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Our top choices for The Berkshires vacation homes

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26 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 ¥23,064
¥39,546 total
includes taxes & fees
Jan 26 - Jan 27
Home in Great Barrington

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is ¥33,853
¥54,777 total
includes taxes & fees
Feb 16 - Feb 17
3-bedroom house in beautiful Berkshires, close to amenities!

Florida Mountain Log Cabin

Florida Mountain Log Cabin
2.0 star property
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is ¥29,067
¥53,792 total
includes taxes & fees
Jan 22 - Jan 23
Florida Mountain Log Cabin

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
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is ¥25,342
¥59,935 total
includes taxes & fees
Jan 25 - Jan 26
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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 ¥54,576
¥103,722 total
includes taxes & fees
Feb 12 - Feb 13
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥32,033
¥47,090 total
includes taxes & fees
Jan 26 - Jan 27
Family Ski Getaway in the Berkshires

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 ¥28,474
¥72,799 total
includes taxes & fees
Jan 26 - Jan 27
Sun Filled Lenox Retreat - Minutes to Tanglewood!

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 ¥21,356
¥42,408 total
includes taxes & fees
Feb 1 - Feb 2
Sweet Cozy Victorian in Housatonic. Close to everything.

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 ¥47,299
¥102,838 total
includes taxes & fees
Jan 22 - Jan 23
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
The price is ¥37,372
¥64,389 total
includes taxes & fees
Feb 17 - Feb 18
The Greylock Cabin

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!
2.0 star property
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 ¥42,569
¥78,119 total
includes taxes & fees
Jan 22 - Jan 23
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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 ¥50,937
¥115,879 total
includes taxes & fees
Jan 22 - Jan 23
Comfortable Berkshires retreat on mtn resort, SISO

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 ¥49,039
¥87,289 total
includes taxes & fees
Jan 25 - Jan 26
Great Barrington Get Away

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 ¥89,551
¥210,112 total
includes taxes & fees
Jan 22 - Jan 23
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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 ¥63,276
¥104,782 total
includes taxes & fees
Feb 8 - Feb 9
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16 reviews)
"Great place for a family reunion. Lots of bedrooms and bathrooms. Kitchen is large & well equipped"
United States
Veronica and Mark W.
The price is ¥99,494
¥181,758 total
includes taxes & fees
Jan 27 - Jan 28
Hancock Village Inn Near Jiminy Peak

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is ¥75,140
¥136,235 total
includes taxes & fees
Feb 12 - Feb 13
Spacious 5-bedroom house in charming Lee with WiFi

The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (73 reviews)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is ¥28,474
¥43,822 total
includes taxes & fees
Jan 26 - Jan 27
The Creation Station is a cozy place so make yourself at home.

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (47 reviews)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is ¥18,366
¥31,825 total
includes taxes & fees
Jan 23 - Jan 24
Lovely 2nd Floor Apartment

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (101 reviews)
"Beautiful, serene location with great penned in area for my lovable, niece pup! Spacious house with all the key amenities. Easy access for my elederly mom. "
United States
Lynn F.
The price is ¥18,366
¥49,006 total
includes taxes & fees
Jan 25 - Jan 26
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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 The Berkshires Hotel Reviews

Find out more about The Berkshires

The Berkshires Vacation Homes information

Number of reviews
439
Accommodation
327 Vacation Homes
Lowest Price
¥31,825
Highest Price
¥210,112

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