Monterey Vacation Rentals, Houses & More


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1 / 16

Berkshires House, 40 wooded acres, Lake Frontage

  • 3
  • 8
  • Min stay varies

$175

Details

1 / 23

Spacious Lakeside Berkshire Home

  • 4
  • 10
  • Min stay varies

$400

Details

1 / 24

Beautiful Lakefront Berkshire Rental

  • 5
  • 6
  • 7 nights min

$350

Details

Great rentals within 30 miles that match your search

1 / 25

Berkshire Estate: Exquisitely furnished 6,700sf

  • 6
  • 12
  • 7 nights min

$643

Details

1 / 27

Enchanted Cottage on Babbling Brook

  • 3
  • 6
  • Min stay varies

$250

Details

1 / 12

Fabulous Post & Beam Berkshire Rental

  • 7
  • 21 nights min

$179

Details

1
1 / 24

Lakefront 2BR Great Barrington Area Cottage w/Deck

  • 2
  • 4
  • Min stay varies

$185

Details

1 / 10

Country Victorian Serenity in the Berkshires

  • 4
  • 6
  • 7 nights min

$229

Details

1
1 / 15

Charming and Spacious Colonial Farmhouse on 4 Acre Estate

  • 4
  • 8
  • 2 nights min

$500

Details

1 / 8

Charming Room with Private Bath in Colonial Farmho

  • 1
  • 2
  • 2 nights min

$250

Details

1 / 9

Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

  • 1
  • 4
  • 2 nights min

$250

Details

1 / 10

Romantic Berkshire Cottage on Storybook Estate

  • 1
  • 2
  • 2 nights min

$225

Details

1 / 22

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

  • 6
  • 14
  • 7 nights min

$600

Details

1 / 12

July4th Berkshires/James Taylor/2Bed Presidential

  • 2
  • 6
  • 2 nights min

$375

Details

1 / 25

NEW! Charming 3BR Great Barrington House by River!

  • 3
  • 8
  • Min stay varies

$205

Details

1 / 7

Deluxe New Home, 2 Master Suites, Tanglewood Area

  • 5
  • 12
  • 3 nights min

$750

Details

1
1 / 12

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

  • 1
  • 4
  • 3 nights min

$200

Details

1 / 19

Restored Horse Barn On 13 Acres With Private Pond

  • 4
  • 10
  • 4 nights min

$1500

Details

1 / 13

Designer Loft Style Residence

  • 3
  • 6
  • 7 nights min

$450

Details

1 / 18

Restored 1940s Cabin 30 Mile Views

  • 2
  • 5
  • 2 nights min

$250

Details

1 / 6

Berkshires on the Pond

  • 2
  • 2
  • 4 nights min

$125

Details

2
1 / 27

Shaker Hill

  • 5
  • 10
  • 3 nights min

$475

Details

3
1 / 30

Gem of the Berkshires, walk to downtown & lake.

  • 5
  • 12
  • 2 nights min

$400

Details

2
1 / 24

Perfect Getaway for Body, Mind and Soul

  • 3
  • 5
  • 7 nights min

$236

Details

1 / 25

Luxury and Amenities in a Stunning Rustic Setting

  • 4
  • 14
  • Min stay varies

$500

Details

1
1 / 8

Writer's Room at Chestnut Lodge

  • 1
  • 2
  • 2 nights min

$200

Details

1 / 7

the BIG room at chestnut lodge

  • 1
  • 6
  • 2 nights min

$200

Details

1
1 / 2

chestnut lodge Queens Room

  • 1
  • 2
  • 2 nights min

$175

Details

2
1 / 47

Jacob's Tanglewood Ranch (great for groups 10+)

  • 5
  • 20
  • Min stay varies

$999

Details

5
1 / 32

Beautiful New Construction Vacation Home

  • 4
  • 12
  • Min stay varies

$499

Details

1
1 / 17

Restored 1886 Eyebrow Colonial

  • 2
  • 6
  • 7 nights min

$215

Details

4
1 / 10

Apple Cottage

  • 3
  • 8
  • 1 night min

$375

Details

1
1 / 10

Cozy and clean in Gt Barrington- 1 week in summer!

  • 2
  • 4
  • 3 nights min

$195

Details

1 / 24

1BR + Loft Lee House - Walk to Main Street!

  • 1
  • 9
  • Min stay varies

$165

Details

1 / 26

3BD Newly Rennovated Contempoary Near Stockbridge

  • 3
  • 6
  • 3 nights min

$300

Details

1
1 / 14

The perfect Southern Berkshire winter vacation esc

  • 4
  • 10
  • 7 nights min

$500

Details

1 / 24

Country Elegance in the Berkshires

  • 4
  • 12
  • 2 nights min

$650

Details

1
1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$300

Details

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