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!

Pittsfield: Houses, Cottages & More (246)

  • 1 - 30 of 246
    • 1 BR
    • 1 BA
    • Sleeps 2
    2 Reviews
    Request to Book View Details
    24 hrs Confirmation within 24 hours
      • 2 BR
      • Sleeps 6
      19
        $126
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 5
        3
        Request to Book View Details
        24 hrs Confirmation within 24 hours
          View details for price
          • 4 BR
          • 1 BA
          • Sleeps 8
          2 Reviews
            • 3 BR
            • 2 BA
            • Sleeps 10
            2 Reviews
            Request to Book View Details
            24 hrs Confirmation within 24 hours
              • 3 BR
              • 2 BA
              • 1 HF BA
              • Sleeps 10
              Request to Book View Details
              24 hrs Confirmation within 24 hours
                • 2 BR
                • 1 BA
                • Sleeps 4
                5
                Request to Book View Details
                24 hrs Confirmation within 24 hours
                  • 3 BR
                  • 3 BA
                  • Sleeps 6
                  5
                  Request to Book View Details
                  24 hrs Confirmation within 24 hours
                    • 3 BR
                    • 2 BA
                    • Sleeps 12
                    7
                      • 3 BR
                      • 1 BA
                      • Sleeps 5
                      9
                      Request to Book View Details
                      24 hrs Confirmation within 24 hours
                        • 3 BR
                        • 2 BA
                        • Sleeps 6
                        10
                        Request to Book View Details
                        24 hrs Confirmation within 24 hours
                          • 2 BR
                          • Sleeps 5
                          15
                          Request to Book View Details
                          24 hrs Confirmation within 24 hours
                            • 3 BR
                            • 1 BA
                            • Sleeps 6
                            6
                            Request to Book View Details
                            24 hrs Confirmation within 24 hours
                              • 3 BR
                              • 1 BA
                              • Sleeps 6
                              3
                                • 2 BR
                                • 2 BA
                                • Sleeps 6
                                Request to Book View Details
                                24 hrs Confirmation within 24 hours
                                  • 3 BR
                                  • 2 BA
                                  • Sleeps 10
                                  4
                                    $224
                                    avg/night
                                    • 4 BR
                                    • 2 BA
                                    • Sleeps 8
                                    9
                                      • 3 BR
                                      • 1 BA
                                      • Sleeps 8
                                      9
                                      Request to Book View Details
                                      24 hrs Confirmation within 24 hours
                                        • 4 BR
                                        • 2 BA
                                        • Sleeps 10
                                        3
                                          • 4 BR
                                          • 2 BA
                                          • Sleeps 10
                                          4
                                            • 3 BR
                                            • 2 BA
                                            • Sleeps 7
                                            9
                                              $171
                                              avg/night
                                              • 3 BR
                                              • 1 BA
                                              • Sleeps 10
                                              6
                                              Request to Book View Details
                                              24 hrs Confirmation within 24 hours
                                                • 4 BR
                                                • 3 BA
                                                • Sleeps 10
                                                Request to Book View Details
                                                24 hrs Confirmation within 24 hours
                                                  • 5 BR
                                                  • 2 BA
                                                  • 1 HF BA
                                                  • Sleeps 15
                                                  1 Review
                                                    • 2 BR
                                                    • 1 BA
                                                    • Sleeps 6
                                                    16
                                                      • 3 BR
                                                      • 1 BA
                                                      • 1 HF BA
                                                      • Sleeps 7
                                                      4
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 8
                                                        4
                                                        Request to Book View Details
                                                        24 hrs Confirmation within 24 hours
                                                          • 4 BR
                                                          • 1 HF BA
                                                          • Sleeps 16
                                                          9
                                                          Request to Book View Details
                                                          24 hrs Confirmation within 24 hours
                                                            • 3 BR
                                                            • 2 BA
                                                            • Sleeps 8
                                                            40
                                                            Request to Book View Details
                                                            24 hrs Confirmation within 24 hours
                                                              • 3 BR
                                                              • 2 BA
                                                              • Sleeps 8
                                                              5
                                                              Request to Book View Details
                                                              24 hrs Confirmation within 24 hours
                                                              • 1 - 30 of 246
                                                               

                                                              Recent Pittsfield Reviews

                                                              pass wtays

                                                              5 of 5
                                                              Great place to stay for a week. The house has plenty of room and clean. A sandy beech is just down the street and the water is clean. You can catch alot of small fish close to the dock with worms. To catch the bigger ones you need to take the canoe across the lake. We are going this year for the forth time.
                                                              • Submitted: May 2, 2016
                                                              • Stayed: Aug 2015

                                                              Amazing is an understatement

                                                              5 of 5
                                                              My family and I had an AMAZING time renting this property. Location was perfect and the amenities in the house kept us more than busy for our stay. I don't have one bad thing to say about this property, owner was very responsive and accommodating which was VERY APPRECIATED. Any and all questions I had Sherri was more than willing to assist. House was very clean, spacious, everything was modern and welcoming, I absolutely LOVED this home and plan to rent again in the future.
                                                              • Submitted: Apr 25, 2016
                                                              • Stayed: Oct 2015

                                                              Great Place to spend a weekend

                                                              5 of 5
                                                              I spent a nice winter weekend with the wife and young son. The house was clean and very comfortable.
                                                              • Submitted: Feb 13, 2016
                                                              • Stayed: Feb 2016