Berkshire County Vacation Rentals | Book Now, Save Up to 30%

All in pricing: Taxes and fees included

Save $165

Unit 1 of 6

Apartment in Hancock, MA

Nov 19 - 22

$149/night

4.8

15

1 bedroom

4 guests

$660$495total

Save $154

Preferred host

House in Sheffield, MA

Nov 22 - 25

$347/night

5.0

3

4 bedrooms

10 guests

$1,305$1,152total

Save $219

Preferred host

House in Sheffield, MA

Nov 19 - 22

$308/night

4.8

33

5 bedrooms

10 guests

$1,242$1,023total

Save $174

Preferred host

House in Stockbridge, VT

Nov 29 - Dec 2

$435/night

5.0

7

4 bedrooms

8 guests

$1,617$1,443total

Save $189

Preferred host

House in New Marlborough, MA

Nov 19 - 22

$295/night

4.8

34

3 bedrooms

6 guests

$1,195$1,006total

Save $101

Entire cabin in Stephentown, NY

Nov 23 - 26

$133/night

4.6

61

2 bedrooms

4 guests

$540$439total

Save $386

Whimstay gem

House in Hillsdale, NY

Nov 22 - 25

$525/night

4.9

52

4 bedrooms

8 guests

$2,131$1,745total

Save $215

Preferred host

House in Stockbridge, MA

Dec 28 - 31

$744/night

4.9

10

3 bedrooms

6 guests

$2,685$2,470total

Save $254

Whimstay gem

House in Great Barrington, MA

Nov 19 - 22

$464/night

4.9

66

3 bedrooms

6 guests

$1,836$1,582total

Save $1,021

Preferred host

House in Austerlitz, NY

Nov 19 - 22

$811/night

4.8

62

4 bedrooms

12 guests

$3,722$2,701total

Save $630

Preferred host

House in East Chatham, NY

Nov 27 - Dec 1

$882/night

4.9

16

4 bedrooms

8 guests

$4,544$3,914total

Save $489

Whimstay gem

House in Hillsdale, NY

Nov 30 - Dec 4

$804/night

4.9

34

4 bedrooms

8 guests

$4,058$3,569total

Save $116

Preferred host

House in New Marlborough, MA

Nov 19 - 22

$392/night

4.6

14

4 bedrooms

8 guests

$1,453$1,337total

Save $219

Preferred host

House in Great Barrington, MA

Nov 22 - 25

$293/night

4.7

68

4 bedrooms

12 guests

$1,206$987total

Save $284

Whimstay gem

House in Egremont, MA

Nov 22 - 25

$446/night

4.9

39

4 bedrooms

8 guests

$1,805$1,521total

Save $945

Whimstay gem

House in Monterey, MA

Dec 6 - 9

$743/night

4.9

61

4 bedrooms

12 guests

$3,330$2,385total

Save $105

House in Hancock, MA

Dec 4 - 7

$363/night

4.1

18

3 bedrooms

10 guests

$1,311$1,206total

Save $216

Preferred host

House in Great Barrington, MA

Nov 19 - 22

$369/night

5.0

4

3 bedrooms

8 guests

$1,442$1,226total

Save $281

Unit 1 of 2

Preferred host

House in West Stockbridge, MA

Nov 19 - 22

$948/night

5.0

11

6 bedrooms

11 guests

$3,514$3,233total

Save $212

Preferred host

House in Sheffield, MA

Dec 5 - 8

$628/night

5.0

10

4 bedrooms

14 guests

$2,297$2,085total

Save $62

Preferred host

Cabin in New Marlborough, MA

Nov 19 - 22

$211/night

5.0

9

1 bedroom

2 guests

$780$717total

Map shows last minute vacation rentals in Berkshire County