Chatham holiday rentals

We found 1,288 holiday rentals — enter your dates for availability
Discover a selection of 12 homes and other holiday rentals in Chatham that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a garden. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Chatham

Showing deals for:11 Dec - 18 Dec

Dining
The great room with wonderful water views and working fireplace
Open kitchen to great room, wonderful for cooking and entertaining
Hot tub overlooking the lake
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
AU$6,421
for 7 nights, 1 home
AU$917 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
View from the lawn by the water
view from the 2nd bedroom
View of the lower deck from the sunroom
Open plan dining area with water views and access to the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$6,783
for 7 nights, 1 home
AU$969 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Interior
Exterior detail
Kitchen
Interior
Exceptional
(71 reviews)

Beautiful Modern Swiss Cottage in Athens, NY

Athens

12% off
AU$3,873
for 7 nights, 1 home
AU$553 per night
includes taxes & fees
Beautiful Modern Swiss Cottage in Athens, NY
Dining
Living area
Master suite balcony
Front porch
Exceptional
(34 reviews)

Luxury secluded Catskill log cabin on creek-ski hike great restaurants mins away

Catskill

8% off
AU$4,395
for 7 nights, 1 cabin
AU$628 per night
includes taxes & fees
Luxury secluded Catskill log cabin on creek-ski hike great restaurants mins away
Interior
Terrace/patio
Exterior
Dining
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington

8% off
AU$3,395
for 7 nights, 1 cottage
AU$485 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Property grounds
3 decks, a fire pit overlooking the lake, rock beach and private dock
Living area
Property grounds
Exceptional
(147 reviews)

Waterfront Luxe: Kayak & SUP From Private Dock, Pong & Air Hockey, Near Hudson

Coxsackie

8% off
AU$6,048
for 7 nights, 1 home
AU$864 per night
includes taxes & fees
Waterfront Luxe: Kayak & SUP From Private Dock, Pong & Air Hockey, Near Hudson
3 season Sunroom
Property grounds
House 1- Mountain views from this open concept kitchen, dining, sitting room
Welcome!
Exceptional
(6 reviews)

Grand Estate w/ Mountain Views by Evergreen Home

Ghent

11% off
AU$8,567
for 7 nights, 1 home
AU$1,224 per night
includes taxes & fees
Grand Estate w/ Mountain Views by Evergreen Home
Exterior
Private kitchen
Living area
Property grounds
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$5,173
for 7 nights, 1 home
AU$739 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Enclosed porch- view into back yard- dining/game table
Kitchen with counter seating for 4- door on the right to garage
Property grounds
Outdoor dining
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
AU$5,253
for 7 nights, 1 home
AU$750 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Looking towards outside deck and tiv area in fireplace sitting area
Front showing deck on the side of the house in both levels
Kitchen island with 2 swivel chairs and pantry, and coat closet with barn doors
Interior
Exceptional
(133 reviews)

Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

8% off
AU$3,369
for 7 nights, 1 home
AU$481 per night
includes taxes & fees
Gorgeous Mountain Views Retreat: Family & Nature
Living room
Kitchen
Dining room
Living room
Exceptional
(5 reviews)

Spacious Lake Community House near Hudson

Coxsackie

9% off
AU$3,626
for 7 nights, 1 home
AU$518 per night
includes taxes & fees
Spacious Lake Community House near Hudson
Dining Room w/ Doors to Screened Porch Dining Area
Fully screened porch!
Front Staircase
Reading nook with natural lighting
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
AU$4,210
for 7 nights, 1 home
AU$601 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Dining
Interior
Property grounds
Exterior
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,743
for 7 nights, 1 cabin
AU$535 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Outdoor dining
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$5,835
for 7 nights, 1 home
AU$834 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Games room
Terrace/patio
Private kitchen
Pool
Exceptional
(5 reviews)

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale

7% off
AU$8,178
for 7 nights, 1 home
AU$1,168 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Enjoy the view of kitchen activities while hanging out on the couch.
View of the cabin from the road. Sitting on just over an acre of land.
A clean, simple hallway that leads to the downstairs bedroom and bathroom.
Entertainment meets comfort here. Enjoy a movie night on the big screen.
Exceptional
(41 reviews)

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Catskill

8% off
AU$2,350
for 7 nights, 1 cabin
AU$336 per night
includes taxes & fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
The living room flows into the dining room.
You will love dining and working in this rich and colorful room
A mudroom off the back leads to the large wooden deck
Outdoor dining and grill on the 16' x 20' wooden deck.
Exceptional
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$4,835
for 7 nights, 1 home
AU$691 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Double height, open kitchen and dining perfect for large vacation meals
Patio accessible from dining/kitchen
Walnut dining table seats ten
Front Door entrance
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

8% off
AU$5,443
for 7 nights, 1 home
AU$778 per night
includes taxes & fees
Designer Home with Panoramic Views near Hudson
Room
Interior
Interior
Living area
Exceptional
(41 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
AU$2,382
for 7 nights, 1 home
AU$340 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Living area
Outdoor dining
Exterior
Room
Exceptional
(10 reviews)

Glass Lake Cottage

Averill Park

8% off
AU$4,542
for 7 nights, 1 home
AU$649 per night
includes taxes & fees
Glass Lake Cottage
Exterior
Private kitchen
view of cottage from the road and parking to the right
Living area
Exceptional
(109 reviews)

1930's 1 bedroom cottage updated with charm, pet friendly, near hiking trails

Catskill

8% off
AU$1,110
for 7 nights, 1 cottage
AU$159 per night
includes taxes & fees
1930's 1 bedroom cottage updated with charm, pet friendly, near hiking trails
Private kitchen
Interior
Pool
Living area
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,362
for 7 nights, 1 home
AU$623 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Open kitchen area with bar seating, great for socializing while you meal prep.
Second story deck with lake views, dining table for 8, sitting area and grill
Open and bright main floor living space with stunning views of Laurel Lake.
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

16% off
AU$5,388
for 7 nights, 1 home
AU$770 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Private kitchen
Ultimate Relaxation! The hot tub will be warm and waiting for your arrival
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Open floor plan, natural light in a stylish space
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$3,983
for 7 nights, 1 home
AU$569 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Friendly Chatham will entice you

Enjoy the theatre scene and other features of Chatham. Travellers appreciate the restaurants in this welcoming city. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Chatham

Are you searching for top things to see and do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Chatham has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Catamount Ski Area (14.9 mi / 24 km)
  • Bousquet Ski Area (16.5 mi / 26.5 km)
  • Wyndhurst Golf & Club (16.8 mi / 27 km)
  • Ski Butternut (18.8 mi / 30.3 km)
  • Lake Taghkanic State Park (19.6 mi / 31.5 km)
  • Hudson Chatham Winery (4.4 mi / 7 km)

Exploring the natural landscape of Chatham

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Chatham is a great place to get out in nature. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Art Omi International Arts Center - Fields Sculpture Park (4.4 mi / 7 km)
  • Kinderhook Lake (7.1 mi / 11.5 km)
  • Queechy Lake (9.7 mi / 15.5 km)
  • Sleepy Hollow Lake (11.8 mi / 19.1 km)
  • Berkshire Botanical Garden (13.9 mi / 22.4 km)
  • Stockbridge Bowl (14.2 mi / 22.9 km)

Transport options to and around Chatham

The nearest airport is in Hudson, NY (HCC-Columbia County), located 7.7 mi (12.4 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away.

Frequently asked questions

What is the best area to stay in Chatham when booking a holiday rental?
When considering a holiday rental in Chatham, New York, the village itself is a delightful area to focus on, particularly for those seeking a charming small-town experience. Chatham boasts a lovely mix of historic architecture and modern amenities, making it a welcoming destination for visitors. The village centre features a variety of properties, ranging from quaint cottages to more spacious homes, providing ample choices for holidaymakers.One of the key attractions in Chatham is the Crandell Theatre, a beautifully restored cinema that showcases independent films and hosts community events, adding a cultural flair to your stay. Additionally, the nearby Chatham Berry Farm is a wonderful spot for families, offering pick-your-own fruit experiences during the summer months and providing a taste of the local agricultural scene.For those who enjoy outdoor activities, the surrounding areas offer access to stunning landscapes, including the scenic views of the nearby Catskill Mountains.
Where are the best areas for renting a beach house in Chatham?
For renting a beach house in Chatham, the area around Chatham Lighthouse Beach is particularly appealing. This picturesque spot offers sandy shores and stunning views of the Atlantic, making it a ideal setting for a seaside getaway. Many holiday rentals in this vicinity come equipped with amenities such as outdoor decks for sunbathing, private gardens for barbecues, and spacious living areas, ideal for families or groups looking to enjoy beachside relaxation.Another excellent choice is the area near Hardings Beach, known for its gentle waves and family-friendly atmosphere. Here, you'll find beach houses that often feature modern kitchens, outdoor showers, and easy access to the beach, enhancing the overall holiday experience. This area also provides close proximity to local shops and eateries, ensuring that guests have all they need within reach.Additionally, the nearby Monomoy National Wildlife Refuge offers opportunities for nature enthusiasts with its scenic trails and birdwatching spots. Rentals in this area typically include amenities like bicycles for exploring the surroundings, making it easy to enjoy both the beach and the beautiful natural landscapes.
Where are the best Chatham ski resort rentals?
For renting near ski resorts in Chatham, New York, enthusiasts should consider the nearby area of Catamount Ski Area, located just a short drive away. In Chatham itself, visitors can find a selection of charming rental properties, including cosy cabins and contemporary homes that often cater to families and groups. Many of these accommodations come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor decks superb for relaxing after a day on the slopes.In addition to Catamount, the surrounding towns like Great Barrington offer additional options with easy access to ski facilities. Here, you might find lodgings that feature amenities like hot tubs, wood-burning stoves, and even game rooms, enhancing the overall experience for those looking to unwind. These rentals frequently provide a warm and inviting atmosphere, ideal for gathering with friends or family.Moreover, the scenic landscapes of the Berkshires provide not only skiing opportunities but also hiking and winter sports, making it a great destination year-round.
What is the most popular type of holiday rental accomodation in Chatham?
In Chatham, holiday houses are the most popular type of holiday rental, with around 36 available throughout the area. These homes typically offer spacious living arrangements, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or gardens, making them ideal for families or groups looking to enjoy the scenic beauty of the Hudson Valley. Additionally, there are about 12 mobile homes, along with several chalets, apartments, and villas, providing a range of options to suit different preferences and budgets.
Are there any family house rentals in Chatham?
In Chatham, New York, there are several family-friendly house rentals available, making it a great choice for those travelling with children. The area is known for its charming rural atmosphere and scenic landscapes, ideal for family adventures. Many of these homes offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can play freely.Visitors can explore nearby attractions such as the picturesque Chatham Village, which features quaint shops and local eateries. Additionally, the surrounding countryside provides ample opportunities for outdoor activities, including hiking and biking along beautiful trails.
Can I rent a holiday home with a pool or hot tub in Chatham?
In Chatham, New York, there are several holiday homes available for rent that feature pools or hot tubs, making it an appealing destination for those looking to relax and unwind. The charming town is known for its picturesque landscapes and proximity to the scenic Berkshires, providing a lovely backdrop for a getaway.Many of the available properties come equipped with amenities such as private pools, hot tubs, and spacious outdoor areas great for enjoying the beautiful surroundings. Inside, travellers can expect fully equipped kitchens, comfortable living spaces, and modern conveniences like Wi-Fi and air conditioning.Chatham's quaint downtown area offers delightful shops and dining options, ensuring that guests have everything they need for a memorable stay.
Are there pet-friendly house rentals in Chatham?
In Chatham, there are several pet-friendly house rentals available for those looking to enjoy a getaway with their furry companions. The charming town offers a variety of properties, often featuring spacious interiors, well-equipped kitchens, and outdoor areas where pets can roam freely. Many rentals come with amenities such as private gardens, patios, and sometimes even fenced yards, ensuring a comfortable stay for both guests and their pets.Additionally, Chatham's scenic surroundings provide ample opportunities for outdoor activities, with nearby parks and nature trails great for walks and exploration. The local community is welcoming to pet owners, with several pet-friendly cafes and shops ideal for travellers with pets.
Are there any remote work holiday rentals in Chatham?
In Chatham, New York, there are numerous remote work holiday rentals available, with around 64 options to choose from. This charming town, located in the scenic Berkshire Hills, offers a tranquil environment great for those looking to balance work and leisure. Many of the properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated workspaces with desk chairs, and comfortable living areas to help you stay productive during your stay.The area is also rich in natural beauty, providing opportunities for outdoor activities such as hiking and exploring local parks. Nearby, you'll find quaint shops, cafes, and restaurants that add to the local charm. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Chatham?
In Chatham, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature outdoor decks or patios, superb for enjoying the serene surroundings. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, rentals often provide coffee and tea makers, ensuring that guests can enjoy a warm beverage at their leisure.
When is the best time to visit Chatham for a holiday rental?
The best time to book a holiday rental in Chatham is during the peak season, which runs from July to September. This vibrant period attracts visitors seeking a delightful summer getaway filled with outdoor activities, including hiking, boating, and exploring the charming local shops and restaurants. July, in particular, is the most popular month, when the warm weather (averaging around 20 to 30 degrees Celsius) creates a great backdrop for enjoying the stunning landscapes and cultural events that Chatham has to offer.During these months, you can expect a lively option, with numerous festivals and events that highlight the local culture. Families and friends often gather to take advantage of the long, sunny days, making it an ideal time for group outings and making lasting memories.If you're looking for a more budget-friendly experience, consider visiting in November. While this month may be quieter, it offers a unique charm, with peaceful landscapes and the opportunity to enjoy Chatham's beauty without the crowds. You can take leisurely walks through the fall scenery, often accompanied by crisp air and beautiful autumn colours.Ultimately, the best time to visit Chatham will depend on whether you prefer the lively summer buzz or the tranquil beauty of the late autumn.
What are the top attractions in Chatham?
In Chatham, New York, visitors can enjoy a variety of attractions that showcase the charm of this small town and its surrounding natural beauty. The Chatham Village Historic District features quaint streets lined with well-preserved 19th-century buildings, providing a picturesque setting for leisurely strolls. The Chatham Arts Council often hosts events and exhibitions, making the arts a vibrant part of the community.For nature enthusiasts, the nearby Taconic State Park offers ample opportunities for hiking, birdwatching, and picnicking amidst stunning landscapes. The park's diverse trails cater to all skill levels, making it a superb spot for outdoor activities.Additionally, the Chatham Farmers' Market is a local highlight, where visitors can sample fresh produce and artisanal goods while soaking up the community atmosphere.
Are all fees included in the Chatham holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chatham holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chatham with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chatham holiday homes?
You can find great discounts on holiday homes in Chatham on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chatham holiday home booking on Stayz?
To find Chatham holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chatham?
A long-stay holiday home in Chatham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chatham holiday home?
Book your Chatham holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chatham?
Prices for holiday homes in Chatham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chatham to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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