Chatham holiday homes

We found 1,301 holiday rentals — enter your dates for availability
Discover a selection of 11 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:25 Dec - 1 Jan

Property grounds
Private kitchen
Living area
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
NZ$15,164
for 7 nights, 1 home
NZ$2,166 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Open plan dining area with water views and access to the sunroom
view from the 2nd bedroom
View of the lower deck from the sunroom
View from the lawn by the water
Exceptional
(66 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$10,200
for 7 nights, 1 home
NZ$1,457 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Dining
Terrace/patio
Interior
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
NZ$4,306
for 7 nights, 1 cottage
NZ$615 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
3 season Sunroom
Property grounds
House 1- Mountain views from this open concept kitchen, dining, sitting room
Dining area and small sitting are with flat screen TV. Stairs to second floor
Exceptional
(7 reviews)

Grand Estate w/ Mountain Views by Evergreen Home

Ghent

11% off
NZ$12,029
for 7 nights, 1 home
NZ$1,718 per night
includes taxes & fees
Grand Estate w/ Mountain Views by Evergreen Home
Outdoor dining
Exterior detail
Interior
Interior
Exceptional
(71 reviews)

Beautiful Modern Swiss Cottage in Athens, NY

Athens

12% off
NZ$5,011
for 7 nights, 1 home
NZ$716 per night
includes taxes & fees
Beautiful Modern Swiss Cottage in Athens, NY
Sleepy Hollow Lake
Kitchen
Dining room
Living room
Exceptional
(5 reviews)

Spacious Lake Community House near Hudson

Athens

9% off
NZ$8,322
for 7 nights, 1 home
NZ$1,189 per night
includes taxes & fees
Spacious Lake Community House near Hudson
Property grounds
Outdoor spa tub
Living area
From kitchen. Vintage bar contains cocktail glasses and shaker.
Exceptional
(28 reviews)

Modern, Minimalist, Light-filled Home with Hot Tub Near Hudson

Craryville

8% off
NZ$8,230
for 7 nights, 1 home
NZ$1,176 per night
includes taxes & fees
Modern, Minimalist, Light-filled Home with Hot Tub Near Hudson
Seamless entertaining with the wide open concept, living room -kitchen- patio
After a hard day on the trails or a long day on the town, relax in this oasis
Enjoy a beautiful crisp night under the lights
Never miss a thing with this expansive open concept kitchen and living room
Exceptional
(29 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

6% off
NZ$10,212
for 7 nights, 1 home
NZ$1,459 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Exterior detail
Living area
Interior
Interior
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$8,113
for 7 nights, 1 home
NZ$1,159 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Front Door entrance
Patio accessible from dining/kitchen
Pool
Double height, open kitchen and dining perfect for large vacation meals
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

6% off
NZ$8,809
for 7 nights, 1 home
NZ$1,258 per night
includes taxes & fees
Designer Home with Panoramic Views near Hudson
Dining
Interior
Exterior
Living area
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,890
for 7 nights, 1 cabin
NZ$699 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Private kitchen
Outdoor dining
Living area
Room
Exceptional
(11 reviews)

Glass Lake Cottage

Averill Park

8% off
NZ$6,322
for 7 nights, 1 home
NZ$903 per night
includes taxes & fees
Glass Lake Cottage
Property grounds
Terrace/patio
Screened in porch
Dining room with butcher block table
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

11% off
NZ$5,306
for 7 nights, 1 home
NZ$758 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Entrance into house with wood burning stove to right and staircase
View from 2nd floor balcony (after leaves have fallen)
Smart TV in Downstairs room with view of entrance to house and doors to room
Large Smart HDTV with electric fireplace in living room, showing dining room
Exceptional
(73 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Hancock

12% off
NZ$5,296
for 7 nights, 1 home
NZ$757 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Interior
Interior
Room
Exterior
Exceptional
(44 reviews)

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

Stephentown

8% off
NZ$2,998
for 7 nights, 1 home
NZ$428 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Main living room with a gas fireplace, generous seating, and expansive views.
Back of house with expansive windows, a covered deck, patio and beautiful views.
Lake views through the pine trees, with colorful foliage across the water.
Main living room with soaring windows overlooking the lake and wooded grounds.
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

15% off
NZ$5,623
for 7 nights, 1 home
NZ$803 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Alfresco dining
River view from window
Great room river view
Blue House side entry from driveway
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
NZ$5,215
for 7 nights, 1 home
NZ$745 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Living area
Living area
Living area
Interior
Excellent
(9 reviews)

The Race Mountain House

Sheffield

21% off
NZ$8,560
for 7 nights, 1 home
NZ$1,223 per night
includes taxes & fees
The Race Mountain House
Open Living Area
Two Tier Decking with Grill on Lower Deck
Kitchen and Dining Room
Room
Exceptional
(14 reviews)

Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights

Hillsdale

8% off
NZ$4,764
for 7 nights, 1 home
NZ$681 per night
includes taxes & fees
Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights
Open kitchen with south-facing windows
Front door of the guest suite
Backyard firepit
Pool is open June-Sept.
Exceptional
(17 reviews)

Le Soleil Suite - Pool, Mtn Views 10 Min To Hudson

Hudson

8% off
NZ$3,591
for 7 nights, 1 home
NZ$513 per night
includes taxes & fees
Le Soleil Suite - Pool, Mtn Views 10 Min To Hudson
Kitchen
Interior
Kitchen
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,871
for 7 nights, 1 home
NZ$982 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
We highly recommend the Sauna
Property grounds
Interior
Property grounds
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
NZ$4,394
for 7 nights, 1 home
NZ$628 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Private kitchen
Outdoor dining
Living area
Exterior
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
NZ$5,008
for 7 nights, 1 home
NZ$715 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Welcome Home!
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!
Private kitchen
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
NZ$6,006
for 7 nights, 1 home
NZ$858 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)
  • Kennedy Park (16.3 mi / 26.2 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)

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:

  • 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)
  • Lenox Mountain (15 mi / 24.1 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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Chatham holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Chatham to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.