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Areas near Lenox

Travelers going to Lenox are booking October dates now. Secure your vacation rental today and have the perfect trip.

Great rentals within 20 miles that match your search

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 10

Comfortable Farmhouse in the Berkshires

  • 5
  • 12
  • Min stay varies

$326

Details

1 / 14

Modern Cozy Wooded Retreat

  • 2
  • 6
  • 30 nights min

$134

Details

1 / 12

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

  • 1
  • 4
  • 3 nights min

$201

Details

1 / 7

the BIG room at chestnut lodge

  • 1
  • 6
  • 2 nights min

$201

Details

1 / 32

Escape to the Berkshires!

  • 4
  • 8
  • 2 nights min

$275

Details

1 / 19

Restored Horse Barn On 13 Acres With Private Pond

  • 4
  • 10
  • 4 nights min

Inquire for Rates

Details

1 / 12

Fabulous Post & Beam Berkshire Rental

  • 7
  • 21 nights min

$180

Details

1 / 21

Serene Lakefront Cottage

  • 2
  • 4
  • Min stay varies

$150

Details

1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$326

Details

1 / 10

Country Victorian Serenity in the Berkshires

  • 4
  • 6
  • 7 nights min

$229

Details

1 / 6

Berkshires on the Pond

  • 2
  • 2
  • 4 nights min

$125

Details

1 / 13

Berkshires: Romantic Cottage with spectacular view

  • 1
  • 3
  • Min stay varies

$226

Details

1 / 16

Berkshires House, 40 wooded acres, Lake Frontage

  • 3
  • 8
  • 1 night min

$176

Details

1 / 21

Wyndham Bentley Brook at Jiminy Peak

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 18

Spacious wooded home

  • 4
  • 12
  • 3 nights min

$196

Details

1 / 11

Stockbridge Bowl house

  • 3
  • 8
  • 2 nights min

$226

Details

1 / 13

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

  • 2
  • 7
  • Min stay varies

$219

Details

1 / 8

Writer's Room at Chestnut Lodge

  • 1
  • 2
  • 2 nights min

$201

Details

1 / 14

Christmas in The Berkshires

  • 1
  • 4
  • 2 nights min

$176

Details

1 / 32

RIVERSONG "PENTHOUSE"

  • 1
  • 2
  • 1 night min

$129

Details

1 / 24

Berkshires Waterfront Lakehouse Sanctuary

  • 3
  • 6
  • 2 nights min

$196

Details

1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1 / 31

Beautifully decorated & immaculate log chalet

  • 3
  • 6
  • 2 nights min

$176

Details

1 / 19

Lake House in the Berkshires

  • 3
  • 8
  • 1 night min

$376

Details

1 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$231

Details

1 / 31

Big Beautiful 7 bedroom 3 bath hot tub pool table

  • 7
  • 18
  • 2 nights min

$300

Details

1 / 24

Beautiful Lakefront Berkshire Rental

  • 5
  • 6
  • 7 nights min

$351

Details

1 / 21

Gartner House, a charming home in Lenox

  • 4
  • 7
  • 2 nights min

$201

Details

1 / 30

INTERIOR DESIGNERS BOTANICAL GARDENS

  • 1
  • 5
  • Min stay varies

$150

Details

1 / 16

Luxury Fox Hollow Laurel Lake Ranch

  • 4
  • 11
  • Min stay varies

$501

Details

1 / 23

Charming spacious country home with stunning views

  • 5
  • 14
  • 3 nights min

$1001

Details

1 / 12

Heart of the Berkshires!

  • 3
  • 6
  • 2 nights min

$226

Details

1 / 8

Spacious Newly Renovated 2 BR Cono walk to town

  • 2
  • 6
  • 30 nights min

$100

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 25

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

  • 5
  • 14
  • 2 nights min

$450

Details

1 / 10

Heart of Lenox

  • 2
  • 4
  • Min stay varies

$176

Details

1 / 23

Renovated 2 bedroom in Heart of Lenox

  • 2
  • 4
  • Min stay varies

$300

Details

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