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Our top choices for Housatonic vacation homes

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is ¥21,225
¥42,148 total
includes taxes & fees
Feb 10 - Feb 11
Sweet Cozy Victorian in Housatonic. Close to everything.

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ¥16,980
¥51,417 total
includes taxes & fees
Feb 10 - Feb 11
Near Tanglewood: Historic Summer Retreat

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (11 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is ¥25,187
¥60,797 total
includes taxes & fees
Feb 11 - Feb 12
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
The price is ¥16,697
¥22,223 total
includes taxes & fees
Feb 10 - Feb 11
All the comforts of home

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

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is ¥47,009
¥102,207 total
includes taxes & fees
Feb 10 - Feb 11
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ¥26,036
¥43,308 total
includes taxes & fees
Feb 22 - Feb 23
Home in Great Barrington

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ¥37,261
¥77,797 total
includes taxes & fees
Mar 8 - Mar 9
Cheerful 3-bedroom cottage with woodstove

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (9 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥31,837
¥46,801 total
includes taxes & fees
Feb 10 - Feb 11
Family Ski Getaway in the Berkshires

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (72 reviews)
"Howie was a great host, very responsive and accommodating. If we find ourselves in the area in the future , will def try to stay here again "
United States
jon e.
The price is ¥49,839
¥97,642 total
includes taxes & fees
Feb 12 - Feb 13
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
8.0 out of 10, Very Good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is ¥27,514
¥87,872 total
includes taxes & fees
Feb 10 - Feb 11
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is ¥24,212
¥61,983 total
includes taxes & fees
Mar 2 - Mar 3
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is ¥44,808
¥82,363 total
includes taxes & fees
Mar 1 - Mar 2
Great Barrington Get Away

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is ¥28,300
¥72,353 total
includes taxes & fees
Feb 10 - Feb 11
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ¥53,455
¥92,373 total
includes taxes & fees
Feb 22 - Feb 23
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
9.0 out of 10, Wonderful, (7 reviews)
"Kind and responsive host."
United States
Javier
The price is ¥50,625
¥115,169 total
includes taxes & fees
Feb 12 - Feb 13
Comfortable Berkshires retreat on mtn resort, SISO

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is ¥52,669
¥98,609 total
includes taxes & fees
Feb 10 - Feb 11
Luxury Barn Retreat — All-Season Escape Awaits!

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ¥89,427
¥209,474 total
includes taxes & fees
Feb 22 - Feb 23
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ¥29,715
¥50,050 total
includes taxes & fees
Feb 17 - Feb 18
3-bedroom house in beautiful Berkshires, close to amenities!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is ¥42,308
¥77,640 total
includes taxes & fees
Feb 21 - Feb 22
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Becket
The price is ¥52,669
¥96,764 total
includes taxes & fees
Feb 10 - Feb 11
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
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 Housatonic Hotel Reviews

Find out more about Housatonic

Housatonic Vacation Homes information

Number of reviews
312
Accommodation
425 Vacation Homes
Lowest Price
¥22,223
Highest Price
¥209,474