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(42)

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GREAT BARRINGTON
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HomeAway Sort is based on both the type of subscription purchased and property listing criteria. Criteria include items such as number of photos and reviews that are aimed at simplifying the process of finding your perfect vacation getaway.
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  • Viewed
4 Bedrooms, 3 Bathrooms, Sleeps 10

$250 - $475 night
$950 - $2,400 week
Accepts Online Payments
  • Viewed
4 Bedrooms, 2 Bathrooms, Sleeps 9

$1,600 - $2,000 week
$3,700 - $8,000 month
  • Viewed
2 Bedrooms, 2 Bathrooms, Sleeps 6

$1,800 week
$3,500 - $6,500 month
  • Viewed
2 Bedrooms, 1 Bathroom, 1 Half Bath, Sleeps 6

$1,700 - $1,800 week
  • Viewed
4 Bedrooms, 2 Bathrooms, Sleeps 8

$2,500 - $4,000 week
$4,000 - $15,000 month
  • Viewed
2 Bedrooms, 1 Bathroom, Sleeps 6

No rental rates available - please contact the owner
  • Viewed
1 Bedrooms, 1 Bathroom, Sleeps 4

$175 - $200 night
$750 week
$2,000 month
  • Viewed
2 Bedrooms, 1 Bathroom, Sleeps 6

$975 week
  • Viewed
5 Bedrooms, 2 Bathrooms, Sleeps 8

$2,000 - $2,200 week
$3,500 - $8,250 month
Accepts Online Payments
  • Viewed
3 Bedrooms, 2 Bathrooms, Sleeps 6

$850 week
$2,500 month
  • Viewed
2 Bedrooms, 1 Bathroom, Sleeps 6

$795 week
$2,950 month
  • Viewed
3 Bedrooms, 2 Bathrooms, Sleeps 6

$900 week
$1,500 - $3,200 month
Accepts Online Payments
  • Viewed
4 Bedrooms, 1 Bathroom, 1 Half Bath, Sleeps 8

$800 - $1,600 week
$3,000 - $6,000 month
Accepts Online Payments
  • Viewed
3 Bedrooms, 2 Bathrooms, Sleeps 6

$200 - $300 night
$1,500 - $1,800 week
$2,700 - $6,000 month
  • Viewed
2 Bedrooms, 1 Bathroom, Sleeps 4

No rental rates available - please contact the owner
Accepts Online Payments
  • Viewed
8 Bedrooms, 4 Bathrooms, 1 Half Bath, Sleeps 18

$1,200 night
  • Viewed
3 Bedrooms, 1 Bathroom, 1 Half Bath, Sleeps 5

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

$1,000 - $2,800 week
$3,500 - $10,000 month
  • Viewed
5 Bedrooms, 2 Bathrooms, Sleeps 10

$325 night
$2,800 week
$5,500 month
  • Viewed
1 Bedrooms, 1 Bathroom, Sleeps 2

$125 night
$650 week
$1,500 month
  • Viewed
5 Bedrooms, 3 Bathrooms, 1 Half Bath, Sleeps 8

$5,500 week
$20,000 month
  • Viewed
4 Bedrooms, 3 Bathrooms, Sleeps 12

$3,000 week
  • Viewed
4 Bedrooms, 3 Bathrooms, Sleeps 10

$1,200 - $2,000 week
  • Viewed
3 Bedrooms, 2 Bathrooms, Sleeps 5

$1,750 week
  • Viewed
5 Bedrooms, 3 Bathrooms, 1 Half Bath, Sleeps 11

No rental rates available - please contact the owner
  • Viewed
2 Bedrooms, 1 Bathroom, Sleeps 6

$2,000 month
  • Viewed
3 Bedrooms, 3 Bathrooms, Sleeps 7

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

$1,500 week
$4,000 month
  • Viewed
3 Bedrooms, 2 Bathrooms, Sleeps 8

No rental rates available - please contact the owner
  • Viewed
3 Bedrooms, 3 Bathrooms, 1 Half Bath, Sleeps 7

No rental rates available - please contact the owner
Sort Properties By: 
HomeAway Sort is based on both the type of subscription purchased and property listing criteria. Criteria include items such as number of photos and reviews that are aimed at simplifying the process of finding your perfect vacation getaway.
Compare Selected