Olivebridge

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

Amazon Prime

Netflix

Satellite / Cable TV

Board Games

Library of Books

Streaming Services

Entertainment

Bathtub

Hair Dryer

Rain Shower

Toiletries

Bathroom

Blender

Children's Dinnerware

Coffee Maker

Cooking Essentials

Dishwasher

Espresso Machine

Freezer

Fridge

Kettle

Kitchen

Kitchen Utensils

Microwave

Oven

Pod Coffee Machine

Rice Maker

Stove

Toaster

Kitchen & Dining

Private Washing Machine

Private Dryer

Black-Out Blinds

Cleaning Products

Cot / Crib

Dryer

Drying Rack

Extra Pillows and Blankets

Hangers

Iron

Ironing Board

Laundry Supplies

Vacuum Cleaner

Washing Machine

Bedroom & Laundry

Desk

Electricity Adaptors

Laptop Friendly Workspace

Printer

Wi-fi

Internet & Office

Air Conditioning

Ceiling Fans

Central Heating

Fireplace

Temperature Control

Heating & Cooling

Free Parking On Street

Free Parking On Premises

Multiple Sets of Keys

Parking Available

Private Entrance

Self Check-in / Check-out

Parking & Access

Balcony

Barbeque

Garden

Hammock

Outdoor Fireplace / Firepit

Outdoor Seating

Patio / Terrace

Sun Umbrellas

Outdoor

Throws

Umbrellas

Nice to haves

Pets Allowed

Pets

Carbon Monoxide Detector

Fire Extinguisher

First Aid Kit

Safe

Security Cameras

Smoke Detector

Other

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 the patio is ideal come summertime. Other features to admire are the unique ornaments collected by the lovely host, Minetta.

Burnt Sienna

Sound System

Sun Loungers / Beach Chairs

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

Baby Bath

Changing Table

High Chair

Baby Monitor

Hot Tub

Jacuzzi

Exercise Equipment

Wellness & Fitness

Accessible Parking

EV Charger

Balcony / Patio

Welcome Hamper

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

DVD Library

Smart TV

Record Player

Mini Bar

Swimming Pool

Bicycles

Heated Pool

Buzzer / Wireless Intercom

Single-Level Home

Beach Essentials

Urbanites looking for a tranquil getaway will enjoy the large indoor and outdoor spaces to relax and unwind. Each room has been lovingly styled by the host, Ayanna, who has instilled her character and charm into the home. The location has a semi-rural feel, which is wonderfully peaceful, but The Archway is still located near to the village centre. The home is well suited for families as there's lots of room for children to play and the twin bedroom has been thoughtfully designed to welcome young ones. 

The Archway

Piano

Bathrobes

Cafetiere

Desk / Workplace

Workplace

Underfloor Heating

Beach / Pool Towels

Outdoor Audio

Access to Beach

Outdoor Kitchen

Mosquito Net

Stair Gates

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home. It was proudly featured in Italy's Icon Design Magazine for its attention to detail and considered use of elegant and characterful materials. 

We loved the living space, particularly the expansive ceilings, enormous windows and integration of concrete and wood. Rise and shine to picturesque views of the beautiful garden. Relax on the outdoor day bed, which looks out over the legendary Indian Head mountain ridge, have a picnic by the swimming pond, surrounded by juniper trees and century-old cedars, or follow the burbling stream into the woods. Then later, gather around the fire pit. Whatever you decide to do, this home invites you to slow down the pace in style.

If you'd like to explore further afield, lace-up your boots and take a drive out to a hiking trail  –  the Indian Head Wilderness and the Bluestone Wild Forest are no more than fifteen minutes away. 



The Pond House

Luxury Toiletries

Child Friendly

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 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

Tucked neatly at the border of the Catskills, this chalet in Lake Hill is an idyllic home for those seeking an alpine retreat. With Cooper Lake and the Mink Hollow hiking trail nearby, it’s effortless to reconnect with nature here. Back at home, this modern cabin considers your every need after a day out in Woodstock, just four miles away. There’s a hammock, sound system, record player and fire pit for cosy nights at home. And while the lofted bedrooms aren’t so private, there’s plenty of space for a couple of friends to spend quality time.

Hearthside Haven

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

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

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

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

Games Room

Home Cinema Setup

Playground

Pool / Snooker Table

Bread Maker

Wine Cooler

Luxury Bedding

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

Sonos

Heated Towel Rail

Ice Machine

Juicer

Trash Compactor

Wine Cellar

Access to Gym / Spa

Sauna

Sauna / Steam Room

Tennis Court

Fenced Garden

Fenced Pool

Fenced Property

Rooftop Terrace

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

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

XBox

Games Console

Bike Shed

Early / Late Check-Out Available

Helipad

Garden Games

Alarm System

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

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

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

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

DVD Player

Projector

Private Pool

Step-Free Access

Herb Garden

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

Book a stay in one of the best homes in Olivebridge

We selected the 936 homes worth renting in this location

Who's coming along?

Home spotlights in Olivebridge

We selected the top 3% holiday homes in Olivebridge

Most popular homes in Olivebridge

Check upcoming rates & availability for Olivebridge

Frequently asked questions