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Compare 84 Apartments in Canaan with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (8)
"Super cute, cozy and excellent location. Loved our stay. Will be back!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (60)
"Beautiful property with flower farm, pick your own berries and vegetable farm stand. Rustic log cabin feel with all amenities needed with kitchen."
The price is SAR 545
SAR 815 total
includes taxes & fees
20 Dec - 21 Dec
Cozy Rustic Apt in 18th c Berkshire Farmhouse

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (6)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (20)
"We had a lovely time at this large and welcoming condo. It was easy to find, had all the amenities we needed and was just the perfect place for an off-season get away. Would easily re-book at any time during the year. "
The price is SAR 590
SAR 1,197 total
includes taxes & fees
19 Dec - 20 Dec
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (31)
"The space was cozy and clean and the owners were very easy to communicate with and knowledgeable about the area. The bathroom has very fun lights. "
The price is SAR 545
SAR 815 total
includes taxes & fees
19 Dec - 20 Dec
Charming Apt in 18th c Berkshire Farmhouse

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

10.0 out of 10, Exceptional, (6)
"Comfortable and spacious, in a lovely setting. "
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Modern Copake Falls Getaway

9.8 out of 10, Exceptional, (28)
"Unbeatable accommodations, especially for the price. Would stay again, gorgeous sunrise and sunset, very peaceful. Wish I could live there part time!"
Modern Copake Falls Getaway

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

10.0 out of 10, Exceptional, (1)
"We stayed here because we had Tanglewood tickets which turned out to be a great stay… It was a beautiful drive getting there and close enough to Tanglewood. Our host gave wonderful advice on where to eat and places to go. Thanks so much for sharing your place with us. Would absolutely consider going back "
The price is SAR 2,170
SAR 3,447 total
includes taxes & fees
31 Dec - 1 January 2025
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

Upstairs on Main

9.2 out of 10, Wonderful, (31)
"Check in was easy, beds are comfortable. I’m a big and tall guy, so only qualm I had was the small toilet, and low shower head. Aside from those, great stay!"
Upstairs on Main

Main Street Delight 1bedroom

10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (63)
"The bathroom was less than tidy and when I recall it was like that last time. Bathroom rug is dirty or just dirty looking. I advise property Meg to buy several Along with a Terry bath mat so you can cover it when using. No little extras like soap/shampoo are offered. I had My own. Overall the apartment is very cute would stay again. "
Heart of Lenox!! - renovated downtown apartment

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

10.0 out of 10, Exceptional, (22)
"We loved our stay. The rental was as described. Jiminy Peak is great and everything is within walking distance. We had a great time !!!"
The price is SAR 710
SAR 1,254 total
includes taxes & fees
21 Dec - 22 Dec
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

9.6 out of 10, Exceptional, (23)
"We were treated with such kindness and understanding of our situation. We would gladly recommend Alisha to anyone wanting to stay at their property. In fact, we are going back in May. "
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

10.0 out of 10, Exceptional, (2)
"Stayed one night at one of my favorite ski spots. Will be back again!"
The price is SAR 669
SAR 1,201 total
includes taxes & fees
23 Dec - 24 Dec
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (21)
"Location, location, location. Great use of space in this nicely decorated, conveniently located apt. Steps away from restaurants and shopping. 7 minutes from Kripalu. Great communication from owner. Looking forward to next stay."
Renovated Downtown 1bedroom

Baldwin Hill Retreat Guest House

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property and neighborhood were gorgeous! Walkable roads with low speed limits and a nearby park were major bonuses. Plenty of food options nearby, and downtown Great Barrington is only a short drive away. The house was super clean, gorgeously furnished, and very cozy. The beds and linens were very good quality and I had an incredibly restful stay. I will certainly be renting this spot for my next trip to the area! "
Baldwin Hill Retreat Guest House

Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi

10.0 out of 10, Exceptional, (1)
"We had a delightful stay in this very recently updated apartment. I think we were the first renters. it was so new and meticulous. The location was perfect on the Main Street in Stockbridge and walkable to the restaurants and shops. It was spacious, comfortable and very well equipped. We enjoy visiting the Divine Mercy Shrine in Stockbridge & the town for its charming nostalgic homes & downtown area. We were also graced with a little snowfall over the Christmas decorated street that added to...
Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi

Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Was a great spot to enjoy Jiminy Peak!"
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

Garfield House Studio at 208

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
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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Other property types in Canaan

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is SAR 634
SAR 733 total
includes taxes & fees
19 Dec - 20 Dec
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is SAR 710
SAR 779 total
includes taxes & fees
19 Dec - 20 Dec
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is SAR 488
SAR 527 total
includes taxes & fees
1 Jan - 2 January 2025
Micosta Leisure Inn
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.

Frequently asked questions

What's it like to stay at an apartment in Canaan?
You’ll find a lot of options for your stay in Canaan with 21 hotels and other accommodations. Though there aren’t many apartments, we can help you search for accommodations that are similar. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment such as a kitchen. You can also filter by similar property types like condos, vacation homes, or cottages.
Why consider an apartment versus a traditional hotel?
Often more spacious than a traditional hotel room, an apartment comes equipped with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home but also for couples looking for something with a more local feel.
What's the best apartment for my stay in Canaan?
Below are some of the top apartments in the area to choose from: Cozy Rustic Apt in 18th c Berkshire Farmhouse: Situated in Lanesborough, 14 mi/22.5 km from the heart of Canaan. Includes fireplaces and sofa beds. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 12.3 mi/19.8 km away in Lee. Private patios and fireplaces are included. Charming Apt in 18th c Berkshire Farmhouse: It’s situated in Lanesborough, 14 mi/22.5 km away. Includes fireplaces. New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.: 4.8 mi/7.7 km away in Richmond. Garfield House Studio at 208: It’s located in Lee, 12.3 mi/19.8 km from Canaan. Includes private patios.
What will the weather be like during my trip to Canaan?
Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Canaan. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What should I see in Canaan?
Queechy Lake and Hollow FIelds Reserve are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Hand Hollow State Forest and Bates Memorial State Park.
What's the best way to get to and around Canaan?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 8 mi (12.9 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 15.8 mi (25.4 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.