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craigslist

Vacation Rentals in Western Massachusetts

  1. see also
  2. August 2026 Berkshire Rental
    $12,550
    Lee, MA
  3. Waterfront house, dock, deck, great lake views
    $1,350
    Great Barrington
  4. Vacation in a Berkshire Farmhouse
    $325
    WEST STOCKBRIDGE
  5. Taylor Swift Travis Kelce Wedding Weekend Once in a Lifetime Event
    $500
    Wakefield
  6. WATERFRONT COTTAGE SPRING GETAWAYS GREAT RATES
    $150
    East Matunuck
  7. WATERFRONT COTTAGE SPRING GETAWAYS GREAT RATES
    $150
    East Matunuck
  8. WATERFRONT COTTAGE SPRING GETAWAYS GREAT RATES
    $150
    East Matunuck
  9. Beautifully Renovated Family Home
    $200
    4 Boice Rd, Egremont
  10. Beautiful Airy Space with Gorgeous Views of Hills, Gardens and Sky
    $850
    Williamsburg
  11. Western Massachusetts for upto 10 people near Berkshire East
    $269
    Plainfield, MA
  12. 1890 Farmhouse - fully renovated
    $275
    Adams
  13. ►FSBO Luxury Timeshare Ski Resort Condo (Week 52 & 7) at Jiminy Peak
    $1,000
    Hancock, MA
  14. Berkshire vacation rental in Plainfield Massachusetts
    $249
    Plainfield, MA
  15. Apartment 2 bedroom (rental for vacation only)
    $450
    springfield mass
  16. Summer house rental
    $4,000
    Lee
  17. Seabrook Beach september Weeks Discounted
    $1
    136 & 147 Franklin St 2-duplexes Gas grills/Outside showers
  18. Vacation Village in the Berkshires Sunday July 12-19 of 2026
    $1,295
    2-bedroom lockoff - 276 Brodie Mountain Rd - Hancock MA