Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Barns
Bungalows
Cabins
Chalets
Condos
Cottages
Estates
Farmhouses
Hotels
Homes
Studios
Townhomes
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 Cottage Rentals(66)

66 Results
  • 2 BR,
  • 1 BA,
  • Sleeps 6
    (10)
    2 night minimum stay
    • 2 BR,
    • 1 BA,
    • Sleeps 4
      (10)
      2 - 3 night minimum stay
      • 3 BR,
      • 1 BA,
      • Sleeps 7
        2 - 30 night minimum stay
        • 2 BR,
        • 1 BA,
        • Sleeps 6
          • 3 BR,
          • 2 BA,
          • Sleeps 6
            2 Reviews
            7 night minimum stay
            • 2 BR,
            • 1 BA,
            • Sleeps 6
              2 night minimum stay
              • 1 BR,
              • 1 BA,
              • Sleeps 4
                (3)
                • 4 BR,
                • 2 BA,
                • Sleeps 8
                  1 Review
                  28 more choices from the HomeAway Network
                  Book it Now!
                  • 4 BR,
                  • 3 BA,
                  • Sleeps 8
                    Book it Now!
                    2 - 7 night minimum stay
                    • 4 BR,
                    • 1 BA,
                    • 1 HF BA,
                    • Sleeps 7
                      (7)
                      Book it Now!
                      2 - 3 night minimum stay
                      • 1 BR,
                      • 1 BA,
                      • Sleeps 6
                        (4)
                        Book it Now!
                        2 - 3 night minimum stay
                        • Studio,
                        • 1 BA,
                        • Sleeps 2
                          (3)
                          Book it Now!
                          • 3 BR,
                          • 1 BA,
                          • Sleeps 6
                            1 Review
                            Book it Now!
                            2 - 31 night minimum stay
                            • 2 BR,
                            • 1 BA,
                            • Sleeps 4
                              Book it Now!
                              2 night minimum stay
                              • 2 BR,
                              • 1 BA,
                              • Sleeps 4
                                1 Review
                                3 - 7 night minimum stay
                                • 2 BR,
                                • 1 BA,
                                • Sleeps 4
                                  (7)
                                  $160 - $200
                                  per night
                                  Book it Now!
                                  2 - 5 night minimum stay
                                  • 1 BR,
                                  • 1 BA,
                                  • 1 HF BA,
                                  • Sleeps 4
                                    (5)
                                    Book it Now!
                                    4 - 6 night minimum stay
                                    • 2 BR,
                                    • 1 BA,
                                    • Sleeps 6
                                      2 Reviews
                                      Book it Now!
                                      2 - 3 night minimum stay
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 6
                                        2 Reviews
                                        2 night minimum stay
                                        • 2 BR,
                                        • 1 BA,
                                        • Sleeps 4
                                          (11)
                                          3 - 7 night minimum stay
                                          • 4 BR,
                                          • 2 BA,
                                          • Sleeps 8
                                            3 night minimum stay
                                            • 2 BR,
                                            • 1 BA,
                                            • Sleeps 4
                                              (18)
                                              2 - 14 night minimum stay
                                              • 2 BR,
                                              • 1 BA,
                                              • Sleeps 4
                                                14 night minimum stay
                                                • 2 BR,
                                                • 2 BA,
                                                • Sleeps 5
                                                  Book it Now!
                                                  2 night minimum stay
                                                  • 2 BR,
                                                  • 1 BA,
                                                  • Sleeps 6
                                                    (3)
                                                    • 1 BR,
                                                    • 1 BA,
                                                    • Sleeps 2
                                                      (8)
                                                      3 - 7 night minimum stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • Sleeps 8
                                                        $250 - $300
                                                        per night
                                                        2 - 3 night minimum stay
                                                        • 2 BR,
                                                        • 1 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 6
                                                          2 - 7 night minimum stay
                                                          • 4 BR,
                                                          • 1 BA,
                                                          • Sleeps 10
                                                            (5)
                                                            2 night minimum stay
                                                            • 1 BR,
                                                            • 1 BA,
                                                            • Sleeps 2
                                                              1 Review
                                                               

                                                              Recent Berkshires Reviews

                                                              Great Family Get-Away!

                                                              5 of 5
                                                              We had such a great time in this lovely cottage. The owners were very helpful and welcoming, the amenities had everything we needed, the location is perfect for getting away but being central to lots of fun day trips. We really enjoyed the fire pit, grill, and our 4-year-old son loved the yard. We're looking for dates now to rebook!
                                                              • Submitted: Jul 29, 2014
                                                              • Stayed: Jul 2014

                                                              Quiet, Peaceful and Just Lovely

                                                              5 of 5
                                                              First off, the cottage is just lovely. The pictures do not do it justice. It has a rustic old-time feel to it and it is much much larger than the pictures make it look. There are lots of beds and it is clean and cozy. We wished there was at least one queen sized bed, but we had a bit of a good time putting two beds together and occasionally slipping through them in the middle of the night (I guess we are easily amused that way). We brought our three dogs with us and they just loved it, too. It's a little hike to the water, but it has a private dock, row boat, canoe and more. Lots of little amenities that make it so comfortable regardless of the hike downhill (which we did not mind at all; we would alternate between driving down and walking down with the dogs). The owners, Denise and Chad, are just two of the loveliest people we've met. The emails and conversations I exchanged with Denise before getting there made me know early on that she would be great. But once we got there we were just delighted by how friendly and accommodating both she and Chad were. Just lovely people. Wish we had more of them here in Brooklyn! I highly recommend staying here. You will truly enjoy it!
                                                              • Submitted: Sep 25, 2013
                                                              • Stayed: Aug 2013

                                                              A bit of heaven

                                                              5 of 5
                                                              Second year at this beautiful bit of heaven.... Another tough day trying to decide what to do.... Sit on the porch and watch the sheep.drifting by, take a long walk on a country road, go to the farmers market and bring home some veggies,,,read a book. Listen to the birds chirp.....hmmmm We have been coming to the berkshires for 40 years and never get enough of it.. Mayflower farm is a treasure!
                                                              • Submitted: Jul 11, 2012
                                                              • Stayed: Jul 2012