Vacation Homes in Berkshire County

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Check prices for these dates

Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov
In one month
5 Dec - 7 Dec
In two months
2 Jan - 4 Jan

Featured Vacation Homes in Berkshire County

Games room
Pet Friendly Riverfront Home in Great Barrington
Pet Friendly Riverfront Home in Great Barrington
8.8 out of 10, Excellent, (3)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,573
HK$2,313 total
includes taxes & fees
4 Nov - 5 Nov
Pet Friendly Riverfront Home in Great Barrington
Fridge, microwave, oven, stovetop
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
10.0 out of 10, Exceptional, (40)
"Our stay exceeded our expectations.The home is beautiful, cozy, very well maintained, appointed and located. We felt relaxed from the moment we walked in the door. We will definitely be back!"
United States
Courtney S.
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (132)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.
Amore Estate - beautiful room with many places to explore and relax in.
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.
Dining
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
9.6 out of 10, Exceptional, (16)
"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"
United States
Annie C.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Fridge, microwave, oven, stovetop
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
10.0 out of 10, Exceptional, (55)
"We were taking our first family ski trip and were lucky to stay at this great house which is only 10 minutes from Butternut. Super convenient, very comfortable and the huge kitchen was a perfect place for our family to gather after a day on the slopes. We loved it and would happily return next year!"
United States
Erin R.
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Exterior
Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape
Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape
7.4 out of 10, Good, (3)
"Beautiful quiet escape. Host was very prompt with answers to questions I had. Very nice re-model. I will definitely be back. "
United States
Christopher W.
Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape
Property grounds
Stay Lakeside This Summer!
Stay Lakeside This Summer!
9.8 out of 10, Exceptional, (79)
"Beautiful lake views, comfy and cozy house! We had a wonderful time. Thank you for sharing your home with us. "
United States
Anne-Marie A.
Stay Lakeside This Summer!
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is HK$3,302
HK$6,145 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Interior
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (227)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
United States
Anika J.
Peace and quiet on the lake
Smart TV, fireplace, DVD player, books
Contemporary Berkshire Home with Views of Taconic Golf Course
Contemporary Berkshire Home with Views of Taconic Golf Course
10.0 out of 10, Exceptional, (11)
"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."
United States
MARK S.
Contemporary Berkshire Home with Views of Taconic Golf Course
Property grounds
Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
10.0 out of 10, Exceptional, (25)
"We had another great weekend stay with friends! Can’t say enough good things about the house and property and location"
United States
Robin M.
Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
Exterior detail
Hearts Desire is a furnished whole house in a small, colorful garden center.
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (97)
"This was our third time at this property. We still love it and look forward to returning again."
United States
Lisa P.
Hearts Desire is a furnished whole house in a small, colorful garden center.
Interior
Secluded 4 bedroom home with sweeping mountain views in Williamstown
Secluded 4 bedroom home with sweeping mountain views in Williamstown
9.6 out of 10, Exceptional, (5)
Secluded 4 bedroom home with sweeping mountain views in Williamstown
Exterior
General Williams Estate House Lenox/Stockbridge
General Williams Estate House Lenox/Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (110)
"This was a great place to house our family of 12 during the weekend of our daughter’s wedding. There was plenty of space for everyone to gather. The beds were comfortable and all the bedrooms upstairs had their own bathroom - so nice! The house made our weekend extra special. Definitely recommend!"
United States
Fern L.
General Williams Estate House Lenox/Stockbridge
Exterior
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Woodland 5-BR Retreat 5-Min to Jiminy Peak
10.0 out of 10, Exceptional, (12)
"The house was beautiful, very clean and well kept."
United States
Erica G.
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Fridge, microwave, oven, stovetop
Modern Victorian Walk to Main Street
Modern Victorian Walk to Main Street
10.0 out of 10, Exceptional, (25)
"The house was perfect for our long weekend in Great Barrington. It’s very comfortable, clean, and well taken care of. The location is perfect. We loved being able to walk right into town. Highly recommend! "
United States
Catherine L.
Modern Victorian Walk to Main Street
Exterior
Sophisticated Lenox Retreat by Evergreen Home
Sophisticated Lenox Retreat by Evergreen Home
9.8 out of 10, Exceptional, (9)
"Well laid out, and great set-up for our family stay in Lenox for a wedding. All the amenities we needed, and back deck was comfortable for some down time. Highly recommended."
United States
Paul B.
Sophisticated Lenox Retreat by Evergreen Home
Fridge, microwave, oven, stovetop
Country Living just minutes from Everything!
Country Living just minutes from Everything!
10.0 out of 10, Exceptional, (29)
"Jandie's was the absolute best rental house we have ever stayed at. The house was clean and well kept, everything felt brand new. The set up was great, open kitchen, dining room and living room and made entertaining very easy. The kids had their own room and enjoyed spending time together in their own space. Julie was a pleasure to work with and accommodated us in anyway she could, from beginning to end. She even made us homemade delicious treats. We would highly recommend Jandie's and we...
United States
Michelle D.
Country Living just minutes from Everything!
Lake
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
9.4 out of 10, Exceptional, (62)
"We had a wonderful stay. The house was well appointed and comfortable for hanging out."
United States
Mallory V.
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
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 Berkshire County Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"I had a smooth check in. A little later I went back to the front desk to get an extra key, was asked my room number and last name. The associate, knew that I had asked for extra pillows when I made the reservation. I don't think he was even on my reservation on the computer yet to see the note. Asked if I had the extra pillows in the room and were they ok! Often hotels don't even notice this request, never mind remember it or ask about it. Great attention to details!"
Jenine 2-night trip
Posted 22 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Berkshire County

Berkshire County Vacation Homes information

Number of reviews
820
Accommodation
337 Vacation Homes
Lowest Price
HK$2,313
Highest Price
HK$6,145