Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Berkshires Vacation Rentals(230)

230 Results
Book it Now!
4 night minimum stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
    (10)
    2 - 7 night minimum stay
    • 6 BR,
    • 5 BA,
    • 1 HF BA,
    • Sleeps 16
      (8)
      $700 - $971
      per night
      Book it Now!
      3 - 7 night minimum stay
      • 5 BR,
      • 4 BA,
      • 1 HF BA,
      • Sleeps 11
        (6)
        Book it Now!
        3 - 4 night minimum stay
        • 4 BR,
        • 3 BA,
        • 1 HF BA,
        • Sleeps 12
          (5)
          Book it Now!
          2 - 7 night minimum stay
          • 3 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 10
            (3)
            1 - 2 night minimum stay
            • 1 BR,
            • 1 BA,
            • Sleeps 6
              (6)
              3 night minimum stay
              • 5 BR,
              • 5 BA,
              • 1 HF BA,
              • Sleeps 14
                (10)
                Book it Now!
                2 - 5 night minimum stay
                • 4 BR,
                • 3 BA,
                • Sleeps 15
                  (9)
                  3 - 7 night minimum stay
                  • 4 BR,
                  • 2 BA,
                  • Sleeps 8
                    (17)
                    $350 - $500
                    per night
                    Book it Now!
                    3 - 4 night minimum stay
                    • 4 BR,
                    • 3 BA,
                    • 1 HF BA,
                    • Sleeps 8
                      (5)
                      Book it Now!
                      2 - 3 night minimum stay
                      • 5 BR,
                      • 2 BA,
                      • Sleeps 10
                        (5)
                        7 night minimum stay
                        • 3 BR,
                        • 3 BA,
                        • Sleeps 8
                          (12)
                          • 4 BR,
                          • 2 BA,
                          • Sleeps 10
                            (12)
                            Book it Now!
                            2 night minimum stay
                            • 2 BR,
                            • 1 BA,
                            • Sleeps 5
                              Book it Now!
                              2 - 3 night minimum stay
                              • 2 BR,
                              • 2 BA,
                              • Sleeps 6
                                (16)
                                Book it Now!
                                2 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 8
                                  (7)
                                  2 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 7
                                    (7)
                                    4 - 7 night minimum stay
                                    • 3 BR,
                                    • 1 BA,
                                    • 1 HF BA,
                                    • Sleeps 6
                                      (3)
                                      Book it Now!
                                      2 - 4 night minimum stay
                                      • 4 BR,
                                      • 3 BA,
                                      • Sleeps 10
                                        (30)
                                        Book it Now!
                                        2 night minimum stay
                                        • 2 BR,
                                        • 1 BA,
                                        • Sleeps 6
                                          (14)
                                          2 night minimum stay
                                          • 4 BR,
                                          • 3 BA,
                                          • 1 HF BA,
                                          • Sleeps 12
                                            (17)
                                            2 night minimum stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                              (10)
                                              Book it Now!
                                              1 - 7 night minimum stay
                                              • 4 BR,
                                              • 2 BA,
                                              • Sleeps 12
                                                (4)
                                                2 night minimum stay
                                                • 1 BR,
                                                • 1 BA,
                                                • Sleeps 4
                                                  (10)
                                                  2 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 8
                                                    (9)
                                                    2 - 5 night minimum stay
                                                    • 3 BR,
                                                    • 2 BA,
                                                    • Sleeps 10
                                                      (30)
                                                      Book it Now!
                                                      2 - 3 night minimum stay
                                                      • 2 BR,
                                                      • 1 BA,
                                                      • Sleeps 6
                                                        1 Review
                                                        2 night minimum stay
                                                        • 4 BR,
                                                        • Sleeps 6
                                                          (16)
                                                          2 - 5 night minimum stay
                                                          • 4 BR,
                                                          • 2 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 8
                                                            2 Reviews
                                                            3 - 7 night minimum stay
                                                            • 2 BR,
                                                            • 2 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 8
                                                              (3)
                                                               

                                                              Recent Berkshires Reviews

                                                              The unusually exquisite architecture matched with

                                                              5 of 5
                                                              The unusually exquisite architecture matched with immaculate acres of landscaped property, pool, hot tub and sauna made are family of eight feel so pampered and comfortable. The kitchen and bathrooms were fully stocked. The house description did not begin to explain all that awaits you. We walked to Tanglewood. We were located in the center of everything. The owners were ready to help us out if anything was needed.We will tell all our friends about it and remember this vacation forever!
                                                              • Submitted: Aug 29, 2014
                                                              • Stayed: Aug 2014

                                                              Great Place!

                                                              5 of 5
                                                              Rental was lovely. Everything was immaculate. Convenient and so close to Lenox. Carmen is an ideal owner. She was so accommodation and easy to work with. Can't wait to stay here next year!
                                                              • Submitted: Aug 24, 2014
                                                              • Stayed: Aug 2014

                                                              a relaxing stay

                                                              5 of 5
                                                              Our family enjoyed a lovely stay at your home. All was as promised. Accurate listing description and amenities. Clean and well- maintained. Very good customer service, and we would recommend this property. We enjoyed a variety of restaurants, concerts, movies etc. The house is also a "destination" house for relaxing.
                                                              • Submitted: Aug 20, 2014
                                                              • Stayed: Aug 2014