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Canaan vacation rentals

We found 584 vacation rentals — enter your dates for availability

Discover a selection of 16 homes and other vacation rentals in Canaan that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the best amenities for spending time at your vacation home, such as parking and air conditioning. You'll be able to choose a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Canaan

Showing deals for:Nov 21 - Nov 28

Image gallery for Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Exterior
10 out of 10 rating
Exceptional
(6 reviews)

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Stockbridge, MA

10% off
Price is CA $1,343
CA $11,730 total
includes taxes & fees
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

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Find out more about Canaan

Find out more about Canaan

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 vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation 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 hoping to find things to do in the area? Venture out of your vacation home and check out everything that makes Canaan a fun spot to vacation. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Bousquet Ski Area (8.5 mi / 13.8 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)
  • Kennedy Park (9 mi / 14.4 km)

Exploring the natural features in Canaan

Whether you're an active traveler or just want to appreciate the scenery, Canaan is a great place to spend some time outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Queechy Lake (1.7 mi / 2.7 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)
  • Lake Mansfield Park (14.9 mi / 23.9 km)

Traveling to and around Canaan

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 8 mi (12.9 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying 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 vacation rental?
When considering a vacation rental in Canaan, New York, a delightful option is the area surrounding Canaan's quaint town centre. This charming neighbourhood offers a blend of rural tranquillity and easy access to local attractions. Staying here allows you to immerse yourself in the scenic beauty of the Berkshires, with opportunities for hiking and exploring nature.

A short drive away, you can visit the picturesque Catamount Ski Area, which provides excellent skiing in the winter and mountain biking in the summer. Additionally, the nearby town of Chatham, known for its lovely shops and restaurants, is just a stone's throw away, making it a superb spot for a leisurely afternoon stroll.
How much does it cost to rent a vacation home in Canaan?
Prices for vacation rentals 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. Vrbo offers something for every taste and budget, from affordable rentals in Canaan to more spacious homes.
Are there any discounts for Canaan vacation house rentals?
You can find great discounts on house rentals in Canaan on Vrbo, 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.
Where are the best Canaan ski resort rentals?
For the best ski resort rentals near Canaan, New York, travellers should consider the nearby town of Great Barrington, which is just a short drive away from the popular ski areas. Great Barrington offers a variety of rental options, including cosy cabins and modern chalets that cater to both couples and families. Many of these properties come with amenities such as fully equipped kitchens, spacious living areas with fireplaces, and outdoor decks that provide lovely views of the surrounding mountains.

Additionally, the nearby Catamount Ski Area, located in Hillsdale, is easily accessible and offers skiing and snowboarding for all skill levels. Rentals in the Great Barrington area often include features like ski storage, hot tubs, and proximity to local shops and restaurants, enhancing the overall experience for travellers.
What is the most popular type of vacation rental accomodation in Canaan?
In Canaan, vacation houses are the most popular type of accommodation, with about 15 available throughout the area. These properties provide spacious living arrangements and are often equipped with amenities such as fully equipped kitchens, comfortable seating areas, and outdoor spaces for relaxation. Additionally, several cottages, cabins, and apartments are available, each offering a unique charm and home-like feel. Cottages and cabins typically feature rustic designs and are situated in tranquil settings, ideal for those seeking a peaceful getaway.
Are there any family house rentals in Canaan?
In Canaan, New York, there are a variety of family-friendly vacation rentals available, with around 14 options to choose from. The area is known for its scenic beauty and outdoor activities, making it an excellent choice for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or enjoy a barbecue.
Can I rent a vacation home with a pool or hot tub in Canaan?
In Canaan, New York, there are several vacation homes available for rent that feature pools and hot tubs. This picturesque area, located in the Berkshires, offers a tranquil retreat with beautiful natural surroundings. Travellers can expect a variety of amenities in these rentals, including private pools, hot tubs for relaxation, and spacious outdoor areas ideal for gatherings or family fun. Many properties also include fully equipped kitchens, allowing guests to prepare their own meals after a day of exploring the outdoors.
Can I find long-stay vacation rentals in Canaan?
A long-stay vacation rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Canaan?
In Canaan, travellers will find several pet-friendly house rentals that cater to those wishing to bring their furry companions along. The area offers a variety of vacation homes equipped with amenities such as spacious backyards, fully stocked kitchens, and comfortable living areas, ideal for families or groups. Many properties also feature outdoor spaces where pets can enjoy the fresh air and play.
Are there any remote work vacation rentals in Canaan?
In Canaan, New York, there are several remote work vacation rentals available, with around 15 properties catering specifically to those needing a suitable workspace. Many of these rentals come equipped with essential amenities such as Wi-Fi, desk chairs, desks, and even computer monitors, ensuring that guests can comfortably work during their stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Canaan vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals 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 on Vrbo 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.
What are popular rental amenities in Canaan?
In Canaan, popular vacation rental amenities include fully equipped kitchens, which are essential for travellers looking to prepare their own meals. Many properties also feature patios, providing an outdoor space to relax and enjoy the serene surroundings. Additionally, rentals often come with cookware, dishware, and utensils, ensuring that guests have everything they need for dining in. Modern conveniences such as dishwashers and microwaves are commonly found, adding to the comfort and functionality of these accommodations.
When is the best time to visit Canaan for a vacation rental?
The best time to visit Canaan for a vacation rental is during the peak season from July to September. This vibrant period attracts families and outdoor enthusiasts eager to explore the stunning beauty of the Catskills. With warm temperatures averaging around 25°C, July stands out as the most popular month, offering a great backdrop for hiking, biking, and enjoying the local festivals that celebrate the area's rich culture.

As the summer sun shines down, visitors can revel in various outdoor activities, from scenic walks along the Hudson River to discovering the delightful local farms and artisan shops. The lively atmosphere during this peak season presents a great chance to immerse yourself in the community and connect with fellow travellers.

For those looking to enjoy Canaan at a more leisurely pace, consider planning your visit in December. Although this is typically the low season, the charm of the winter landscape can be magical, great for cosy retreats and enjoying the tranquillity of the area. You might even find some excellent deals on vacation rentals, allowing you to experience the serene beauty of snow-covered hills and festive local events without the summer crowds.
How early should I book a Canaan vacation rental?
Book your Canaan vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Canaan home rental booking on Vrbo?
To find Canaan vacation rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Canaan vacation rental prices shown on Vrbo?
Vrbo 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.

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