Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Barns
Cabins
Cottages
Estates
Farmhouses
Homes
Apartments
Boats
Bungalows
Castles
Chalets
Condos
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Berkshires Mountain Vacation Rentals Vacation Rentals(50)

50 Results
  • 8 BR,
  • 5 BA,
  • Sleeps 14
    (5)
    5 night minimum stay
    • 3 BR,
    • 2 BA,
    • Sleeps 6
      (4)
      Book it Now!
      7 night minimum stay
      • 4 BR,
      • 3 BA,
      • Sleeps 9
        1 Review
        • 3 BR,
        • 2 BA,
        • Sleeps 7
          Book it Now!
          5 night minimum stay
          • 5 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 12
            Book it Now!
            7 night minimum stay
            • 2 BR,
            • 2 BA,
            • Sleeps 6
              7 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 8
                (4)
                3 night minimum stay
                • 4 BR,
                • 4 BA,
                • Sleeps 18
                  (3)
                  • 6 BR,
                  • 5 BA,
                  • 1 HF BA,
                  • Sleeps 18
                    3 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 8
                      (6)
                      30 - 31 night minimum stay
                      • 5 BR,
                      • 5 BA,
                      • Sleeps 15
                        • 5 BR,
                        • 3 BA,
                        • Sleeps 12
                          (15)
                          Book it Now!
                          7 night minimum stay
                          • 4 BR,
                          • 3 BA,
                          • Sleeps 8
                            (3)
                            Book it Now!
                            2 - 30 night minimum stay
                            • 5 BR,
                            • 4 BA,
                            • 1 HF BA,
                            • Sleeps 10
                              (8)
                              Book it Now!
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 9
                                2 night minimum stay
                                • 2 BR,
                                • 1 BA,
                                • Sleeps 6
                                  (17)
                                  3 - 7 night minimum stay
                                  • 3 BR,
                                  • 1 BA,
                                  • 1 HF BA,
                                  • Sleeps 6
                                    (16)
                                    2 night minimum stay
                                    • 3 BR,
                                    • 3 BA,
                                    • Sleeps 6
                                      (3)
                                      2 night minimum stay
                                      • 3 BR,
                                      • 1 BA,
                                      • Sleeps 6
                                        (8)
                                        2 night minimum stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 8
                                          (14)
                                          3 night minimum stay
                                          • 2 BR,
                                          • 2 BA,
                                          • Sleeps 10
                                            (7)
                                            $1,000 - $2,000
                                            per week
                                            7 - 14 night minimum stay
                                            • 4 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                              2 - 7 night minimum stay
                                              • 7 BR,
                                              • 5 BA,
                                              • 1 HF BA,
                                              • Sleeps 14
                                                2 Reviews
                                                $429 - $500
                                                per night
                                                6 - 10 night minimum stay
                                                • 4 BR,
                                                • 3 BA,
                                                • 1 HF BA,
                                                • Sleeps 8
                                                  2 Reviews
                                                  • 7 BR,
                                                  • 6 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 18
                                                    (13)
                                                    2 night minimum stay
                                                    • 3 BR,
                                                    • 1 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 6
                                                      2 night minimum stay
                                                      • 6 BR,
                                                      • 4 BA,
                                                      • Sleeps 12
                                                        2 Reviews
                                                        • 5 BR,
                                                        • 2 BA,
                                                        • Sleeps 9
                                                          2 Reviews
                                                          • 5 BR,
                                                          • 5 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 11
                                                            • 8 BR,
                                                            • 5 BA,
                                                            • Sleeps 16
                                                              1 Review
                                                               

                                                              Recent Berkshires Reviews

                                                              Perfect family getaway

                                                              5 of 5
                                                              This was the perfect summer getaway for our family. The house was spacious, yet cozy and comfortably accommodated three couples and an infant. Each couple had their own room and bathroom, and enough privacy (even the one in the loft space). The living space was great, kitchen had everything we needed and the pool was clean, well-maintained and perfect for the sunny days. We spent almost every meal on the large deck, dining outdoors and grilling. The view from this house, located atop a hill, was fantastic. You could see for miles across farmlands towards the mountains. The location of the house was also great. It felt secluded and private. It was a short or moderate drive to cute towns like Hudson and Great Barrington, farms/farmers markets, grocery stores, shops, hikes, etc. Also, it was just under a three hour drive from NYC. Alan was a lovely host, checking in with us periodically to ensure we had everything we needed and that we were enjoying our vacation. Our family could not have asked for a better experience for our summer getaway, and we will certainly be returning again!
                                                              • Submitted: Aug 21, 2014
                                                              • Stayed: Aug 2014

                                                              Cozy Cottage, Peaceful Setting

                                                              5 of 5
                                                              My family of five had a wonderful time in this lovely little cottage in the woods! The property is beautifully maintained and Fran has thought of everything that you might need while traveling away from home! It felt so homey. My kids loved staying up in the little loft. It was so comfortable and in such a peaceful setting with only the sounds of the nearby waterfall and chirping birds to help you relax and unwind from a busy life! We have family in the area and were in town for a reunion at nearby Lake Taghkanic Park. We will definitely be back and hope that the cottage is available when we return!
                                                              • Submitted: Jul 16, 2014
                                                              • Stayed: Jul 2014

                                                              Third Time Back

                                                              5 of 5
                                                              Obviously, three times renting, means we like it a lot! Quiet area, comfortable cottage, very nice owner, good fishing and golf. What else is there to say!
                                                              • Submitted: Jul 14, 2014
                                                              • Stayed: Jun 2014