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: Houses, Cottages & More(82)

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Berkshires Mid-century Hideaway; Private, Yet Close To Town
    2 Bedrooms,
  • 2 Bathrooms
    • , Sleeps 6
$285 - $350
per night

Berkshires Mid-century Hideaway; Private, Yet Close To Town

Book it Now!
2 night Minimum Stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
  1. Berkshires >
  2. Great Barrington House
#423371vb
    (8)
    Berkshires weekend getaway. Stunning View. Walk to lake & downtown.
      4 Bedrooms,
    • 3 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 12
    $450 - $600
    per night

    Berkshires weekend getaway. Stunning View. Walk to lake & downtown.

    2 night Minimum Stay
    • 4 BR,
    • 3 BA,
    • 1 HF BA,
    • Sleeps 12
    1. Berkshires >
    2. Great Barrington Cottage
    #414235vb
      (9)
      Beautiful 1920's Colonial 20 Minutes from Tanglewood
        4 Bedrooms,
      • 1 Bathroom, 
      • 1 Half Bath
        • , Sleeps 8
      $800 - $1,600
      per week

      Beautiful 1920's Colonial 20 Minutes from Tanglewood

      2 - 7 night Minimum Stay
      • 4 BR,
      • 1 BA,
      • 1 HF BA,
      • Sleeps 8
      1. Berkshires >
      2. Great Barrington House
      #901004
        (11)
        BEAUTIFULLY RENOVATED LAKE BUEL COTTAGE
          2 Bedrooms,
        • 1 Bathroom
          • , Sleeps 6
        $200
        per night

        BEAUTIFULLY RENOVATED LAKE BUEL COTTAGE

        2 night Minimum Stay
        • 2 BR,
        • 1 BA,
        • Sleeps 6
        1. Berkshires >
        2. Great Barrington House
        #148393
          (10)
          Walk to Town Home 'On The Hill'
            4 Bedrooms,
          • 3 Bathrooms
            • , Sleeps 12
          $3,010
          per week

          Walk to Town Home 'On The Hill'

          7 night Minimum Stay
          • 4 BR,
          • 3 BA,
          • Sleeps 12
          1. Berkshires >
          2. Great Barrington House
          #283395
            Charming cottage, near beautiful Lake Buel, child and pet friendly
              4 Bedrooms, Sleeps 7
            $225
            per night

            Charming cottage, near beautiful Lake Buel, child and pet friendly

            2 night Minimum Stay
            • 4 BR,
            • Sleeps 7
            1. Berkshires >
            2. Great Barrington Cottage
            #171589
              (14)
              Quiet luxury retreat, incredible views, near cultural & recreational attractions
                3 Bedrooms,
              • 2 Bathrooms
                • , Sleeps 8
              $2,100
              per week

              Quiet luxury retreat, incredible views, near cultural & recreational attractions

              7 night Minimum Stay
              • 3 BR,
              • 2 BA,
              • Sleeps 8
              1. Berkshires >
              2. Great Barrington House
              #3549728
                Historic Country Home
                  3 Bedrooms,
                • 2 Bathrooms
                  • , Sleeps 5
                $250
                per night

                Historic Country Home

                2 night Minimum Stay
                • 3 BR,
                • 2 BA,
                • Sleeps 5
                1. Berkshires >
                2. Great Barrington House
                #251868
                  1 Review
                  Family vacation home in Great Barrington
                    4 Bedrooms,
                  • 3 Bathrooms
                    • , Sleeps 10
                  $1,500 - $2,000
                  per week

                  Family vacation home in Great Barrington

                  7 night Minimum Stay
                  • 4 BR,
                  • 3 BA,
                  • Sleeps 10
                  1. Berkshires >
                  2. Great Barrington House
                  #237517
                    Lake Cottage Waiting for You! Near Town, Attractions
                      2 Bedrooms, Sleeps 6

                    Lake Cottage Waiting for You! Near Town, Attractions

                    • 2 BR,
                    • Sleeps 6
                    1. Berkshires >
                    2. Great Barrington House
                    #118766
                      (13)
                      Elegant, Private, 4 bedroom, Berkshires Home on 10 acres
                        4 Bedrooms,
                      • 3 Bathrooms, 
                      • 1 Half Bath
                        • , Sleeps 9

                      Elegant, Private, 4 bedroom, Berkshires Home on 10 acres

                      • 4 BR,
                      • 3 BA,
                      • 1 HF BA,
                      • Sleeps 9
                      1. Berkshires >
                      2. Great Barrington House
                      #120394
                        New Contemporary Log Home with Boat Dock/Butternut Ski Basin Screened Porch
                          4 Bedrooms,
                        • 3 Bathrooms
                          • , Sleeps 9

                        New Contemporary Log Home with Boat Dock/Butternut Ski Basin Screened Porch

                        • 4 BR,
                        • 3 BA,
                        • Sleeps 9
                        1. Berkshires >
                        2. Great Barrington House
                        #150942
                          family friendly,child friendly, pet friendly,
                            4 Bedrooms,
                          • 2 Bathrooms
                            • , Sleeps 15

                          family friendly,child friendly, pet friendly,

                          • 4 BR,
                          • 2 BA,
                          • Sleeps 15
                          1. Berkshires >
                          2. Great Barrington House
                          #3022555
                            Berkshire Pied a Terre
                              1 Bedrooms,
                            • 1 Bathroom
                              • , Sleeps 4

                            Berkshire Pied a Terre

                            • 1 BR,
                            • 1 BA,
                            • Sleeps 4
                            1. Berkshires >
                            2. Great Barrington Apartment
                            #218293
                              1 Review
                              Pond, Orchard. Near Tanglewood, Gt. Barrington. Air conditioned.
                                5 Bedrooms,
                              • 2 Bathrooms, 
                              • 1 Half Bath
                                • , Sleeps 7
                              $3,900 - $6,417
                              per month

                              Pond, Orchard. Near Tanglewood, Gt. Barrington. Air conditioned.

                              30 night Minimum Stay
                              • 5 BR,
                              • 2 BA,
                              • 1 HF BA,
                              • Sleeps 7
                              1. Berkshires >
                              2. Great Barrington House
                              #3000644
                                Kid And Pet Friendly Home Away From Home
                                  3 Bedrooms,
                                • 3 Bathrooms
                                  • , Sleeps 9
                                $200 - $350
                                per night

                                Kid And Pet Friendly Home Away From Home

                                Book it Now!
                                4 - 7 night Minimum Stay
                                • 3 BR,
                                • 3 BA,
                                • Sleeps 9
                                1. Berkshires >
                                2. Great Barrington Cabin
                                #3528291
                                  3000 Sq Ft Ski House One Half Mile to Ski Butternut
                                    3 Bedrooms,
                                  • 2 Bathrooms
                                    • , Sleeps 6
                                  $250
                                  per night

                                  3000 Sq Ft Ski House One Half Mile to Ski Butternut

                                  2 - 30 night Minimum Stay
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                  1. Berkshires >
                                  2. Great Barrington House
                                  #901996
                                    (7)
                                    Field View Cottage , convenient to all Berkshire attractions
                                      4 Bedrooms,
                                    • 2 Bathrooms
                                      • , Sleeps 9
                                    $300 - $375
                                    per night

                                    Field View Cottage , convenient to all Berkshire attractions

                                    2 night Minimum Stay
                                    • 4 BR,
                                    • 2 BA,
                                    • Sleeps 9
                                    1. Berkshires >
                                    2. Great Barrington House
                                    #952910
                                      (8)
                                      Idyllic Berkshire Get Away: Balance of relaxation and convenience
                                        3 Bedrooms,
                                      • 2 Bathrooms
                                        • , Sleeps 6
                                      $1,000
                                      per week

                                      Idyllic Berkshire Get Away: Balance of relaxation and convenience

                                      7 - 84 night Minimum Stay
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                      1. Berkshires >
                                      2. Great Barrington House
                                      #237215
                                        2 Reviews
                                        All Year Lakefront House in Berkshires- Ideal for Summer/Fall Foliage
                                          5 Bedrooms,
                                        • 3 Bathrooms
                                          • , Sleeps 11
                                        $300 - $350
                                        per night

                                        All Year Lakefront House in Berkshires- Ideal for Summer/Fall Foliage

                                        2 - 7 night Minimum Stay
                                        • 5 BR,
                                        • 3 BA,
                                        • Sleeps 11
                                        1. Berkshires >
                                        2. Great Barrington House
                                        #100101
                                          1 Review
                                          Time to plan for the Summer - June and September still open
                                            5 Bedrooms,
                                          • 2 Bathrooms
                                            • , Sleeps 8
                                          $2,000 - $2,200
                                          per week

                                          Time to plan for the Summer - June and September still open

                                          2 - 6 night Minimum Stay
                                          • 5 BR,
                                          • 2 BA,
                                          • Sleeps 8
                                          1. Berkshires >
                                          2. Great Barrington Estate
                                          #101843
                                            1 Review
                                            Detached studio apartment in private, convenient, woodland setting
                                              1 Bedrooms,
                                            • 1 Bathroom
                                              • , Sleeps 4
                                            $175 - $200
                                            per night

                                            Detached studio apartment in private, convenient, woodland setting

                                            2 - 7 night Minimum Stay
                                            • 1 BR,
                                            • 1 BA,
                                            • Sleeps 4
                                            1. Berkshires >
                                            2. Great Barrington Studio
                                            #269992
                                              (9)
                                              Berkshires, Lake Buel, Beautiful Cottage,Walk 2 Private Dock Beach
                                                2 Bedrooms,
                                              • 1 Bathroom
                                                • , Sleeps 6
                                              $175 - $215
                                              per night

                                              Berkshires, Lake Buel, Beautiful Cottage,Walk 2 Private Dock Beach

                                              2 night Minimum Stay
                                              • 2 BR,
                                              • 1 BA,
                                              • Sleeps 6
                                              1. Berkshires >
                                              2. Great Barrington Cottage
                                              #3540285
                                                Berkshires, Lake Buel, Private Waterfront
                                                  2 Bedrooms,
                                                • 1 Bathroom, 
                                                • 1 Half Bath
                                                  • , Sleeps 6
                                                $245 - $250
                                                per night

                                                Berkshires, Lake Buel, Private Waterfront

                                                3 - 7 night Minimum Stay
                                                • 2 BR,
                                                • 1 BA,
                                                • 1 HF BA,
                                                • Sleeps 6
                                                1. Berkshires >
                                                2. Great Barrington Cottage
                                                #183642
                                                  (9)
                                                  Rustic Secluded Hilltop Carriage House
                                                    3 Bedrooms,
                                                  • 2 Bathrooms
                                                    • , Sleeps 8
                                                  $500
                                                  per night

                                                  Rustic Secluded Hilltop Carriage House

                                                  2 night Minimum Stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 8
                                                  1. Berkshires >
                                                  2. Great Barrington House
                                                  #100299
                                                    (29)
                                                    Berkshire Sanctuary: Apartment Suite in The Carriage House
                                                      1 Bedrooms,
                                                    • 1 Bathroom
                                                      • , Sleeps 2
                                                    $130 - $165
                                                    per night

                                                    Berkshire Sanctuary: Apartment Suite in The Carriage House

                                                    2 night Minimum Stay
                                                    • 1 BR,
                                                    • 1 BA,
                                                    • Sleeps 2
                                                    1. Berkshires >
                                                    2. Great Barrington Apartment
                                                    #122925
                                                      (10)
                                                      Bright Sunny Berkshire Home- Beautiful Sunsets
                                                        2 Bedrooms,
                                                      • 2 Bathrooms
                                                        • , Sleeps 8

                                                      Bright Sunny Berkshire Home- Beautiful Sunsets

                                                      • 2 BR,
                                                      • 2 BA,
                                                      • Sleeps 8
                                                      1. Berkshires >
                                                      2. Great Barrington House
                                                      #186835
                                                        quiet, updated, wifi, scenic, birds, walking trails, clean, bright
                                                          Studio,

                                                        quiet, updated, wifi, scenic, birds, walking trails, clean, bright

                                                        • Studio
                                                        1. Berkshires >
                                                        2. Great Barrington
                                                        #3006259
                                                          2 Reviews
                                                          Fabulous GB Estate w/ Pool, Hot Tub, Views, 120 acres + Guest House!
                                                            9 Bedrooms,
                                                          • 6 Bathrooms, 
                                                          • 1 Half Bath
                                                            • , Sleeps 20
                                                          $13,000 - $15,000
                                                          per week

                                                          Fabulous GB Estate w/ Pool, Hot Tub, Views, 120 acres + Guest House!

                                                          2 night Minimum Stay
                                                          • 9 BR,
                                                          • 6 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 20
                                                          1. Berkshires >
                                                          2. Great Barrington Estate
                                                          #3020119
                                                            Adorable 2 BR Bungalow with Every Attention Made for your Comfort!
                                                              2 Bedrooms,
                                                            • 1 Bathroom, 
                                                            • 1 Half Bath
                                                              • , Sleeps 6

                                                            Adorable 2 BR Bungalow with Every Attention Made for your Comfort!

                                                            • 2 BR,
                                                            • 1 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 6
                                                            1. Berkshires >
                                                            2. Great Barrington House
                                                            #456324vb
                                                              • 1 - 30 of 82
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