Chatham

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

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

Library of Books

Entertainment

Hair Dryer

Toiletries

Bathroom

Freezer

Pod Coffee Machine

Fridge

Oven

Stove

Kitchen

Coffee Maker

Kitchen Utensils

Cooking Essentials

Kitchen & Dining

Washing Machine

Dryer

Iron

Cot / Crib

Hangers

Bedroom & Laundry

Wi-fi

Laptop Friendly Workspace

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Multiple Sets of Keys

Parking Available

Free Parking On Premises

Self Check-in / Check-out

Private Entrance

Parking & Access

Balcony / Patio

Garden

Outdoor

Throws

Breakfast Included

Nice to haves

Pets Allowed

Pets

Child Friendly

Smoke Detector

Carbon Monoxide Detector

First Aid Kit

Fire Extinguisher

Other

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

Home Cinema Setup

DVD Player

Netflix

Amazon Prime

Sonos

Board Games

DVD Library

Projector

Satellite / Cable TV

Sound System

Bathtub

Dishwasher

Microwave

Cafetiere

Mini Bar

Wine Cooler

High Chair

Ironing Board

Extra Pillows and Blankets

Swimming Pool

Hot Tub

Private Pool

Wellness & Fitness

Electricity Adaptors

Fireplace

Step-Free Access

Herb Garden

Barbeque

Outdoor Audio

Patio / Terrace

Balcony

Sun Loungers / Beach Chairs

Umbrellas

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

Free Parking On Street

Outdoor Fireplace / Firepit

Outdoor Seating

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

Espresso Machine

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

Streaming Services

Rain Shower

Blender

Children's Dinnerware

Kettle

Rice Maker

Toaster

Private Washing Machine

Private Dryer

Black-Out Blinds

Cleaning Products

Drying Rack

Laundry Supplies

Vacuum Cleaner

Desk

Printer

Ceiling Fans

Temperature Control

Hammock

Sun Umbrellas

Safe

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

Burnt Sienna

Desk / Workplace

Welcome Hamper

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

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

Pool / Snooker Table

Bathrobes

Heated Towel Rail

Luxury Toiletries

Ice Machine

Juicer

Trash Compactor

Wine Cellar

Luxury Bedding

Access to Gym / Spa

Exercise Equipment

Jacuzzi

Sauna

Sauna / Steam Room

Tennis Court

Workplace

Underfloor Heating

Access to Beach

Beach / Pool Towels

Beach Essentials

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

XBox

Games Console

Baby Bath

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

Bicycles

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

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

Smart TV

Games Room

Playground

Bread Maker

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

Private Parking

Single-Level Home

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

This home's architecture, interiors and colourful prints all share a mid-century modern style, but its woodland surroundings are more Hansel and Gretel than Gilbert and George. In a tiny hamlet in upstate New York, it’s surrounded by mountains, lakes and forest – great for skiers, hikers and wild swimmers alike. The home has several standout features but we love the double-height living area, with its huge windows and cosy fireplace. The galleried landing has a desk in case you need to keep one eye on work while you're away, and the huge deck has a gas barbecue for those long lazy lunches outdoors. While its statement design pieces add interest, it's a homely place too, with a bedroom set up for children, logs provided for the fire, and plenty of books to pick through on the shelves. Just minutes from a choice of state parks, forests, orchards, and wineries, your days will be filled with outdoor adventures – and all just an easy drive from the city.


Art & Nature

Ping Pong Table

Indoor Pool

EV Charger

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

Record Player

Free Parking

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

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

Baby Monitor

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

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

Mosquito Net

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

Book a stay in one of the best homes in Chatham

We selected the 918 homes worth renting in this location

Who's coming along?

Home spotlights in Chatham

We selected the top 3% holiday homes in Chatham

Most popular homes in Chatham

Check upcoming rates & availability for Chatham

Frequently asked questions