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craigslist

Vacation Rentals in Western Massachusetts

  1. see also
  2. IRRESISTIBLE CONTEMPORARY FAMILY HOME W/MAGNIFICENT VIEWS
    $1
    23 Castle Ln, Great Barrington
  3. IRRESISTIBLE CONTEMPORARY FAMILY HOME W/MAGNIFICENT VIEWS
    $1
    23 Castle Ln, Great Barrington
  4. WATERFRONT COTTAGE SPRING GETAWAYS GREAT RATES
    $150
    East Matunuck
  5. Waterfront house, dock, deck, great lake views
    $1,350
    Great Barrington
  6. The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome
    $180
    whitingham, VT
  7. NC coast
    $1,400
    supply
  8. Berkshire vacation rental in Plainfield Massachusetts
    $249
    Plainfield, MA
  9. ►2026 Presidents Day Week - Luxury Ski Resort Condo at Jiminy Peak
    $1,750
    Hancock, The Berkshires, MA
  10. Cozy little Condo, Great for Snowbirds for travelling workers.
    $55
    Garden City SC
  11. $1,000 / 2 BR - Spacious
    $1,000
    Lenox
  12. Vacation Village in the Berkshires Sunday July 12-19 of 2026
    $1,495
    2-bedroom lockoff - 276 Brodie Mountain Rd - Hancock MA
  13. Vacation in a Berkshire Farmhouse
    $325
    WEST STOCKBRIDGE
  14. 2 BDR House for rent
    $1,800
    West Springfield