 

The Ashokan

This country home is located on 6 acres of private land, so there’s plenty of outdoor space to enjoy here. We love the scenic views from the terrace, where you’ll have a front row seat to watch the sun set behind the surrounding hills and a fire pit to keep you warm on chilly evenings. Inside boasts an open-plan living/dining area with a fireplace – perfect for cosy nights in – and a huge home office, which can double up as a second lounge if you don’t need to work while you’re away. When it comes to exploring the area, you’ll find walking trails nearby – including one that takes you to picturesque Lake Quassapaug  – and a trio of beaches within driving distance.

The Rainbow Bird

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

Anyone with a subscription to HBO might recognise The Old Life-Saving Station. The home has featured in both Lena Dunham’s Girls, and more recently, The Undoing, starring Hugh Grant and Nicole Kidman. Staying here puts you in elite company, and it’s not hard to see why. It’s a unique house. Dating all the way back to the 1800s, when it was built as a coastguard station for the Long Island Sound, it’s been renovated since, but with lots of care put into maintaining the farmhouse atmosphere and the vintage furniture. The home is set on three acres of land on the North Fork, and from the veranda, you can hear the waves lapping against the shore of the private beach. It’s a magical setting, perfect for long summer afternoons (and if the water is too cold, there’s a 50ft pool as well). Colder evenings bring their own charm, as the vast kitchen and living room come into play. The large table seats fourteen easily, so every night feels like a dinner party, while the crackling fire in the other room sets the scene for an evening curled up on the sofa, with a hot drink in hand.

The Old Life-Saving Station

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

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

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

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

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

A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light. It's the ideal family pad, especially with a lounge fit for kids (complete with a pool table) in the basement and a workout room (including a Peloton bike) that fitness buffs will appreciate. And there's no denying that there's plenty of space to spread out. Two main suites have parents and in-laws covered, the sunroom is an excellent spot to enjoy a cup of tea in the afternoons and the kitchen is a dream to cook in, with glossy tiles, high-end appliances and all the crockery you'll need.

Make your way outside and while away sunny days by the pool. Come evening, fire up the barbecue and tuck into an alfresco feast before gathering around the fire pit on the Adirondack chairs to watch the stars come out. The peaceful scenery is made even better by the excellent location. This home is tucked away on a tree-lined cul-de-sac that backs up to a nature preserve, with walking trails right on your doorstep. It's an easy seven-minute drive to the stores, restaurants and coffee shops in East Hampton, while Two Mile Hollow Beach and other stretches of sandy coastline are just eleven minutes away.

Summer Fridays

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.

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Types

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

We selected the 926 homes worth renting in this location

Who's coming along?

Home spotlights in Olivebridge

SOUL OF
THE WILLOW

THE
ASHOKAN

THE RAINBOW
BIRD

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

Most popular homes in Olivebridge.

Coastal
Rhapsody

The Old
Life-Saving Station

Reynard's
Den

The Creekside
Cabin

Cottontail
Creek

River
Song

Sunflower
Summer

Summer
Fridays

Coastal
Rhapsody

The Old
Life-Saving Station

Reynard's
Den

The Creekside
Cabin

Cottontail
Creek

River
Song

Sunflower
Summer

Summer
Fridays

Building
Bridges

Check rates and availability for Olivebridge.

Book with Plum Guide.

Frequently Asked Questions

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

We selected the 926 homes worth renting in this location

Home spotlights in Olivebridge

SOUL OFTHE WILLOW

THEASHOKAN

THE RAINBOWBIRD

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

Most popular homes in Olivebridge.

CoastalRhapsody

The OldLife-Saving Station

Reynard'sDen

The CreeksideCabin

CottontailCreek

RiverSong

SunflowerSummer

SummerFridays

CoastalRhapsody

The OldLife-Saving Station

Reynard'sDen

The CreeksideCabin

CottontailCreek

RiverSong

SunflowerSummer

SummerFridays

BuildingBridges

Check rates and availability for Olivebridge.

Book with Plum Guide.

Frequently Asked Questions

Can I see the best in Olivebridge?

SOUL OF
THE WILLOW

THE
ASHOKAN

THE RAINBOW
BIRD

Coastal
Rhapsody

The Old
Life-Saving Station

Reynard's
Den

The Creekside
Cabin

Cottontail
Creek

River
Song

Sunflower
Summer

Summer
Fridays

Coastal
Rhapsody

The Old
Life-Saving Station

Reynard's
Den

The Creekside
Cabin

Cottontail
Creek

River
Song

Sunflower
Summer

Summer
Fridays

Building
Bridges