Stay in Great Barrington Rentals for a Great Vacation Year-round

Great Barrington rentals, located in the Southern Berkshire Region of Massachusetts, offer a multitude of activities all year long for even the most discerning traveler. No matter which season brings you to the area, you’ll find an abundance of natural beauty and history packaged in this small town.

Enjoy the Mountains by Great Barrington Rentals


Surrounded by mountains and wildlife, Great Barrington vacation rentals give visitors a front row seat to the changing seasons and plants, as well as roaring waterfalls. Great Barrington, MA rentals offer easy access to mountain trails great for hiking and biking, and some may find opportunities for rockclimbing too.

Winter Sports near Great Barrington Vacation Rentals


Great Barrington rentals are great places to spend your winter break from school or work to rekindle relationships and spend quality time with your loved ones. Schedule a family reunion or get-together in the mountains for a fun ski and snowboarding trip; ice fishing and snow hiking are also great activities that will get your hearts pumping before enjoying a nice cup of hot chocolate in your Great Barrington vacation rentals.

It’s easy to fall in love with Great Barrington, MA rentals, and these may just become an annual destination due to the wide array of activities you’ll be able to pursue here!

Experience Local Culture in Great Barrington, MA Rentals


Your choice in Great Barrington rentals means that you may want to be located within walking distance of the greatest shopping and dining available, or so secluded that you may not see another person your entire stay. Groups of Great Barrington vacation rentals are perfect for extended family or friends that choose to experience the local culture together. Several antiques galleries, historical sites and performing arts centers will offer everyone something to do when staying in Great Barrington, MA rentals!

Looking for Berkshires rentals? Narrow down your search by destination: Becket apartments, Lee condos, Lenox rentals, and Stockbridge houses!

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Great Barrington Rentals(40)

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GREAT BARRINGTON
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  • Viewed
4 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 9

    No rental rates available - please contact the owner
    • Viewed
    4 Bedrooms, Sleeps 7

    $200 - $225 night
    $1,200 - $1,350 week
    $3,500 - $4,000 month
     
    Accepts HomeAway Payments℠
    HomeAway Payments℠ automatically protects you up to $10,000 against online identity theft.
    • Viewed
    4 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 10

    $250 - $475 night
    $950 - $2,400 week
    $4,200 month
     
    Accepts HomeAway Payments℠
    HomeAway Payments℠ automatically protects you up to $10,000 against online identity theft.
    • Viewed
    4 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 9

    $1,600 - $2,000 week
    $3,750 - $8,000 month
    • Viewed
    1 Bedrooms,
  • 1 Bathroom
  • , Sleeps 4

    $175 - $200 night
    $750 - $1,000 week
    $2,000 - $5,000 month
    • Viewed
    4 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 8

    $2,500 - $4,000 week
    $4,000 - $15,000 month
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 6

    $850 week
     
    Accepts HomeAway Payments℠
    HomeAway Payments℠ automatically protects you up to $10,000 against online identity theft.
    • Viewed
    2 Bedrooms,
  • 1 Bathroom
  • , Sleeps 6

    $975 week
    • Viewed
    4 Bedrooms,
  • 1 Bathroom
  • , 1 Half Bath
  • , Sleeps 8

    $800 - $1,600 week
    $2,600 - $6,000 month
     
    Accepts HomeAway Payments℠
    HomeAway Payments℠ automatically protects you up to $10,000 against online identity theft.
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 6

    $200 - $300 night
    $1,500 - $1,800 week
    $2,700 - $6,000 month
    • Viewed
    2 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 6

    $1,800 week
    $6,500 month
    • Viewed
    5 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 10

    $1,400 week
    $4,950 month
    • Viewed
    2 Bedrooms,
  • 1 Bathroom
  • , Sleeps 6

    $795 week
    $2,950 month
    • Viewed
    5 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 8

    $2,000 - $2,200 week
    $6,000 - $8,250 month
     
    Accepts HomeAway Payments℠
    HomeAway Payments℠ automatically protects you up to $10,000 against online identity theft.
    • Viewed
    2 Bedrooms,
  • 1 Bathroom
  • , 1 Half Bath
  • , Sleeps 6

    $1,700 week
    • Viewed
    5 Bedrooms,
  • 3 Bathrooms
  • , 1 Half Bath
  • , Sleeps 8

    $5,500 week
    $20,000 month
    • Viewed
    2 Bedrooms,
  • 1 Bathroom
  • , Sleeps 6

    No rental rates available - please contact the owner
    • Viewed
    1 Bedrooms,
  • 1 Bathroom
  • , Sleeps 2

    $130 - $160 night
    $675 - $950 week
    $1,250 - $2,600 month
    • Viewed
    4 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 9

    $1,500 - $2,000 week
    $5,000 - $8,000 month
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 6

    $900 week
    $3,200 month
     
    Accepts HomeAway Payments℠
    HomeAway Payments℠ automatically protects you up to $10,000 against online identity theft.
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 5

    $1,750 week
    • Viewed
    4 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 12

    $3,000 week
    • Viewed
    2 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 8

    $1,500 week
    $5,000 month
    • Viewed
    8 Bedrooms,
  • 4 Bathrooms
  • , 1 Half Bath
  • , Sleeps 18

    $1,200 night
    • Viewed
    4 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 10

    $1,200 - $2,250 week
    • Viewed
    1 Bedrooms,
  • 1 Bathroom
  • , Sleeps 4

    $100 - $175 night
    $600 - $650 week
    $2,000 - $2,500 month
    • Viewed
    2 Bedrooms,
  • 1 Bathroom
  • , Sleeps 6

    $2,000 month
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 8

    $1,000 - $2,000 week
    $3,000 - $6,000 month
    • Viewed
    3 Bedrooms,
  • 3 Bathrooms
  • , Sleeps 7

    No rental rates available - please contact the owner
    • Viewed
    3 Bedrooms,
  • 2 Bathrooms
  • , Sleeps 8

    No rental rates available - please contact the owner
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