Oak Hill

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

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

Board Games

Amazon Prime

Netflix

Entertainment

Bathtub

Hair Dryer

Toiletries

Bathroom

Dishwasher

Microwave

Freezer

Espresso Machine

Pod Coffee Machine

Fridge

Oven

Stove

Toaster

Kitchen

Coffee Maker

Kitchen Utensils

Cooking Essentials

Kettle

Blender

Kitchen & Dining

Washing Machine

Dryer

Iron

Ironing Board

Black-Out Blinds

Hangers

Extra Pillows and Blankets

Bedroom & Laundry

Hot Tub

Wellness & Fitness

Wi-fi

Laptop Friendly Workspace

Internet & Office

Fireplace

Air Conditioning

Central Heating

Ceiling Fans

Heating & Cooling

Parking Available

Free Parking On Premises

Self Check-in / Check-out

Private Entrance

Single-Level Home

EV Charger

Parking & Access

Balcony

Garden

Barbeque

Outdoor Seating

Outdoor Fireplace / Firepit

Outdoor

Smoke Detector

Carbon Monoxide Detector

First Aid Kit

Fire Extinguisher

Other

Explore ten acres of lush, green land at this cosy ranch, which lies just eight miles from the historic town of Windham. From its perch high up on a hill, you’ll have incredible views of the rolling fields down below. Watch the sun set over the Catskills mountains from the fire pit, or enjoy an al fresco meal on the deck, admiring the beautiful autumnal colours of the trees if you visit in fall. Inside, enjoy meals around the sociable dining room table, which boasts views of the countryside. On cooler evenings, sink into the sofas in the comfortable living room and warm up in front of the wood-burning fireplace.

Autumnal Colours

Sound System

Library of Books

Cleaning Products

Sauna

Free Parking On Street

Balcony / Patio

Hammock

Patio / Terrace

Pets Allowed

Pets

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

High Chair

Swimming Pool

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

Satellite / Cable TV

Smart TV

Games Room

Home Cinema Setup

Playground

Pool / Snooker Table

Streaming Services

Rain Shower

Bread Maker

Wine Cooler

Luxury Bedding

Exercise Equipment

Jacuzzi

Desk

Workplace

Accessible Parking

Throws

Welcome Hamper

Nice to haves

Safe

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

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

Sonos

Bathrobes

Heated Towel Rail

Luxury Toiletries

Ice Machine

Juicer

Mini Bar

Trash Compactor

Wine Cellar

Cot / Crib

Drying Rack

Laundry Supplies

Vacuum Cleaner

Access to Gym / Spa

Sauna / Steam Room

Tennis Court

Temperature Control

Underfloor Heating

Access to Beach

Beach / Pool Towels

Beach Essentials

Fenced Garden

Fenced Pool

Fenced Property

Rooftop Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

Child Friendly

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

XBox

Games Console

Baby Bath

Cafetiere

Children's Dinnerware

Rice Maker

Desk / Workplace

Electricity Adaptors

Printer

Bike Shed

Early / Late Check-Out Available

Helipad

Garden Games

Umbrellas

Alarm System

Security Cameras

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

Piano

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

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

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

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

Stair Gates

This 150-year-old Hudson Valley farmhouse sits on 16 acres of land that includes an apple orchard. It’s an idyllic base for those seeking an escape to the peace of the Catskills – though the town of Windham is just a ten-minute drive. If you tire of hiking, biking and fishing, you can always indulge in a spot of antiquing. The home is owned by a former interiors editor, which explains why it looks like it’s come straight from the pages of a magazine – the rustic style is oh-so charming. The loft bedroom is best suited to older children who won’t mind the ladder or lack of privacy. 

The Architect's Gallery

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

Private Washing Machine

Private Dryer

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

Burnt Sienna

DVD Player

DVD Library

Projector

Private Pool

Step-Free Access

Herb Garden

Outdoor Audio

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

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

Bicycles

Pet Bowls

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

In the town of Ossining on the banks of the Hudson River, this home is reminiscent of an English Tudor mansion on the outside. Inside, there’s plenty of social space for the group to spread out – playing a game of pool in the main living room, settling in to watch Netflix by the fire, in the dedicated media room upstairs or perhaps sipping an old fashioned at the wet bar in the “sky lounge” at the top of the house. Those that need to work remotely can take advantage of the lightning-fast Wifi and two dedicated offices for private calls. While the chef of the group will love the custom, gourmet kitchen in shining marble and granite. Outside, there’s even more space to enjoy with a crystal-clear swimming pool (with a basketball hoop) at the centre of the backyard and numerous seating areas scattered around the terrace. Mountain views from the top floor are a reminder that the hiking trails of Hook Mountain and Rockefeller State Park are both a short drive away. You’re also close to Ossining station, where you can take the Hudson line and be in the centre of NYC in an hour.  

Tudoresque

Ping Pong Table

Indoor Pool

Just a two-hour drive from New York City, this home in the Poconos is more like a private resort, with an impressive list of amenities and all kinds of entertainment options for a large group. Set less than ten minutes away from scenic Lake Harmony by car, and close to various ski resorts like Jack Frost and Big Boulder Mountain, there are shops and restaurants within a few minutes drive, along with nearby golf courses and a water park.

But that's assuming you'll even want to leave this magnificent home. With four bedrooms, a vast games room, indoor and outdoor pools, a cinema room and a bar, you'll have everything you could need right here. Spend your days lounging by the pool, relaxing in the sauna or indoor hot tub, or playing volleyball in the grounds, while evenings mean film screenings, group barbecues and games of air hockey and pool. And before bed, there's just time for nightcaps around the fire pit.

 

 

The Masterplan

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

Record Player

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

Book a stay in one of the best homes in Oak Hill

We selected the 934 homes worth renting in this location

Who's coming along?

Home spotlights in Oak Hill

We selected the top 3% holiday homes in Oak Hill

Most popular homes in Oak Hill

Check upcoming rates & availability for Oak Hill

Frequently asked questions