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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Vacation Homes in Canann Village Historic District

Stockbridge Village in Summer
Dining

Stockbridge Village in Summer

9.0 out of 10, Wonderful, (18)
"This is a great home within walking distance of the interesting town of Stockbridge. The place is well equipped and has a charm consistent of what you can expect for a historic farm house. We would stay here again."
Stockbridge Village in Summer
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Fridge, microwave, oven, stovetop

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

10.0 out of 10, Exceptional, (37)
"We had the most wonderful trip! The location is perfect - easy access to downtown GB but still very relaxing and private. The kitchen is beautifully equipped and we ended up cooking most of our meals there. And the living room/great room led to hours of conversation. Can't wait to come back for a longer stay."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Bluebird Valley Farmhouse
Property grounds

Bluebird Valley Farmhouse

10.0 out of 10, Exceptional, (69)
"We stayed at the property while attending a family wedding. The house and yard were perfect. The best Vrbo we’ve ever stayed at. Would stay there again!"
Bluebird Valley Farmhouse
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
The price is SAR 889
SAR 1,885 total
includes taxes & fees
13 Oct - 14 Oct
Cheerful 3-bedroom cottage with woodstove
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (25)
"We had a wonderful time in this home. It accommodated our family of 4 easily. Several of us had to work the first day there and there were ample quiet spots and quality wifi for us. So easy to walk to town to restaurants etc"
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Falls Reach In The Heart of Copake
Property grounds

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Interior

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (82)
"Great location and fully equipped cabin! I hope to return sometime soon Everything was perfect!"
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (21)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Whispering Estate Guest House - A Romantic Countryside Getaway
Exterior detail

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (3)
"Beautiful property and great location. A true retreat. "
The price is SAR 3,000
SAR 4,551 total
includes taxes & fees
5 Oct - 6 Oct
Whispering Estate Guest House - A Romantic Countryside 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, (31)
"Property was exactly as it appears and was perfect for our needs over a weekend celebrating a friends birthday nearby. Owner was very responsive to any questions. Would definitely recommend. "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
The Meadows House @ Otis Ridge w/ 7-person hot tub
Outdoor spa tub

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.6 out of 10, Exceptional, (37)
"We had a lovely time. Peaceful and cozy house, great private hot tub"
The Meadows House @ Otis Ridge w/ 7-person hot tub
A Grand property in Historic Stockbridge
Fridge, microwave, oven, stovetop

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (102)
"The Taggart House was a wonderful place to gather with friends and family to celebrate my birthday. The house is beautiful; the rooms are large; kitchen is great; bugs kept us from hanging out in the backyard but the conservatory was light and bright and a perfect spot for cocktails. We loved the proximity to the town of Stockbridge and we would walk back and forth a couple times a day. We had a couple of small issues, and Caitlin was very responsive in answering my questions/concerns. All in...
A Grand property in Historic Stockbridge
Lakefront Designer House in Pine Plains, NY.
Property grounds

Lakefront Designer House in Pine Plains, NY.

6.8 out of 10, (3)
"The interior of the house is comfortable, light and airy, with windows that look out on the lake. Exerior needs some work, washing machines underground, area could use some clean up. Lost running water for a day due to problem with pump, owner on it immediately. Location was terrific, about halfway between Rhinebeck and the Massachusetts border. Good walks in beautiful countryside."
Lakefront Designer House in Pine Plains, NY.
Hudson Valley and The Berkshires getaway
Interior

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (7)
"Place was decorated very nicely and it was very quiet and peaceful. "
Hudson Valley and The Berkshires getaway
Stockbridge Village Cottage With Mountain View’s and walk to town
Outdoor dining

Stockbridge Village Cottage With Mountain View’s and walk to town

9.8 out of 10, Exceptional, (63)
"Perfect long weekend with family at this lovely home!"
Stockbridge Village Cottage With Mountain View’s and walk to town
Spacious Home nestled along the Blackberry River in Northwest CT
Fridge, microwave, oven, stovetop

Spacious Home nestled along the Blackberry River in Northwest CT

10.0 out of 10, Exceptional, (86)
"House was great, lots of space and very clean, Had everything we needed. The host was terrific- We will definitely be staying again."
Spacious Home nestled along the Blackberry River in Northwest CT
Private Lakefront Home w/ Private Lake, 3 Bedrooms - Minutes to Hotchkiss
Interior

Private Lakefront Home w/ Private Lake, 3 Bedrooms - Minutes to Hotchkiss

2.0 star property
Private Lakefront Home w/ Private Lake, 3 Bedrooms - Minutes to Hotchkiss
Beautiful House in the Woods: Huge Yard, Hot Tub
Fridge, microwave, oven, stovetop

Beautiful House in the Woods: Huge Yard, Hot Tub

Beautiful House in the Woods: Huge Yard, Hot Tub
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 Canann Village Historic District Hotel Reviews

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"I was on a motorcycle riding trip. The Monument Mountain Motel was great ... located in a great part of Massachusetts for riding ... and was very clean and a very nice place."
Thomas 2-night trip
Posted 7 days ago
Monument Mountain Motel