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!

Use filters to narrow your search results!

Great Barrington: Houses, Cottages & More(87)

87 Results
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
#901004
(17)
3 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 11
#374330
30 - 31 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
#382742vb
1 Review
3 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
#3752845
3 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
#571468vb
2 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#423371vb
(20)
4 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
#500940vb
(3)
31 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
#186267
(3)
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
#148393
(12)
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
#414235vb
(14)
2 night minimum stay
  • 4 BR,
  • Sleeps 6
#171589
(16)
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
#3549728
2 Reviews
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 6
#573811vb
  • 1 BR,
  • 1 BA,
  • Sleeps 4
#269992
(10)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
#150942
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
#283395
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
#120394
  • 4 BR,
  • 3 BA,
  • Sleeps 10
#237517
  • 5 BR,
  • 2 BA,
  • Sleeps 10
#209775
2 Reviews
  • 4 BR,
  • 2 BA,
  • Sleeps 15
#3022555
1 Review
  • 1 BR,
  • 1 BA,
  • Sleeps 4
#218293
1 Review
2 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
#952910
(11)
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 9
#3528291
(7)
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
#566287vb
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 11
#3739831
2 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 10
#3692697
2 Reviews
$149 - $249
per night
1 - 2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
#3624808
(3)
2 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
#901996
(9)
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
#108941
(18)
2 - 7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 10
#101843
1 Review
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