check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar
Cancel Clear Filters Apply Filters

Property Type

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!
  • 1 - 50 of 86
Additional fees apply. Taxes may be added.
    • 3 BR
    • 1 BA
    • Sleeps 8
    31
      • 1 BR
      • 1 BA
      • Sleeps 4
      21
        NEW!
        • 5 BR
        • 3 BA
        • Sleeps 10
        1 Review
          • 3 BR
          • 2 BA
          • Sleeps 12
          26
            • 3 BR
            • 2 BA
            • Sleeps 7
            7
              NEW!
              • 3 BR
              • 1 BA
              • 1 HF BA
              • Sleeps 5
                • 5 BR
                • 3 BA
                • Sleeps 10
                2 Reviews
                  Exceptional! 5.0/5
                  (6 reviews)
                  avg/night
                  • 3 BR
                  • 2 BA
                  • 1 HF BA
                  • Sleeps 6
                  6
                    Wonderful! 4.9/5
                    (27 reviews)
                    avg/night
                    • 1 BR
                    • 1 BA
                    • Sleeps 3
                    27
                      • 4 BR
                      • 3 BA
                      • Sleeps 8
                      6
                        • 4 BR
                        • 2 BA
                        • 1 HF BA
                        • Sleeps 7
                        6
                          Exceptional! 5.0/5
                          (11 reviews)
                          avg/night
                          • 2 BR
                          • 2 BA
                          • 1 HF BA
                          • Sleeps 4
                          11
                            • 5 BR
                            • 3 BA
                            • 2 HF BA
                            • Sleeps 12
                            3
                              • 3 BR
                              • 2 BA
                              • Sleeps 8
                              5
                                • 4 BR
                                • 4 BA
                                • Sleeps 8
                                  • 4 BR
                                  • 3 BA
                                  • Sleeps 9
                                  5
                                    NEW!
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 8
                                      • 3 BR
                                      • 2 BA
                                      • 1 HF BA
                                      • Sleeps 8
                                      7
                                        Exceptional! 5.0/5
                                        (5 reviews)
                                        View details for price
                                        • 4 BR
                                        • 3 BA
                                        • Sleeps 9
                                        5
                                          • 4 BR
                                          • 3 BA
                                          • Sleeps 12
                                          9
                                            • 3 BR
                                            • 2 BA
                                            • 1 HF BA
                                            • Sleeps 7
                                            7
                                              Exceptional! 5.0/5
                                              (7 reviews)
                                              avg/night
                                              • 3 BR
                                              • 2 BA
                                              • Sleeps 8
                                              7
                                                • 3 BR
                                                • 2 BA
                                                • Sleeps 6
                                                  • 4 BR
                                                  • 6 BA
                                                  • Sleeps 9
                                                  7
                                                    • 3 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    2 Reviews
                                                      Wonderful! 4.8/5
                                                      (18 reviews)
                                                      avg/night
                                                      • 2 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      18
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        3
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 8
                                                          25
                                                            • 3 BR
                                                            • 2 BA
                                                            • 1 HF BA
                                                            • Sleeps 9
                                                            8
                                                              Excellent! 4.7/5
                                                              (7 reviews)
                                                              avg/night
                                                              • 3 BR
                                                              • 3 BA
                                                              • 1 HF BA
                                                              • Sleeps 10
                                                              7
                                                                • 3 BR
                                                                • 2 BA
                                                                • Sleeps 8
                                                                3
                                                                  • 4 BR
                                                                  • 2 BA
                                                                  • Sleeps 7
                                                                  11
                                                                    Exceptional! 5.0/5
                                                                    (7 reviews)
                                                                    avg/night
                                                                    • 3 BR
                                                                    • 2 BA
                                                                    • 1 HF BA
                                                                    • Sleeps 8
                                                                    7
                                                                      Wonderful! 4.9/5
                                                                      (8 reviews)
                                                                      avg/night
                                                                      • 4 BR
                                                                      • 2 BA
                                                                      • Sleeps 8
                                                                      8
                                                                        • 2 BR
                                                                        • 1 BA
                                                                        • Sleeps 4
                                                                          Excellent! 4.5/5
                                                                          (10 reviews)
                                                                          avg/night
                                                                          • 3 BR
                                                                          • 1 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 8
                                                                          10
                                                                            • 3 BR
                                                                            • 2 BA
                                                                            • Sleeps 6
                                                                            1 Review
                                                                              Excellent! 4.7/5
                                                                              (18 reviews)
                                                                              avg/night
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              18
                                                                                • 3 BR
                                                                                • 2 BA
                                                                                • Sleeps 6
                                                                                14
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • 1 HF BA
                                                                                  • Sleeps 11
                                                                                  3
                                                                                    Exceptional! 5.0/5
                                                                                    (6 reviews)
                                                                                    avg/night
                                                                                    • 3 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 6
                                                                                    6
                                                                                      Wonderful! 4.9/5
                                                                                      (9 reviews)
                                                                                      avg/night
                                                                                      • 3 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 7
                                                                                      9
                                                                                        • 3 BR
                                                                                        • 2 BA
                                                                                        • Sleeps 10
                                                                                          Wonderful! 4.9/5
                                                                                          (13 reviews)
                                                                                          avg/night
                                                                                          • 2 BR
                                                                                          • 2 BA
                                                                                          • Sleeps 6
                                                                                          13
                                                                                            • 3 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 9
                                                                                            3
                                                                                              • 3 BR
                                                                                              • 3 BA
                                                                                              • Sleeps 5
                                                                                                • 3 BR
                                                                                                • 1 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 6
                                                                                                8
                                                                                                  • 2 BR
                                                                                                  • 1 BA
                                                                                                  • 1 HF BA
                                                                                                  • Sleeps 6
                                                                                                  18
                                                                                                    Wonderful! 4.8/5
                                                                                                    (21 reviews)
                                                                                                    avg/night
                                                                                                    • 3 BR
                                                                                                    • 2 BA
                                                                                                    • Sleeps 11
                                                                                                    21
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 8
                                                                                                      35
                                                                                                      • 1 - 50 of 86
                                                                                                       

                                                                                                      Recent Pittsfield Reviews

                                                                                                      Peaceful Yet Convenient Location With Comfortable Spacious Accommodations In Beautiful Berkshires

                                                                                                      5 of 5
                                                                                                      This beautiful home was the perfect spot for our Book Club's annual gathering. Our gracious hostess has restored and renovated this historic schoolhouse by opening it up to the views of the surrounding Berkshire foothills. The home is tastefully decorated with beautiful handmade quilts, original paintings and even a few old fashioned schoolhouse motifs cleverly placed throughout the home. The outside grounds are spacious enough for an array of lawn games and are beautifully landscaped as well. We will certainly recommend this place to family and friends.
                                                                                                      • Submitted: Sep 28, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Terrific late September weekend spot!

                                                                                                      5 of 5
                                                                                                      Our group had a wedding in Lenox. This property is quaint, cozy and cute. Surrounded by great wooded areas, there was plenty of room to relax inside or outside. A+ home owner A+ property.
                                                                                                      • Submitted: Sep 26, 2016
                                                                                                      • Stayed: Sep 2016

                                                                                                      Beautiful Lake house!

                                                                                                      5 of 5
                                                                                                      Having never been to lake Ashmere, our expectations were not high. We wanted to be right on the water in a quiet setting in a comfortable and clean house. We got all of this and much more. Kayaking, canoeing, biking, swimming and leisurely walks were our daily activities and this doesn't even include reading by the Lake. The house was clean and had plenty of room for everyone. The back porch was a perfect place for coffee in the morning, lunch and a few games of gin rummy. We used the fire pit every night and even a few nights of S'more making. This was by far the most relaxing "staycation" we have ever had. We are already planning to book time next summer.
                                                                                                      • Submitted: Sep 24, 2016
                                                                                                      • Stayed: Aug 2016