Monterey Vacation Rentals, Houses & More


1 - 38 of 117

View larger map

Areas near Monterey

Great rentals within 20 miles that match your search

1 / 21

The Playhouse: 7,000 Sq Feet of Berkshires Luxury

  • 6
  • 26
  • Min stay varies

$676

Details

1 / 11

Riverwood - Cozy Carriage House in the Woods

  • 1
  • 2
  • 2 nights min

$166

Details

1 / 10

Comfortable Farmhouse in the Berkshires

  • 5
  • 12
  • Min stay varies

$326

Details

1 / 21

Serene Lakefront Cottage

  • 2
  • 4
  • Min stay varies

$150

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 / 23

Renovated 2 bedroom in Heart of Lenox

  • 2
  • 4
  • Min stay varies

$300

Details

1 / 18

Spacious wooded home

  • 4
  • 12
  • 3 nights min

$196

Details

1 / 13

Short Walk to Lake, Peaceful Getaway, Scenic Views

  • 3
  • 6
  • 2 nights min

$171

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 11

Stockbridge Bowl house

  • 3
  • 8
  • 2 nights min

$226

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 18

Mountain Views Atop Blueberry Hill on 40 Acres

  • 3
  • 6
  • 2 nights min

$201

Details

1 / 11

Berkshires Spacious Comfortable Charming Farmhouse

  • 3
  • 8
  • 2 nights min

$300

Details

1 / 25

Berkshire Estate: Exquisitely furnished 6,700sf

  • 6
  • 12
  • 7 nights min

$644

Details

1 / 7

Deluxe New Home, 2 Master Suites, Tanglewood Area

  • 5
  • 12
  • 3 nights min

$750

Details

1 / 19

Restored Horse Barn On 13 Acres With Private Pond

  • 4
  • 10
  • 4 nights min

Inquire for Rates

Details

1 / 32

Escape to the Berkshires!

  • 4
  • 8
  • 2 nights min

$275

Details

1 / 23

Escape to Lakeville CT ** Lime Rock *August Dates available* Hotchkiss

  • 3
  • 6
  • Min stay varies

$351

Details

1 / 7

the BIG room at chestnut lodge

  • 1
  • 6
  • 2 nights min

$201

Details

1 / 19

Lake House in the Berkshires

  • 3
  • 8
  • 1 night min

$376

Details

1 / 31

Beautifully decorated & immaculate log chalet

  • 3
  • 6
  • 2 nights min

$176

Details

1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1 / 15

Outdoor getaway hunting,fishing,skiing..relaxation

  • 3
  • 9
  • 2 nights min

$191

Details

1 / 23

Charming spacious country home with stunning views

  • 5
  • 14
  • 3 nights min

$1001

Details

1 / 8

Cozy & Modern Home -mins from Tanglewood & Kripalu

  • 2
  • 6
  • 2 nights min

$125

Details

1 / 37

Charming 2+2 Lakeside Cottage on Best Lake in CT

  • 2
  • 4
  • Min stay varies

$181

Details

1 / 15

Newly Renovated Vacation Home near Catamount Ski

  • 3
  • 10
  • Min stay varies

$300

Details

1 / 32

RIVERSONG "PENTHOUSE"

  • 1
  • 2
  • 1 night min

$129

Details

1 / 8

Writer's Room at Chestnut Lodge

  • 1
  • 2
  • 2 nights min

$201

Details

1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$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 / 23

Spacious Lakeside Berkshire Home

  • 4
  • 10
  • Min stay varies

$401

Details

1 / 16

Berkshires House, 40 wooded acres, Lake Frontage

  • 3
  • 8
  • 1 night min

$176

Details

1 / 24

Beautiful Lakefront Berkshire Rental

  • 5
  • 6
  • 7 nights min

$351

Details

1 / 12

Fabulous Post & Beam Berkshire Rental

  • 7
  • 21 nights min

$180

Details

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more
See only the properties that can be booked online with Payment Protection.
Learn more