Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Massachusetts Long Term Vacation Rental Estates(28)

28 Results
Book it Now!
1 - 7 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
    (9)
    $1,000 - $1,400
    per night
    Book it Now!
    6 - 7 night minimum stay
    • 4 BR,
    • 3 BA,
    • 1 HF BA,
    • Sleeps 14
      (9)
      2 - 7 night minimum stay
      • 4 BR,
      • 4 BA,
      • Sleeps 8
        (4)
        3 - 7 night minimum stay
        • 6 BR,
        • 4 BA,
        • 1 HF BA,
        • Sleeps 12
          (7)
          • 7 BR,
          • 5 BA,
          • 1 HF BA,
          • Sleeps 12
            1 - 7 night minimum stay
            • 3 BR,
            • 1 BA,
            • 1 HF BA,
            • Sleeps 6
              (5)
              3 - 7 night minimum stay
              • 5 BR,
              • 2 BA,
              • Sleeps 8
                (5)
                3 - 4 night minimum stay
                • 5 BR,
                • 4 BA,
                • 1 HF BA,
                • Sleeps 12
                  2 Reviews
                  Book it Now!
                  2 - 3 night minimum stay
                  • 5 BR,
                  • 2 BA,
                  • 2 HF BA,
                  • Sleeps 10
                    (3)
                    • 4 BR,
                    • 1 BA,
                    • 1 HF BA,
                    • Sleeps 6
                      Book it Now!
                      7 night minimum stay
                      • 4 BR,
                      • 2 BA,
                      • 2 HF BA,
                      • Sleeps 10
                        (3)
                        Book it Now!
                        3 night minimum stay
                        • 5 BR,
                        • 4 BA,
                        • 2 HF BA,
                        • Sleeps 10
                          Book it Now!
                          7 night minimum stay
                          • 5 BR,
                          • 7 BA,
                          • Sleeps 12
                            2 night minimum stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 8
                              (15)
                              2 - 3 night minimum stay
                              • 4 BR,
                              • 4 BA,
                              • 2 HF BA,
                              • Sleeps 8
                                7 night minimum stay
                                • 4 BR,
                                • 3 BA,
                                • Sleeps 12
                                  7 - 30 night minimum stay
                                  • 4 BR,
                                  • 2 BA,
                                  • Sleeps 5
                                    3 - 7 night minimum stay
                                    • 3 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 6
                                      14 night minimum stay
                                      • 7 BR,
                                      • 6 BA,
                                      • 1 HF BA,
                                      • Sleeps 14
                                        6 - 14 night minimum stay
                                        • 4 BR,
                                        • 2 BA,
                                        • 1 HF BA,
                                        • Sleeps 8
                                          14 night minimum stay
                                          • 5 BR,
                                          • 3 BA,
                                          • 2 HF BA,
                                          • Sleeps 10
                                            (11)
                                            3 - 7 night minimum stay
                                            • 2 BR,
                                            • 1 BA,
                                            • Sleeps 4
                                              2 night minimum stay
                                              • 4 BR,
                                              • 4 BA,
                                              • 1 HF BA,
                                              • Sleeps 8
                                                5 more choices from the HomeAway Network
                                                Book it Now!
                                                4 night minimum stay
                                                • 6 BR,
                                                • 6 BA,
                                                • Sleeps 12
                                                  2 Reviews
                                                  6 night minimum stay
                                                  • 6 BR,
                                                  • 2 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 12
                                                    7 night minimum stay
                                                    • 6 BR,
                                                    • 5 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 14
                                                      30 night minimum stay
                                                      • 5 BR,
                                                      • 3 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 11
                                                        5 night minimum stay
                                                        • 6 BR,
                                                        • 3 BA,
                                                        • 2 HF BA,
                                                        • Sleeps 10
                                                           

                                                          Recent Massachusetts Reviews

                                                          Beautiful Home, Great Amenities and Set up

                                                          4 of 5
                                                          We traveled to the Berkshires with our 22-month old son, and another family with an 8-month old son. This home was perfect - away from the town so we could relax and enjoy nature, but close enough (30 min) to Lenox for dinner out and walking around. The home is beautiful, and the kids loved the brook, as well as all the space outside to run/crawl around. The owner was very helpful and responsive. We cooked in for lunch and one dinner, and the house had everything we needed.
                                                          • Submitted: Sep 8, 2014
                                                          • Stayed: Aug 2014

                                                          Our Summer Home

                                                          5 of 5
                                                          We have been fortunate enough to vacation at this incredible home for 4 years now. Just driving up the dirt road to Malabar Farm feels like we're going to a little piece of our own home:) This is not your typical Rental Property....it is clearly a Home that is maintained and built with the utmost attention.... We finally brought our close family friend this year and although she enjoys 3 beautiful homes of her own....she was BLOWN AWAY the minute she stepped foot into the front door. We'll blink and it will be Aug 2015....we ALL look forward our home away from home....even if only for one week!
                                                          • Submitted: Aug 24, 2014
                                                          • Stayed: Aug 2014

                                                          Perfect Family Vacation Home

                                                          5 of 5
                                                          Our family of twelve had a wonderful vacation in the home of Jay and Maureen. We loved the beautiful view, so restful, and the town with friendly people all around. A perfect spot!
                                                          • Submitted: Aug 21, 2014
                                                          • Stayed: Aug 2014