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Compare 86 Apartments in Canaan with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (13)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

10.0 out of 10, Exceptional, (1)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
The price is AED 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

10.0 out of 10, Exceptional, (5)
"Condo was conveniently located at the base of the mountain. Had everything you would need for a quick weekend getaway. Owner was available for any questions."
The price is AED 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

10.0 out of 10, Exceptional, (4)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
The price is AED 577
AED 1,091 total
includes taxes & fees
24 Feb - 25 Feb
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect location. Walking distance. Brand new apartment. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

9.6 out of 10, Exceptional, (30)
"Perfect 1 bedroom, ski in ski off , updated unit with great amenities! Owner super responsive and accommodating. Will definitely be back "
The price is AED 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (7)
"This is the second year we had our girls weekend at the Penthouse and it did not disappoint. The place is updated, very clean, and in a great location! Only suggestion would to get a nice big sectional couch! We had 8 people and not enough comfy seating. But beautiful apartment!! "
The Penthouse, Downtown Lenox by Evergreen Home

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

2.0 star property
9.4 out of 10, Exceptional, (3)
"Great stay "
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

10.0 out of 10, Exceptional, (1)
"Lovely quiet spot with plenty of eating options around the area. Well maintained."
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (24)
"My family had a great ski weekend at Howard’s place. Everything was as described and the location could not be beat! Howard was an excellent host - super communicative and very prompt in responding to the few questions we had. We would absolutely stay here again. "
The price is AED 768
AED 1,422 total
includes taxes & fees
25 Feb - 26 Feb
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

All comforts of home

9.8 out of 10, Exceptional, (37)
"Absolutely beautiful, cozy, and quiet. Highly recommend and look forward to staying again in the future. "
The price is AED 400
AED 506 total
includes taxes & fees
23 Feb - 24 Feb
All comforts of home

Modern Copake Falls Getaway

9.6 out of 10, Exceptional, (31)
"Cozy modern apartment with great views. Very close to Catamount and a short drive to Great Barrington. Michael was a great host."
Modern Copake Falls Getaway

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

9.8 out of 10, Exceptional, (17)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
The price is AED 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

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 AED 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

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

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (22)
"We’ve always had a great experience with Downtown Upstairs in Lenox and this was no exception. Easy access to the downtown stores and restaurants with the comfort of a nice, clean, well furnished apartment. "
Renovated Downtown 1bedroom

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

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

9.4 out of 10, Exceptional, (60)
"The property was fine for our purposes of visiting family. If we needed to cook, it would have been quite difficult, though not totally impossible. The furniture was comfortable and the rooms, except the kitchen, had plenty of space. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lovely bright apartment in pastoral shaker barn

10.0 out of 10, Exceptional, (2)
"We traveled from Arizona for a class reunion and stayed in apartment. The property was clean and well appointed. We were able to host a dinner with four family members we had not seen in years! Another highlight was sitting outside by the fire pit in the evening. The property host, Michelle, provided excellent check in instructions and answered any questions very promptly. This property worked out very well for us, but if you have an issue with stairs you might want to check out the other...
Lovely bright apartment in pastoral shaker barn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

9.0 out of 10, Wonderful, (10)
"Such a awesome facility! Love the room, the Jiminy property is very cool and you don’t even need to leave to go anywhere else because there is so much to do here. Stay."
The price is AED 577
AED 1,091 total
includes taxes & fees
24 Feb - 25 Feb
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous 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.
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Other property types in Canaan

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1765)
"Great place for a family vacation. Property very clean, quiet, and well organized "
The price is AED 400
AED 476 total
includes taxes & fees
3 Mar - 4 Mar
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is AED 438
AED 489 total
includes taxes & fees
23 Feb - 24 Feb
The Ponds at Foxhollow

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 694
AED 762 total
includes taxes & fees
23 Feb - 24 Feb
Jiminy Peak Mountain Resort
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 22 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: 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor: Located in Hancock, 12.7 mi/20.5 km from the heart of Canaan. Includes sofa beds. A fitness center and an indoor pool are on site. Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located 15.6 mi/25 km away in Great Barrington. Free WiFi, separate dining areas, and Smart TVs are included. 1500 sqft private entrance with beautiful views of the Berkshire Mountains: It’s situated in Lee, 13 mi/21 km away. Includes free WiFi, private patios, and Smart TVs. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: 12.3 mi/19.8 km away in Lee. Private patios and fireplaces are included. New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.: It’s situated in Richmond, 4.8 mi/7.7 km from Canaan.
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.