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Compare 81 Apartments in Canaan with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Living area
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
Charming Apartment In Berkshire Victorian Home
Exterior
Charming Apartment In Berkshire Victorian Home
7.8 out of 10, Good, (7)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Beautiful State of Art Kitchen Awaits in this spacious 900 Sq FT Suite
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. "
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
The Brooks Motel: Exceptional Suite
The Brooks Motel: Exceptional Suite
10.0 out of 10, Exceptional, (2)
"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."
The price is AED 584
AED 708 total
includes taxes & fees
23 Nov - 24 Nov
The Brooks Motel: Exceptional Suite
Garfield House Studio at 208
Exterior
Garfield House Studio at 208
9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
Cozy Rustic Apt in 18th c Berkshire Farmhouse
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 AED 533
AED 797 total
includes taxes & fees
23 Nov - 24 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Private apartment in beautiful country barn
Living area
Private apartment in beautiful country barn
10.0 out of 10, Exceptional, (18)
"Great farmhouse in the Berkshires. Location is out of the way without being out of the way. Communications with the host is great. Very accommodating."
Private apartment in beautiful country barn
Lake house with wrap around porch&beautiful view, minutes from the NYS Capitol!
Property grounds
Lake house with wrap around porch&beautiful view, minutes from the NYS Capitol!
8.6 out of 10, Excellent, (8)
"Beautiful location and comfortable and clean. Would highly recommend. "
Lake house with wrap around porch&beautiful view, minutes from the NYS Capitol!
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
9.2 out of 10, Wonderful, (9)
"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 382
AED 828 total
includes taxes & fees
24 Nov - 25 Nov
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Main Street Delight 1bedroom
Living area
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
Private kitchen
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
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Comfortable Living Room with Pullout Queen Sofa Bed and Smart TV with Full DVD Library and Board Game library for those nights in.
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
9.6 out of 10, Exceptional, (29)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
The price is AED 382
AED 828 total
includes taxes & fees
24 Nov - 25 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
9.6 out of 10, Exceptional, (21)
"Nice little cabin on a beautiful piece of property. The dirt road leading to the house was very narrow and bumpy but looks like they were in the process of smoothing out the road. The cabin is very cute inside and clean. We had three people so inside there’s not a lot of seating but it’s a tiny house so there’s not a lot of space for them to add additional seating. Just something to keep in mind. They do allow dogs. Our dog really enjoyed swimming in the pond. Wish they’d had a hose to bath her...
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Fully Redone Suite with master King Bed
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 382
AED 828 total
includes taxes & fees
24 Nov - 25 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Baldwin Hill Retreat Guest House
Living area
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
Gateway to the Berkshires - Renovated downtown apartment
Room
Gateway to the Berkshires - Renovated downtown apartment
10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Exterior
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
2.0 star property
10.0 out of 10, Exceptional, (1)
"This location was perfect for hiking the AT. The trail is only a few feet from the front door. The backyard is very nice, and they had chairs and tables to sit out. The apartment was a nice size for two people. There was no tv, so we used our computer. The kitchen was great to have since we didn't plan on eating out every night. There are plenty of restaurants in the area. The hosts were great and very responsive. The fall colors made the trip extra special."
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Living area
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!
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior
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
Charming Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (30)
"Some friends and I were in town for a wedding and were just staying the night and the property was perfect for what we needed! It was very clean and well-maintained. The only minor thing was the building is close to the road and we could hear some traffic at night, but it wasn’t too disruptive. We really enjoyed our stay, thank you!"
The price is AED 533
AED 797 total
includes taxes & fees
23 Nov - 24 Nov
Charming Apt in 18th c Berkshire Farmhouse
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
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is AED 620
AED 717 total
includes taxes & fees
23 Nov - 24 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
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 AED 547
AED 600 total
includes taxes & fees
23 Nov - 24 Nov
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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?
Here are some of the more popular apartments in the area to choose from: New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.: Situated in Richmond, 4.8 mi/7.7 km from the heart of Canaan. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: It’s situated in Lee, 12.3 mi/19.8 km away. Includes private patios and fireplaces. Garfield House Studio at 208: 12.3 mi/19.8 km away in Lee. Cozy Rustic Apt in 18th c Berkshire Farmhouse: It’s located in Lanesborough, 14 mi/22.5 km from Canaan. Includes fireplaces and sofa beds.
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.