Chester

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

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

Sound System

Library of Books

Board Games

Ping Pong Table

Entertainment

Bathtub

Hair Dryer

Toiletries

Bathroom

Pod Coffee Machine

Microwave

Fridge

Oven

Stove

Toaster

Freezer

Kitchen

Coffee Maker

Kitchen Utensils

Cooking Essentials

Kettle

Blender

Dishwasher

Kitchen & Dining

Washing Machine

Dryer

Iron

Hangers

Extra Pillows and Blankets

Cleaning Products

Bedroom & Laundry

Exercise Equipment

Wellness & Fitness

Wi-fi

Laptop Friendly Workspace

Internet & Office

Fireplace

Central Heating

Ceiling Fans

Heating & Cooling

Parking Available

Free Parking On Premises

Free Parking On Street

Private Entrance

Single-Level Home

Self Check-in / Check-out

Parking & Access

Barbeque

Balcony / Patio

Garden

Beach Essentials

Hammock

Outdoor Seating

Outdoor Shower

Outdoor Fireplace / Firepit

Outdoor

Throws

Umbrellas

Nice to haves

Pets Allowed

Pets

Child Friendly

Smoke Detector

Carbon Monoxide Detector

First Aid Kit

Fire Extinguisher

Other

It's back to camp at this lakeside home, which has been designed to make the most of its beautiful surroundings. Wooden floorboards, adjoining cabins, folding doors, and outdoor walkways give the sense of being in a giant – and rather quirky – treehouse. First up on your camp agenda will be running wild in the gorgeous grounds. We love the array of activities the spot has on offer, with a barbecue, fire pit, ping pong and foosball tables, kayaks, and a deck to jump straight into the freshwater lake. When you're not exploring the surrounding state parks, the home is full of nooks and crannies to explore. Lounge in the Japanese soaking tub, lie back in an indoor hammock, or watch the sunset from the deck before planning another day of action at this peaceful hideaway.


Pine's Reach

Desk / Workplace

Air Conditioning

Balcony

Welcome Hamper

Safe

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

Amazon Prime

Netflix

Satellite / Cable TV

Smart TV

Games Room

Home Cinema Setup

Playground

Pool / Snooker Table

Streaming Services

Rain Shower

Bread Maker

Wine Cooler

Ironing Board

Luxury Bedding

Hot Tub

Jacuzzi

Swimming Pool

Desk

Workplace

Accessible Parking

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

Children's Dinnerware

Espresso Machine

Rice Maker

Private Washing Machine

Private Dryer

Black-Out Blinds

Cot / Crib

Drying Rack

Laundry Supplies

Vacuum Cleaner

Electricity Adaptors

Printer

Temperature Control

Multiple Sets of Keys

Patio / Terrace

Sun Umbrellas

Security Cameras

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

Sauna

EV Charger

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

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

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

DVD Player

Sonos

DVD Library

Projector

Cafetiere

Mini Bar

High Chair

Private Pool

Step-Free Access

Herb Garden

Outdoor Audio

Sun Loungers / Beach Chairs

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

Baby Monitor

Bicycles

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

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

Luxury Toiletries

Just steps away from a private community beach, Borne Back was designed by its architect owner to provide a comfortable contemporary home in a perfectly quiet spot in the Hamptons. On a full acre plot next to Gardiner's Bay, it's surrounded by tall trees. Inside, it's modern, bright and relaxing, with subtle nods to its coastal location. Cook in the state-of-the-art kitchen, barbecue outside on the terrace or screen a movie on the home cinema setup. There's ample outdoor seating and a delightful, heated private pool to enjoy, and in the evenings, you could always treat your loved ones to a performance on the home's drumkit. We love the huge, sociable sofa in the living room and the first-floor sun terrace in particular but nothing beats the location of this place. A matter of metres from the beach and surrounded by quiet streets perfect for walks and bike rides, it's also within easy reach of several shops and restaurants.

Borne Back

Heated Pool

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

Trash Compactor

Access to Beach

Beach / Pool Towels

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

Baby Bath

Changing Table

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

Bathrobes

Heated Towel Rail

Ice Machine

Juicer

Wine Cellar

Access to Gym / Spa

Sauna / Steam Room

Tennis Court

Underfloor Heating

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

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

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

Mere steps from the beach, this four-bedroom farmhouse sleeps ten and is ideal for a large family getaway. Rustic it may be, but the interiors don’t skimp on style – white walls and pops of colour lend it a modern Scandinavian vibe. An open-plan kitchen with a Carrara marble island and KitchenAid mixer make meal prep a cinch – get everyone together to bake a cake. A travel crib, highchair and changing pad are provided for the littlest family members. 

The Captain's House

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

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

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

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

Book a stay in one of the best homes in Chester

We selected the 954 homes worth renting in this location

Who's coming along?

Home spotlights in Chester

We selected the top 3% holiday homes in Chester

Most popular homes in Chester

Check upcoming rates & availability for Chester

Frequently asked questions