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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 236 Vacation Homes in Canann Village Historic District with updated reviews, rates, and availability.

Remodeled Lakefront retreat!! Come join us for Ski Season!!
Aerial view

Remodeled Lakefront retreat!! Come join us for Ski Season!!

9.6 out of 10, Exceptional, (5)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
Remodeled Lakefront retreat!! Come join us for Ski Season!!
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (45)
"We had an amazing long ski weekend at the Great Escape Ski Cottage. The listing is very accurate. Great communication with Shay. The house was immaculate upon arrival. The layout of the house was perfect for our family (6 adults and 4 children aged 4-9). One beautiful Master Bedroom on the first floor. Two of the other equally beautiful bedrooms are on the second floor. The linens were hotel quality! The "Kid's Quarters" was located off of the kitchen/laundry room. A playroom with multiple games...
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.6 out of 10, Exceptional, (19)
"Our family had a wonderful experience and stay. "
The price is AED 790
AED 1,231 total
includes taxes & fees
19 Mar - 20 Mar
Home in Great Barrington
Mountain View Getaway
Outdoor dining

Mountain View Getaway

10.0 out of 10, Exceptional, (49)
"Such a magical place…always enjoy our stay. The home is so comfy - the hosts are amazing. "
Mountain View Getaway
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (25)
"Our family of 4 stayed here while skiing at Catamount - great proximity, exactly as pictured, clean, and perfect size. Host was responsive - would stay here again!"
The price is AED 621
AED 1,264 total
includes taxes & fees
13 Mar - 14 Mar
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Linden by AvantStay | Countryside Berkshire Escape
Interior

Linden by AvantStay | Countryside Berkshire Escape

9.6 out of 10, Exceptional, (9)
"Our family had a wonderful time staying at Linden House. It was comfortable for the 6 adults and 4 young children. We loved the sophisticated charm of the house with its beautiful artwork and furnishings. It has quality appliances and a fully equipped kitchen. We plan to return next year."
Linden by AvantStay | Countryside Berkshire Escape
Perfect Nature Retreat In Great Barrington
Exterior

Perfect Nature Retreat In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Retreat In Great Barrington
Monterey Home w/ Hot Tub, Pool & Game Room!
Outdoor spa tub

Monterey Home w/ Hot Tub, Pool & Game Room!

9.0 out of 10, Wonderful, (2)
"Beautiful property. Lovely grounds. Clean and so much fun for the little ones. Communication and service were excellent. "
Monterey Home w/ Hot Tub, Pool & Game Room!
Beautiful Berkshires Colonial on 7 acres
Game room

Beautiful Berkshires Colonial on 7 acres

10.0 out of 10, Exceptional, (5)
"Our family of 4 really enjoyed staying in this cozy, comfortable and beautifully-decorated farmhouse. Communication with the owners was easy and they had lots of great tips for enjoying the area, and the house had all of the essentials needed for a great weekend away. We’d intended to ski at nearby Catamount or Butternut but didn't manage to book lessons in time (lesson learned: book early for holiday weekends!), but Jiminy Peak was a great alternative an easy day trip further north. We’d...
Beautiful Berkshires Colonial on 7 acres
Secluded Family Home in Serene Stockbridge Woods
Fridge, microwave, oven, stovetop

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (20)
"Couldn't ask for anything better. A big living room to hang out together, open-plan with the kitchen. Perfectly comfortable!"
Secluded Family Home in Serene Stockbridge Woods
Charming Columbia County Farm House
Outdoor dining

Charming Columbia County Farm House

9.4 out of 10, Exceptional, (23)
"Our family had a wonderful time staying at this home. We played many games at the table and watched the fire burn in the stove. It was a cozy place with reading areas and the capability to get off screen time for the kids. "
Charming Columbia County Farm House
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Property grounds

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2.0 star property
8.8 out of 10, Excellent, (3)
"Property is lovely and very well maintained. We stayed for over 10 days and it was a perfect home away from home. Owners are very kind and accommodating — when I couldn’t find a hair dryer one was delivered to the house within a couple of hours. They also offered to relocate us if we were bothered by the nearby forest fire, which was not necessary. I hope we’ll have the opportunity to stay again."
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Lakeside Peninsula Escape
Outdoor dining

Lakeside Peninsula Escape

Lakeside Peninsula Escape
Private Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Private Estate, Heated Yearround Outdoor Pool

9.8 out of 10, Exceptional, (17)
"The home was beautiful and it was a gorgeous property too. It had all the right amenities in the kitchen. "
Private Estate, Heated Yearround Outdoor Pool
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (149)
"The location is beautiful and there are lots of places to visit in the area. The house is nice; great view of Otis Reservoir. It took us a while to figure out the multiple thermostats, but it was a good Christmas house. The owner was nice enough to allow us to have a Christmas tree, and had someone make an extra trash pick up for us after Christmas.The one thing we were disappointed in was the cleanliness. Shower curtains were moldy, some of the dishes weren't very clean, expired condiments...
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Antique Farmhouse Totally Restored
Exterior

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (86)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
A Grand property in Historic Stockbridge
Fridge, microwave, oven, stovetop

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (96)
"We had an amazing time. We had several out of town guests who stayed at the home and then a birthday party with local guests in the ballroom. The ballroom is absolutely stunning. The chef enjoyed the kitchen. There was plenty of parking and a beautiful setting. I would stay again. "
A Grand property in Historic Stockbridge
Minutes from downtown Great Barrington, Convenient location
Exterior

Minutes from downtown Great Barrington, Convenient location

10.0 out of 10, Exceptional, (47)
"We had a great time, lots of space and a perfect home base for catamount, great Barrington, etc. "
Minutes from downtown Great Barrington, Convenient location
Lakefront Winter Winderland in New England Just 2 Hours From NYC
Interior

Lakefront Winter Winderland in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (66)
"The host was great and the property had everything we wanted and more. We will be back."
Lakefront Winter Winderland in New England Just 2 Hours From NYC
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 Canann Village Historic District

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (14)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (45)
"We had an amazing long ski weekend at the Great Escape Ski Cottage. The listing is very accurate. Great communication with Shay. The house was immaculate upon arrival. The layout of the house was perfect for our family (6 adults and 4 children aged 4-9). One beautiful Master Bedroom on the first floor. Two of the other equally beautiful bedrooms are on the second floor. The linens were hotel quality! The "Kid's Quarters" was located off of the kitchen/laundry room. A playroom with multiple games...
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.