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Our top choices for The Berkshires vacation homes

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 ¥29,115
¥53,881 total
includes taxes & fees
Jan 20 - Jan 21
Florida Mountain Log Cabin

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ¥23,102
¥59,610 total
includes taxes & fees
Jan 21 - Jan 22
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

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 ¥23,211
¥39,798 total
includes taxes & fees
Jan 26 - Jan 27
Home in Great Barrington

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 ¥25,384
¥61,097 total
includes taxes & fees
Jan 22 - Jan 23
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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 ¥32,086
¥47,167 total
includes taxes & fees
Jan 20 - Jan 21
Family Ski Getaway in the Berkshires

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, (32 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 ¥47,377
¥103,007 total
includes taxes & fees
Jan 26 - Jan 27
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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 ¥21,391
¥38,407 total
includes taxes & fees
Feb 2 - Feb 3
Sweet Cozy Victorian in Housatonic. Close to everything.

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.4 out of 10, Exceptional, (3 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 ¥28,521
¥72,919 total
includes taxes & fees
Jan 19 - Jan 20
Sun Filled Lenox Retreat - Minutes to Tanglewood!

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 ¥37,434
¥64,329 total
includes taxes & fees
Feb 8 - Feb 9
The Greylock Cabin

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 ¥51,262
¥116,618 total
includes taxes & fees
Jan 20 - Jan 21
Comfortable Berkshires retreat on mtn resort, SISO

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 ¥84,217
¥141,905 total
includes taxes & fees
Feb 6 - Feb 7
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

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 ¥42,639
¥78,247 total
includes taxes & fees
Jan 19 - Jan 20
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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 ¥90,123
¥211,454 total
includes taxes & fees
Jan 19 - Jan 20
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
9.4 out of 10, Exceptional, (26 reviews)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is ¥49,120
¥87,964 total
includes taxes & fees
Jan 25 - Jan 26
Great Barrington Get Away

Catamount, Zip Line, Private Setting, Book Now!

Catamount, Zip Line, Private Setting, Book Now!
Egremont
10.0 out of 10, Exceptional, (7 reviews)
"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."
United States
Jason W.
The price is ¥75,105
¥182,962 total
includes taxes & fees
Jan 19 - Jan 20
Catamount, Zip Line, Private Setting, Book Now!

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (16 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ¥106,312
¥190,552 total
includes taxes & fees
Feb 2 - Feb 3
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 ¥75,264
¥136,459 total
includes taxes & fees
Feb 12 - Feb 13
Spacious 5-bedroom house in charming Lee with WiFi

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Monterey
10.0 out of 10, Exceptional, (1 review)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
The price is ¥134,366
¥274,201 total
includes taxes & fees
Jan 18 - Jan 19
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

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 ¥63,380
¥105,132 total
includes taxes & fees
Feb 10 - Feb 11
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (46 reviews)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
The price is ¥18,396
¥31,877 total
includes taxes & fees
Jan 20 - Jan 21
Lovely 2nd Floor Apartment
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
275
Accommodation
327 Vacation Homes
Lowest Price
¥31,877
Highest Price
¥274,201

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