Canaan Holiday Rentals

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Holiday Rentals in Canaan

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
The price is AU$494
includes taxes & fees
2 Nov - 3 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
8.6 out of 10, Excellent, (26)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
The Goshen Glass Chalet
9.6 out of 10, Exceptional, (40)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
The Goshen Glass Chalet
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
The price is AU$1,231
includes taxes & fees
22 Oct - 23 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (228)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Peace and quiet on the lake
9.6 out of 10, Exceptional, (226)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.6 out of 10, Exceptional, (15)
"We came for a concert at Tanglewood. Property was just as photos described, walking distance to downtown Lee restaurants, easy access to highway and other towns. Great spot for multiple family or friends to get together."
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Stay Lakeside This Summer!
9.8 out of 10, Exceptional, (77)
"Beautiful lake views, comfy and cozy house! We had a wonderful time. Thank you for sharing your home with us. "
Stay Lakeside This Summer!
Summer Lake Cottage, private beach, Berkshire Hills, small village
9.4 out of 10, Exceptional, (83)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Lakefront Fall Foliage in New England Just 2 Hours From NYC
10.0 out of 10, Exceptional, (86)
"Great location and fully equipped cabin! I hope to return sometime soon Everything was perfect!"
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is AU$1,110
includes taxes & fees
26 Oct - 27 Oct
Guesthouse Cabin vacation rentals in Berkshire County
Private Island - Largest Fresh Water Reservoir in Mass
8.6 out of 10, Excellent, (9)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Antique Farmhouse Totally Restored
9.8 out of 10, Exceptional, (92)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (11)
"Everything was great...and beautiful!"
The price is AU$627
includes taxes & fees
22 Oct - 23 Oct
The Blue Elm - A Historic Berkshire Cottage
The Studio mini home away from home in the Berkshires
9.6 out of 10, Exceptional, (29)
"Great place to stay in Berkshires."
The Studio mini home away from home in the Berkshires
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
9.8 out of 10, Exceptional, (23)
"Farmhouse was as pictured and very clean. Grounds and location were gorgeous "
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
10.0 out of 10, Exceptional, (158)
"The location was beautiful. Directions for parking and access to enter were clear. The house felt more like someone’s personal residence than a vacation rental. There were clothes in the closets, food left in the kitchen and no iron and ironing board. The mattresses sagged so we all rolled to the middle when sleeping. With some furniture updates and better cleaning to address the musty smell, cobwebs and ants, this could be a gem."
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is AU$619
includes taxes & fees
29 Oct - 30 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Stunning Renovated Victorian
10.0 out of 10, Exceptional, (54)
"Really loved the property! Was returning to Great Barrington for a reunion of sorts. The house was a perfect spot to relax and reconnect. The space is very well appointed. The fab kitchen and outdoor / porch areas were perfect for the occasion. Very peaceful and welcoming place. We were a group of ladies in our 40s, but well stocked with things for littles as well. Highly recommended!"
Stunning Renovated Victorian
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Canaan Hotel Reviews

Find out more about Canaan

Everything you need to know about Canaan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Canaan holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Canaan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Canaan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Canaan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Canaan holiday rentals we have selected for you start as low as AU$494 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Canaan rentals

At Expedia, we put the best Canaan holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Canaan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Canaan holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Canaan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Canaan?

Yes, there are holiday rentals close to the most popular sights in Canaan, or you can select a more secluded option if you're looking for a relaxing stay. Canaan is known for its restaurants and coffee shops.

What are some of the best holiday rentals that Canaan has to offer?

Lakefront Fall Foliage in New England Just 2 Hours From NYC: This holiday home rental outside of Canaan is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a private garden and a selection of games.

How many holiday rentals are there in Canaan?

Expedia has 5 holiday rentals for your stay in Canaan.

What’s there to see and do in Canaan?

Housatonic River and Edith Scoville Memorial Sanctuary are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Campbell Falls State Park and North Canaan Town Hall.

What’s a holiday rental in Canaan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Canaan. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.