Canaan Holiday Rentals

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Holiday Rentals in Canaan

Holiday Home in Canaan

10.0 out of 10, Exceptional, (13)
"Clean, well equipped, updated kitchen, bathrooms. Appreciated the bidets. Host was wonderful to deal with. "
United States
Jane P.
Villa Mariana Blackberry River. Luxury, pool, comfort, peaceful nature, updated

Apartment in Great Barrington

9.6 out of 10, Exceptional, (38)
"Great location, spacious and well equipped "
United Kingdom
Alison F.
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Holiday Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is AU$460
includes taxes & fees
2 Dec - 3 Dec
Pet Friendly Riverfront Home in Great Barrington

Holiday Home in Sherwood Forest

9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake

Holiday Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$581
includes taxes & fees
2 Dec - 3 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Holiday Home in Great Barrington

10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Cabin in Northwest Harwinton

8.6 out of 10, Excellent, (27)
"Love the place.. very clean ..loved the neighbors.. got to catch up on well needed rest.. the neighbors on the right were wonderful than the owners came and they were also wonderful also"
United States
Andrea m.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Cabin in Sherwood Forest

9.6 out of 10, Exceptional, (231)
"We appreciated how clean and well stocked the cottage was. The owner was very easy to work with. Accurate description of a quiet, secluded get-away in the woods "
United States
Roberta F.
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Holiday Home in Lee

8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AU$1,147
includes taxes & fees
8 Dec - 9 Dec
Spacious 5-bedroom house in charming Lee with WiFi

Chalet in Becket

9.6 out of 10, Exceptional, (20)
"Beautiful property, very clean.. excellent place!"
United States
jason g.
Little Longbow Lakefront Chalet

Holiday Home in Copake

9.8 out of 10, Exceptional, (14)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
United States
Melissa D.
Remodeled Lakefront retreat!!! Don't forget to book for ski season!

Holiday Home in Stockbridge

10.0 out of 10, Exceptional, (104)
"Great house with gracious and responsive hosts. Everything in working order and the houseclean and grand."
United States
David H.
A Grand property in Historic Stockbridge

Apartment in Lee

9.4 out of 10, Exceptional, (71)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Holiday Home in Cornwall

9.6 out of 10, Exceptional, (53)
"Great house and great stay!"
United States
Timothy P.
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent

Holiday Home in Sheffield

9.8 out of 10, Exceptional, (93)
"The property was beautiful. Very spacious, inside and out. "
United States
Michelle C.
Antique Farmhouse Totally Restored

Cottage in Sheffield

10.0 out of 10, Exceptional, (15)
"It was wonderful!! The hosts were fantastic and the place was lovely. Highly recommend. "
United States
noel s.
The Blue Elm - A Historic Berkshire Cottage

Holiday Home in Egremont

9.8 out of 10, Exceptional, (25)
"Farmhouse was as pictured and very clean. Grounds and location were gorgeous "
United States
kathy l.
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Holiday Home in Great Barrington

10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Holiday Home in Barkhamsted

10.0 out of 10, Exceptional, (3)
"It's a wonderful house, lots of space to visit with family and the bed rooms were confortable and cozy. The host was very helpful and accesible at all times."
Spain
Heather A.
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Holiday Home in Goshen

9.6 out of 10, Exceptional, (41)
"The place was very nice met all of our expectations. "
United States
Marie G.
The Goshen Glass Chalet
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$460 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?

Pet Friendly Riverfront Home in Great Barrington: This holiday home rental outside of Canaan is located on a river, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as 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 Beckley Furnace Industrial Park 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 Edith Scoville Memorial Sanctuary.

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.