Pittsfield Villas, Vacation Rentals & More


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Areas near Pittsfield

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1 / 20

Berkshire's Getaway ---Peace & Tranquility

  • 3
  • 8
  • 2 nights min

$150

Details

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1 / 5

Berkshire Mountain Lodge - Fri, Sat,Sun check ins only! Inbox x

  • 1
  • 4
  • 7 nights min

$158

Details

1 / 31

Big Beautiful 7 bedroom 3 bath hot tub pool table

  • 7
  • 18
  • 2 nights min

$300

Details

Great rentals within 30 miles that match your search

1 / 30

INTERIOR DESIGNERS BOTANICAL GARDENS

  • 1
  • 5
  • Min stay varies

$150

Details

1 / 14

Perfect for skiers in the Berkshires

  • 3
  • 6
  • Min stay varies

$100

Details

1 / 25

Berkshires Waterfront Lakehouse Sanctuary

  • 3
  • 6
  • 2 nights min

$195

Details

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1 / 10

Great Vacation House in the Berkshires on Richmond Pond

  • 2
  • 6
  • 7 nights min

$172

Details

8
1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1 / 18

Historic Home on 8.5 Acres

  • 3
  • 9
  • 3 nights min

$400

Details

15
1 / 10

Stone School Cottage

  • 2
  • 5
  • 2 nights min

$155

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$150

Details

1
1 / 10

Heart of Lenox

  • 2
  • 4
  • Min stay varies

$175

Details

1 / 23

Renovated 2 bedroom in Heart of Lenox

  • 2
  • 4
  • Min stay varies

$300

Details

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Gartner House, a charming home in Lenox

  • 4
  • 7
  • 2 nights min

$200

Details

1 / 8

Spacious Newly Renovated 2 BR Cono walk to town

  • 2
  • 6
  • Min stay varies

$200

Details

1 / 13

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

  • 2
  • 7
  • Min stay varies

$219

Details

1 / 13

Jiminy Peak Luxury Ski In/Ski Out Home

  • 3
  • 8
  • Min stay varies

$329

Details

1 / 13

Berkshires Summer Rental Beaver Pond Hancock MA

  • 3
  • 6
  • 30 nights min

$250

Details

2
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Berkshires Vacation Rental - Bentley Brook Resort Suite

  • 2
  • 6
  • 3 nights min

$200

Details

1 / 23

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

  • 2
  • 6
  • 2 nights min

$200

Details

1
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Wyndham Bentley Brook - Fri-Fri, Sat-Sat, Sun-Sun only!

  • 2
  • 6
  • 7 nights min

$258

Details

3
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Wyndham Bentley Brook

  • 2
  • 8
  • 2 nights min

$200

Details

1 / 6

Jiminy Peak Ski Resort-Country Village's Best Unit

  • 2
  • 6
  • 1 night min

$250

Details

1 / 26

Dazzling 2BR Hancock Condo W/Private Deck, Charcoal Grill & Gorgeous Mountain

  • 2
  • 6
  • Min stay varies

$185

Details

1 / 9

Bentley Brook 2 bedroom 2 bathroom

  • 2
  • 8
  • 2 nights min

$66

Details

9
1 / 21

Wyndham Bentley Brook at Jiminy Peak

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 19

Charming Berkshires lakefront house, great views

  • 2
  • 5
  • 2 nights min

$200

Details

1 / 6

Thanksgiving week lux condo/4 Berkshires

  • 2
  • 4
  • 7 nights min

$229

Details

3
1 / 14

2200sf Country House on 16 Acres-2 Miles to Jiminy

  • 4
  • 9
  • 2 nights min

$225

Details

1 / 23

Charming spacious country home with stunning views

  • 5
  • 14
  • 3 nights min

$1000

Details

1 / 24

Vacation Village in the Berkshires

  • 2
  • 8
  • 7 nights min

$129

Details

1 / 10

Vacation Village in the Berkshires Available July 22-29

  • 2
  • 8
  • 7 nights min

$158

Details

1 / 14

Christmas in The Berkshires

  • 1
  • 4
  • 2 nights min

$175

Details

1 / 7

Vacation Village in the Berkshires - Fri-Fri, Sat-Sat, Sun-Sun only!

  • 2
  • 6
  • 7 nights min

$157

Details

2
1 / 16

PanoramicView1000 sq ft Guest Quarters Berkshires

  • 1
  • 6
  • 2 nights min

$145

Details

1 / 4

The Meadow House 4 bdrm 4 bath house

  • 4
  • 12
  • 2 nights min

$600

Details

1 / 17

Whitman Woods: Private Berkshire Vacation, 4 acre

  • 4
  • 8
  • 1 night min

$100

Details

1 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$200

Details

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