Pittsfield Villas, Vacation Rentals & more


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Areas near Pittsfield

1 / 20

Berkshire's Getaway ---Peace & Tranquility

  • 3
  • 8
  • 2 nights min

$149

Details

Great rentals within 20 miles that match your search

1 / 10

Great Vacation House in the Berkshires on Richmond Pond

  • 2
  • 6
  • 7 nights min

$171

Details

1 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$229

Details

1 / 25

Luxury and Amenities in a Stunning Rustic Setting

  • 4
  • 14
  • Min stay varies

$355

Details

1 / 4

The Meadow House 4 bdrm 4 bath house

  • 4
  • 12
  • 2 nights min

$626

Details

1 / 12

little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!

  • 1
  • 4
  • 3 nights min

$199

Details

1 / 35

Stockbridge Country Inn

  • 8
  • 17
  • 3 nights min

$963

Details

1 / 23

Apartment walking distance to Mass MoCa!!

  • 2
  • 10
  • Min stay varies

$154

Details

1 / 8

Spacious Newly Renovated 2 BR Cono walk to town

  • 2
  • 6
  • 30 nights min

$100

Details

1 / 27

Shaker Hill

  • 5
  • 10
  • 3 nights min

$472

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$149

Details

1 / 7

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

  • 2
  • 6
  • 7 nights min

$156

Details

1 / 8

Writer's Room at Chestnut Lodge

  • 1
  • 2
  • 2 nights min

$199

Details

1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$298

Details

1 / 14

Modern Cozy Wooded Retreat

  • 2
  • 6
  • 30 nights min

$132

Details

1 / 10

Romantic Berkshire Cottage on Storybook Estate

  • 1
  • 2
  • 2 nights min

$224

Details

1 / 17

One of the Finest Homes and Best location in the Berkshires

  • 4
  • 10
  • 3 nights min

$497

Details

1 / 33

Wyndham Bentley Brook Resort

  • 2
  • 8
  • 3 nights min

$60

Details

1 / 13

Lakefront Berkshires Ski/Summer House, Great Views

  • 4
  • 10
  • 2 nights min

$187

Details

1 / 16

Family-friendly Cottage Near Lake, Tanglewood

  • 3
  • 7
  • Min stay varies

$283

Details

1 / 2

chestnut lodge Queens Room

  • 1
  • 2
  • 2 nights min

$174

Details

1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$134

Details

1 / 24

Perfect Getaway for Body, Mind and Soul

  • 3
  • 5
  • 7 nights min

$235

Details

1 / 25

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

  • 5
  • 14
  • 2 nights min

$447

Details

1 / 6

Jiminy Peak Ski Resort-Country Village's Best Unit

  • 2
  • 6
  • 1 night min

$249

Details

1 / 10

Berkshire House Share-The Blue Room

  • 3
  • 2
  • 1 night min

$75

Details

1 / 29

Beauty in the Berkshires

  • 6
  • 14
  • 3 nights min

$1687

Details

1 / 4

Iris Room

  • 1
  • 2
  • 1 night min

$149

Details

1 / 9

Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

  • 1
  • 4
  • 2 nights min

$249

Details

1 / 20

Enjoy Summer in The Berkshires. last minute July and Aug dates . Great Location

  • 3
  • 8
  • Min stay varies

$273

Details

1 / 9

Bentley Brook 2 bedroom 2 bathroom

  • 2
  • 8
  • 2 nights min

$66

Details

1 / 18

Mountain Views Atop Blueberry Hill on 40 Acres

  • 3
  • 6
  • 2 nights min

$199

Details

1 / 7

ROOM walking distance to Mass MoCa

  • 1
  • 2
  • 1 night min

$70

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$149

Details

1 / 12

The Smith Farm Homestead

  • 1
  • 2
  • 2 nights min

$144

Details

1 / 6

Retreat in the Woods

  • 2
  • 4
  • 2 nights min

$199

Details

1 / 5

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

  • 1
  • 4
  • 7 nights min

$156

Details

1 / 31

Big Beautiful 7 bedroom 3 bath hot tub pool table

  • 7
  • 18
  • 2 nights min

$298

Details

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