Photo by Robin/Loving Life

Canaan holiday rentals

We found 526 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Canaan that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Canaan

Showing deals for:18 Dec - 25 Dec

Open plan dining area with water views and access to the sunroom
view from the 2nd bedroom
View from the lawn by the water
Workstation with a view!
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$8,017
for 7 nights, 1 home
AU$1,145 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior
Private kitchen
Terrace/patio
Property grounds
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$7,940
for 7 nights, 1 home
AU$1,134 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Welcome!
Property grounds
House 1- Mountain views from this open concept kitchen, dining, sitting room
3 season Sunroom
Exceptional
(7 reviews)

Grand Estate w/ Mountain Views by Evergreen Home

Ghent

11% off
AU$9,450
for 7 nights, 1 home
AU$1,350 per night
includes taxes & fees
Grand Estate w/ Mountain Views by Evergreen Home
Outdoor dining
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,358
for 7 nights, 1 home
AU$908 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Dining
Interior
Living area
Property grounds
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,807
for 7 nights, 1 cabin
AU$544 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Front Staircase
Fully screened porch!
Dining Room w/ Doors to Screened Porch Dining Area
Reading nook with natural lighting
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
AU$5,189
for 7 nights, 1 home
AU$741 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Room
Interior
Interior
Living area
Exceptional
(42 reviews)

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

Stephentown

8% off
AU$2,406
for 7 nights, 1 home
AU$344 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Views from the back of the 16 acres on the property
View from 2nd floor balcony (after leaves have fallen)
Smart TV in Downstairs room with view of entrance to house and doors to room
Entrance into house with wood burning stove to right and staircase
Exceptional
(73 reviews)

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

Williamstown

12% off
AU$3,569
for 7 nights, 1 home
AU$510 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Screened in porch
Terrace/patio
Queen bedroom
Property grounds
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

9% off
AU$3,990
for 7 nights, 1 home
AU$570 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Alfresco dining
River view from window
Blue House side entry from driveway
dining area
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
AU$3,843
for 7 nights, 1 home
AU$549 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Interior
Interior
Property grounds
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,447
for 7 nights, 1 home
AU$778 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Living area
Living area
Living area
Private kitchen
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

8% off
AU$5,529
for 7 nights, 1 home
AU$790 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
Interior
Spring at Jiminy Peak 2019
Night skiing view from living room
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

13% off
AU$12,746
for 7 nights, 1 home
AU$1,821 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Coming up the path from down by the creek
Property grounds
Exterior
Living room
Exceptional
(13 reviews)

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

8% off
AU$2,958
for 7 nights, 1 home
AU$423 per night
includes taxes & fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
another view of same bedroom as well as makeup table
new backyard table
another view of kitchen
kitchen and laundry room area
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

23% off
AU$5,050
for 7 nights, 1 apartment
AU$721 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Room
Interior
Interior
Exterior
Exceptional
(6 reviews)

Chatham Cozy Country Retreat

Chatham

7% off
AU$2,006
for 7 nights, 1 apartment
AU$287 per night
includes taxes & fees
Chatham Cozy Country Retreat
Property grounds
Living area
Room
Interior
Exceptional
(40 reviews)

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville

7% off
AU$1,986
for 7 nights, 1 home
AU$284 per night
includes taxes & fees
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Interior
Dining
Entry and living room
Living Room, wow!
Exceptional
(17 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
AU$3,513
for 7 nights, 1 apartment
AU$502 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Dining
Private kitchen
Gorgeous open concept living room
Quarter & Rift sawn white oak floors
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
AU$7,389
for 7 nights, 1 apartment
AU$1,056 per night
includes taxes & fees
The Penthouse, Downtown Lenox 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

The trendy city of Canaan awaits you

Enjoy the museums and other features of Canaan. Well known for its restaurants, shopping and local tours, this trendy city won't disappoint. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Canaan

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

  • Bousquet Ski Area (8.5 mi / 13.8 km)
  • Wyndhurst Golf & Club (10.3 mi / 16.6 km)
  • Jiminy Peak Mountain Resort (12.7 mi / 20.4 km)
  • Catamount Ski Area (17 mi / 27.4 km)
  • Ski Butternut (17.1 mi / 27.5 km)
  • Furnace Brook Winery at Hilltop Orchards (3.4 mi / 5.4 km)

Exploring the natural features in Canaan

Whether you're an active traveller or just want to take in the scenery, Canaan is a great spot to appreciate mother nature. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Lenox Mountain (7.2 mi / 11.6 km)
  • Stockbridge Bowl (8.4 mi / 13.5 km)
  • Berkshire Botanical Garden (9.5 mi / 15.3 km)
  • The Mount (9.9 mi / 15.9 km)
  • Naumkeag Museum (10.8 mi / 17.3 km)
  • Kinderhook Lake (11.1 mi / 17.8 km)

Travelling to and around Canaan

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 8 mi (12.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Hudson, NY (HCC-Columbia County), which is 15.8 mi (25.4 km) away.

Frequently asked questions

What is the best area to stay in Canaan when booking a holiday rental?
When considering a holiday rental in Canaan, New York, a popular area to stay is near the charming village centre. This location offers a delightful mix of tranquillity and accessibility to local attractions. You can easily explore the scenic beauty of the surrounding countryside, known for its rolling hills and lush landscapes.In addition to its natural splendour, visitors can enjoy nearby attractions such as the picturesque Catamount Ski Area, which is great for winter sports enthusiasts, and the renowned Olana State Historic Site, the former home of artist Frederic Edwin Church. The village centre has a limited number of properties available, providing a cosy and inviting atmosphere that caters well to those seeking a peaceful getaway.
Where are the best Canaan ski resort rentals?
For the best ski resort rentals near Canaan, New York, travellers should focus on the nearby area of Catamount Ski Area, located just a short drive away. In the charming towns of Canaan and Great Barrington, visitors can find a selection of cosy cabins and comfortable holiday homes that cater to winter sports enthusiasts. Many of these properties come equipped with essential amenities such as full kitchens, fireplaces, and spacious living areas, superb for unwinding after a day on the slopes.In Great Barrington, which is renowned for its vibrant arts scene and local dining options, you can discover rentals that feature modern comforts, including Wi-Fi and outdoor spaces for relaxation. Some accommodations may also offer easy access to the area's hiking trails, allowing guests to explore the beautiful surroundings in the off-season.Additionally, the nearby town of Lee provides further options, with properties that often boast picturesque views of the Berkshires. These homes typically include amenities like hot tubs and outdoor decks, ideal for enjoying the winter landscape.
What is the most popular type of holiday rental accomodation in Canaan?
In Canaan, holiday houses are the most popular type of holiday rental, with about 14 available throughout the area. These properties typically offer spacious living areas, fully equipped kitchens, and outdoor spaces for enjoying the serene surroundings. Additionally, there are several cottages, chalets, and cabins that provide a rustic charm and a cosy atmosphere, ideal for those seeking a peaceful retreat in nature. Many of these rentals come with amenities such as fireplaces, BBQ facilities, and easy access to local hiking trails and lakes, making Canaan an appealing destination for families and groups looking for a comfortable getaway.
Are there any family house rentals in Canaan?
In Canaan, New York, there are several family-friendly house rentals available, with around 11 options to choose from. This picturesque area is great for groups seeking a blend of outdoor adventure and relaxation. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play freely.Visitors can explore the nearby scenic attractions, including the beautiful landscapes of the Berkshires and the serene lakes great for summer activities. Many homes also offer amenities such as Wi-Fi and comfortable furnishings, ensuring a pleasant stay for families.
Can I rent a holiday home with a pool or hot tub in Canaan?
In Canaan, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for travellers seeking relaxation. This picturesque area offers a tranquil setting, with many properties located amidst beautiful landscapes, ideal for families or groups looking to unwind.Accommodations often include amenities such as private pools, hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens for convenient self-catering. Some rentals may also provide additional features like outdoor barbecue facilities and scenic views, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Canaan?
In Canaan, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to bring their furry companions along. Many of these properties come equipped with amenities such as spacious yards, fully stocked kitchens, and cosy living areas, ensuring a comfortable stay.The area is known for its scenic beauty, with opportunities for outdoor activities that are superb for pets, such as hiking in the nearby Berkshire Mountains and exploring the local parks. Additionally, Canaan's charming rural atmosphere provides a peaceful retreat, allowing visitors to enjoy both relaxation and adventure.
Are there any remote work holiday rentals in Canaan?
In Canaan, New York, there are approximately 26 holiday rentals suitable for remote work. This charming area offers a serene environment, making it an ideal location for those looking to blend work and leisure. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas to ensure a productive stay.Travellers can explore the picturesque landscapes and local attractions during their downtime, with opportunities for hiking and enjoying nature nearby. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Canaan?
In Canaan, popular holiday rental amenities include well-equipped kitchens that allow guests to prepare their own meals, making it convenient for families or groups. Many rentals feature decks or patios, providing a lovely outdoor space to relax and enjoy the peaceful surroundings. A fireplace is a common amenity, adding a warm and cosy atmosphere, especially during the cooler months. For those who enjoy cooking, blenders are often available for making smoothies or other beverages. Additionally, onsite parking is typically provided, ensuring that guests have a straightforward experience when arriving by car.
When is the best time to visit Canaan for a holiday rental?
The best time to visit Canaan for a holiday rental is during the peak season, which runs from July to September. This vibrant period attracts visitors eager to enjoy the stunning landscapes, outdoor activities, and community events that Canaan has to offer. July, in particular, is the most popular month, bustling with tourists who come to experience the area's charm and natural beauty.During these summer months, temperatures typically hover around 20 to 30 degrees Celsius, creating ideal conditions for hiking, biking, and exploring the nearby parks. The pleasant weather allows for comfortable outdoor activities, whether you're strolling through local farmers' markets or enjoying a scenic picnic.If you're looking for a more budget-friendly option, consider visiting in December. This quieter month provides a unique opportunity to experience Canaan's winter wonderland, with beautiful snowy landscapes great for cozy getaways. While there may be fewer crowds, you can still enjoy the charm of the area and perhaps even partake in some seasonal festivities.
What are the top attractions in Canaan?
In Canaan, New York, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural heritage. The nearby Catamount Ski Area is a popular destination for winter sports enthusiasts, offering skiing and snowboarding in the colder months, while in the summer, it transforms into a hub for mountain biking and hiking.For those who appreciate the arts, the town is close to the charming town of Chatham, which features the Chatham Historic Depot and the local art galleries showcasing works by regional artists. The Canaan and surrounding areas are also known for their scenic landscapes, making it a great spot for outdoor activities such as hiking and birdwatching, particularly in the nearby parks and nature reserves.Additionally, the area is home to several local farms that offer seasonal produce and events, allowing visitors to experience the rural charm of the Berkshires. For a taste of local history, the nearby town of Great Barrington features historic sites and a vibrant downtown with shops and restaurants.
Are all fees included in the Canaan 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 Canaan holiday homes with parking?
Stayz offers a wide selection of holiday homes in Canaan 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 Canaan holiday homes?
You can find great discounts on holiday homes in Canaan 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 Canaan holiday home booking on Stayz?
To find Canaan 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 Canaan?
A long-stay holiday home in Canaan 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 Canaan holiday home?
Book your Canaan 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 Canaan?
Prices for holiday homes in Canaan 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 Canaan 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.