Canaan holiday rentals

We found 185 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Canaan that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Canaan

Showing deals for:20 Nov - 27 Nov

It’s cool on the screened porch
You, the moon, the fire pit…..,
2 car garage—ping pong and bikes.
Dining
Exceptional
(191 reviews)

“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

Sheffield

8% off
AU$3,061
for 7 nights, 1 home
AU$437 per night
includes taxes & fees
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
Exterior
Private kitchen
Living area
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Southfield

8% off
AU$9,085
for 7 nights, 1 home
AU$1,298 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Interior
Property grounds
Property grounds
After a day in the snow
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
AU$3,503
for 7 nights, 1 home
AU$500 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Interior
Living area
Living area
Living area
Exceptional
(7 reviews)

The Race Mountain House

Sheffield

35% off
AU$5,395
for 7 nights, 1 home
AU$771 per night
includes taxes & fees
The Race Mountain House
Property grounds
Interior
Living area
Dining
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
AU$5,650
for 7 nights, 1 cabin
AU$807 per night
includes taxes & fees
Guesthouse Cabin vacation rentals in Berkshire County
Patio off kitchen
Kitchen
Kitchen open to living room
2nd bedroom
Exceptional
(77 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

Great Barrington

8% off
AU$2,304
for 7 nights, 1 cottage
AU$329 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
kitchen
Front Entrance
dining room
Interior
Exceptional
(15 reviews)

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Sheffield

8% off
AU$6,036
for 7 nights, 1 home
AU$862 per night
includes taxes & fees
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Private kitchen
Living area
Outdoor dining
Pool
Exceptional
(5 reviews)

Lakeville Lodge with Private Pool – Walkable to Lake, Restaurants, & Salisbury!

Lakeville

8% off
AU$4,609
for 7 nights, 1 home
AU$658 per night
includes taxes & fees
Lakeville Lodge with Private Pool – Walkable to Lake, Restaurants, & Salisbury!
Private kitchen
Living area
Exterior
Bathroom
Exceptional
(32 reviews)

Two Bedroom Cottage Close To Town

Sharon

6% off
AU$3,144
for 7 nights, 1 cottage
AU$449 per night
includes taxes & fees
Two Bedroom Cottage Close To Town
Game, puzzle and play table - plenty of chairs.
Porch opens up from dining room. Ceiling fan and lights above.
Entrance view.
View of the river.
Exceptional
(42 reviews)

Converted Berkshire schoolhouse on a quiet river

Great Barrington

8% off
AU$2,846
for 7 nights, 1 home
AU$407 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river

  • 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 friendly city of Canaan awaits you

The countryside and surrounding scenery provide a peaceful ambience to your holiday home in Canaan. Travellers appreciate the restaurants in this welcoming city. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Canaan

Are you searching for things to do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Canaan a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (10.8 mi / 17.4 km)
  • Catamount Ski Area (13 mi / 21 km)
  • Mohawk Mountain Ski Area (13.2 mi / 21.2 km)
  • Otis Ridge (15.8 mi / 25.4 km)
  • Trevor Zoo (19.7 mi / 31.8 km)
  • Land of Nod Vineyard and Winery (1.1 mi / 1.8 km)

Exploring the natural landscape of Canaan

Whether you're looking for adventure or just want to appreciate the scenery, Canaan is a great place to spend some time outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Great Falls (5.4 mi / 8.7 km)
  • Mount Frissell (6.6 mi / 10.7 km)
  • Lake Buel (10 mi / 16.1 km)
  • Harlem Valley Rail Trail (11.6 mi / 18.6 km)
  • Housatonic River Walk (12.1 mi / 19.5 km)
  • Housatonic River (12.1 mi / 19.5 km)

How to get to and around Canaan

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 27.6 mi (44.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Hudson, NY (HCC-Columbia County), which is 27.8 mi (44.7 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, Connecticut, the area around the charming village centre is an excellent choice. This picturesque neighbourhood offers a quaint atmosphere, making it ideal for visitors looking to enjoy a serene getaway. Here, you can find a delightful selection of properties, ranging from cosy cottages to spacious homes that cater to various group sizes.One of the highlights of staying in this area is the proximity to the stunning Appalachian Trail, great for hiking enthusiasts seeking scenic views and outdoor adventures. Additionally, the nearby Catamount Ski Area provides a fantastic option for winter sports lovers, ensuring that there's always something to do regardless of the season.
Where are the best Canaan ski resort rentals?
For renting near Canaan ski resort, visitors should consider the charming community of Canaan itself, which offers a variety of rental options suited for winter sports enthusiasts. Many properties in this area are cozy cabins or chalets, often featuring amenities such as wood-burning stoves, fully equipped kitchens, and spacious living areas ideal for relaxing after a day on the slopes. Some rentals may also offer hot tubs, great for soothing sore muscles.Adjacent to Canaan, the nearby town of Salisbury is another excellent option, providing additional rental properties with easy access to the ski resort. Here, you can find comfortable homes that often include amenities like outdoor decks with scenic views, fireplaces, and proximity to local dining and shopping options, enhancing the overall experience.Moreover, the picturesque landscapes surrounding Canaan provide opportunities for cross-country skiing and snowshoeing, with rental properties typically located near trails that cater to these activities.
What is the most popular type of holiday rental accomodation in Canaan?
In Canaan, holiday houses are the predominant type of holiday rental, with around 10 available throughout the area. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups looking for a comfortable stay. Many of these properties also come with outdoor spaces, allowing guests to enjoy the picturesque surroundings of the Connecticut countryside.
Are there any family house rentals in Canaan?
In Canaan, Connecticut, there are several family-friendly house rentals available, making it an inviting destination for those travelling with children. Visitors can find homes that offer spacious living areas, ideal for family gatherings, along with fully equipped kitchens superb for preparing meals together. Many properties include outdoor spaces where children can play and enjoy the fresh air.The surrounding area boasts beautiful landscapes, including nearby state parks and walking trails, superb for family outings. Additionally, Canaan is conveniently located close to local attractions like the scenic Berkshire Mountains, where outdoor activities such as hiking and biking await.
Can I rent a holiday home with a pool or hot tub in Canaan?
In Canaan, Connecticut, there are several holiday homes available for rent that come with pools or hot tubs, providing excellent options for relaxation and leisure. This picturesque town, set in the scenic Berkshires region, offers a peaceful retreat with a variety of amenities in its rental properties.Travellers can expect many of these homes to feature private pools, inviting hot tubs, spacious outdoor areas, and fully equipped kitchens suitable for family gatherings or entertaining friends. Additionally, some rentals may include features like fire pits, barbecues, and beautiful gardens, superb for enjoying the natural surroundings.
Are there pet-friendly house rentals in Canaan?
In Canaan, Connecticut, there are several pet-friendly house rentals available for travellers seeking a getaway. The area offers a charming rural setting with various holiday homes that typically feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Many properties also include features like fireplaces, making them cosy retreats during colder months.Canaan's picturesque surroundings provide opportunities for outdoor activities, with nearby parks and trails that are great for walking or hiking with pets.
Are there any remote work holiday rentals in Canaan?
In Canaan, Connecticut, there are about 10 remote work holiday rentals available for those seeking a productive getaway. The area offers a serene environment, great for focusing while surrounded by nature. Many properties feature essential amenities such as free Wi-Fi, allowing for seamless connectivity during your stay. Expect comfortable living spaces equipped with desks or dedicated work areas, ensuring a conducive atmosphere for remote work.Canaan is located in the beautiful Litchfield Hills region, known for its outdoor recreational opportunities, including hiking trails and scenic views. After work hours, you can explore local attractions or unwind in the tranquility of this charming town. 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, which allow guests to prepare their own meals during their stay. Many properties also feature inviting decks or patios, great for enjoying the fresh air and picturesque surroundings. Travellers can expect to find amenities such as blenders for making smoothies or other beverages, as well as cosy fireplaces that add warmth and charm to the living spaces. Additionally, porches or lanais provide a lovely spot to relax and take in the views.
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 from June to August. This period is particularly popular as visitors flock to enjoy the vibrant summer activities that the area has to offer. With warm temperatures averaging between 20 and 30 degrees Celsius, it's an ideal time for outdoor adventures such as hiking in the nearby mountains or enjoying leisurely walks through the charming town.July is the highlight of the summer season, attracting many families and outdoor enthusiasts who appreciate the lively option and the variety of local events. The lush greenery and picturesque landscapes provide a great backdrop for sightseeing and recreational activities, ensuring that your days are filled with exploration and enjoyment.For those looking for a more budget-friendly option, consider planning your visit in December. While this month falls outside the high tourist season, it offers a unique charm with potential winter activities and a quieter atmosphere, allowing you to appreciate the serene beauty of Canaan during the holiday season.Ultimately, the best time for your visit will depend on whether you prefer the bustling summer vibe with its plentiful outdoor pursuits or a more peaceful retreat in the winter months.
What are the top attractions in Canaan?
In Canaan, Connecticut, visitors can enjoy a variety of attractions that highlight the area's natural beauty and charm. The nearby Housatonic River offers opportunities for fishing, kayaking, and scenic walks along its banks. For those interested in hiking, the Appalachian Trail runs close by, providing stunning views and outdoor adventure.The town itself features a quaint downtown area where visitors can explore local shops, cafés, and restaurants, giving a taste of the community's character. Additionally, the picturesque landscapes surrounding Canaan are great for leisurely drives or cycling, especially during the fall when the foliage is vibrant. For a more cultural experience, the nearby town of Salisbury hosts events and activities at the Salisbury Artisans, an eclectic collective of local artists.
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.

More holiday ideas