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Canaan holiday lettings

We found 570 holiday rentals — enter your dates for availability

Discover a selection of 13 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:13 Feb - 20 Feb

Image gallery for Berkshires Colonial on 2 Acres by Evergreen Home

Fully screened porch!
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond, MA

12% off
Price is £2,923
for 7 nights, 1 home
£418 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home

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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)
  • 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 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:

  • 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)

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, the area around the picturesque Canaan Valley is an excellent choice. This neighbourhood offers a tranquil retreat, surrounded by beautiful landscapes and lush greenery, making it ideal for those looking to unwind in nature. The Canaan Valley State Forest is a prominent attraction nearby, where visitors can enjoy hiking, birdwatching, and picnicking amidst the serene environment.

Another appealing area to consider is the vicinity of the Canaan Historic District, which boasts charming architecture and a rich history. Here, you can explore local shops and eateries that reflect the area's heritage while taking in the quaint atmosphere. The proximity to the Catamount Ski Area also makes this location attractive for winter sports enthusiasts, providing a variety of activities throughout the year.
How much does it cost to rent a holiday home in Canaan?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Canaan holiday 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 approximately 20 minutes away and offers a variety of rental options. In Great Barrington, visitors can find charming cabins and modern condos that provide easy access to the slopes at Catamount Ski Area. Many of these properties come equipped with amenities such as fully equipped kitchens, spacious living areas, and outdoor decks, ideal for relaxing after a day of skiing.

Additionally, the town of Pittsfield, located nearby, offers more rental choices, including cosy homes with fireplaces and large living spaces for families or groups. Properties here often feature amenities like hot tubs, game rooms, and proximity to local dining and shopping, enhancing the overall experience for travellers.
What is the most popular type of holiday rental accomodation in Canaan?
In Canaan, holiday houses are the most popular type of rental, with about 15 available in the area. These houses are typically set in serene locations, offering a spacious environment ideal for families or groups. Most feature amenities such as fully equipped kitchens, multiple bedrooms, and outdoor spaces, which are great for barbecues or simply enjoying the tranquil surroundings. Additionally, there are several cottages, chalets, apartments, and cabins, providing a variety of options for travellers.
Are there any family house rentals in Canaan?
In Canaan, New York, there are numerous family-friendly house rentals available, with about 14 options to choose from. This picturesque area offers a blend of scenic beauty and outdoor activities, making it a great choice for families. Many of these homes provide spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and explore.
Can I rent a holiday home with a pool or hot tub in Canaan?
In Canaan, New York, there are several holiday homes available for rent that feature pools and hot tubs, making it a lovely destination for relaxation. The area offers a mix of charming rural properties and modern homes, often located amidst picturesque landscapes. Travellers can expect amenities such as private pools, hot tubs, spacious gardens, and outdoor seating areas, great for enjoying the serene surroundings. Many rentals also include fully equipped kitchens, allowing guests to prepare meals at their convenience.
Can I find long-stay holiday rentals in Canaan?
A long-stay holiday 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, there are several pet-friendly house rentals available, great for travellers wishing to bring their furry companions along. The area offers a variety of charming properties, including rustic cabins and cosy homes that often come with amenities such as fully equipped kitchens, outdoor decks, and spacious living areas, ensuring a comfortable stay for both humans and pets.
Are there any remote work holiday rentals in Canaan?
In Canaan, New York, there are several remote work-friendly holiday rentals available, with around 15 options to choose from. This picturesque area is great for those wishing to combine work with leisure, offering a tranquil environment surrounded by nature. Many properties cater specifically to remote workers, featuring essential amenities such as Wi-Fi, dedicated workspaces with desks and ergonomic chairs, and sometimes even additional equipment like computer monitors to ensure a productive stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Canaan holiday rentals with parking?
Vrbo offers a wide selection of holiday 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 holiday 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 holiday rental?
July marks the most popular time to visit Canaan, as summer brings a vibrant atmosphere ideal for outdoor enthusiasts. From July to September, the region buzzes with activity, attracting families and adventure seekers eager to enjoy hiking, cycling, and various festivals. The warm temperatures, often reaching the low 30s Celsius, create great conditions for exploring the area's scenic trails and engaging in water activities at nearby lakes.

In July, Canaan truly comes alive, with many visitors taking advantage of the long days and lively events. The local calendar is filled with farmers' markets, outdoor concerts, and art festivals, providing ample opportunities to immerse yourself in the community while enjoying the picturesque surroundings.

For travellers seeking a more budget-friendly experience, visiting in December can be a delightful alternative. While this month is quieter, it offers a unique charm, with the region's natural beauty enhanced by a dusting of snow, great for cosy indoor experiences or winter sports at nearby resorts.
How early should I book a Canaan holiday rental?
Book your Canaan holiday 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 holiday 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 holiday 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 holiday 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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