Vacation Rentals & Apartments in Berkshires

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140 apartments

(4) Excellent 

    10

    Great Vacation House in the Berkshires by Richmond Pond

    Berkshires / Richmond

    Richmond house

    2 6 min stay varies

    • 2 bedrooms
    • sleeps 6
    • min stay varies
    • Beach / lakeside relaxation
    • Child Friendly
    • Air conditioning

    Price per night from

    $213

    Price per night from

    $213

    (4) Excellent 

      20

      Escape to the Berkshires!

      Berkshires / Becket

      Becket house

      4 8 2 nights min

      • 4 bedrooms
      • sleeps 8
      • 2 nights min
      • Child Friendly
      • Pet Friendly

      Price per night from

      $315

      Price per night from

      $315

      (1) Excellent 

        20

        Enjoy horses and the largest recreational lake in Massachusetts

        Berkshires / East Otis

        East Otis apartment

        1 4 1 night min

        • 1 bedroom
        • sleeps 4
        • 1 night min
        • Beach / lakeside relaxation
        • Child Friendly
        • Air conditioning

        Price per night from

        $126

        Price per night from

        $126

          5

          Cozy Modern Condo for the Berkshires

          Berkshires / West Stockbridge

          West Stockbridge condo

          2 6 1 night min

          • 2 bedrooms
          • sleeps 6
          • 1 night min
          • Child Friendly
          • Air conditioning
          • Pet Friendly

          Price per night from

          $287

          Responds fast!
          avg. 1 hour 18 minutes

          Price per night from

          $287

          (2) Excellent 

            41

            Apartment walking distance to Mass MoCa!!

            Berkshires / North Adams

            North Adams apartment

            2 10 min stay varies

            • 2 bedrooms
            • sleeps 10
            • min stay varies
            • Ski
            • Child Friendly
            • Car not necessary

            Price per night from

            $201

            Price per night from

            $201

              31

              Big Beautiful 7 bedroom 3 bath hot tub pool table

              Berkshires / Pittsfield

              Pittsfield house

              7 18 2 nights min

              • 7 bedrooms
              • sleeps 18
              • 2 nights min
              • Child Friendly
              • Ask about pets

              Price per night from

              $344

              Price per night from

              $344

              (4) Excellent 

                24

                Waterfront Cottage - 10 Mins to Great Barrington!

                Berkshires / New Marlborough

                New Marlborough cottage

                2 4 min stay varies

                • 2 bedrooms
                • sleeps 4
                • min stay varies
                • Ski

                Price per night from

                $207

                Responds fast!
                avg. 29 minutes

                Price per night from

                $207

                  14

                  Christmas in The Berkshires

                  Berkshires / Hancock

                  Hancock condo

                  1 4 2 nights min

                  • 1 bedroom
                  • sleeps 4
                  • 2 nights min
                  • Child Friendly

                  Price per night from

                  $258

                  Price per night from

                  $258

                    24

                    Cozy Jiminy Peak Area Condo w/Patio & Pool Access!

                    Berkshires / Hancock

                    Hancock apartment

                    2 6 min stay varies

                    • 2 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Swimming pool
                    • Ski
                    • Child Friendly

                    Price per night from

                    $212

                    Responds fast!
                    avg. 8 minutes

                    Price per night from

                    $212

                      18

                      Spacious wooded home

                      Berkshires / Becket

                      Becket house

                      4 12 3 nights min

                      • 4 bedrooms
                      • sleeps 12
                      • 3 nights min
                      • Beach / lakeside relaxation
                      • Private garden

                      Price per night from

                      $224

                      Price per night from

                      $224

                      (1) Excellent 

                        17

                        Restored 1886 Eyebrow Colonial

                        Berkshires / Stockbridge

                        Stockbridge house

                        2 6 7 nights min

                        • 2 bedrooms
                        • sleeps 6
                        • 7 nights min
                        • Child Friendly
                        • Air conditioning
                        • Private garden

                        Price per night from

                        $245

                        Price per night from

                        $245

                        (4) Excellent 

                          10

                          Comfortable Farmhouse in the Berkshires

                          Berkshires / West Stockbridge

                          West Stockbridge farmhouse

                          5 12 2 nights min

                          • 5 bedrooms
                          • sleeps 12
                          • 2 nights min
                          • Beach / lakeside relaxation
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $373

                          Price per night from

                          $373

                            24

                            Rustic Berkshires Cottage w/ Views of Lake Buel!

                            Berkshires / New Marlborough

                            New Marlborough cottage

                            1 2 7 nights min

                            • 1 bedroom
                            • sleeps 2
                            • 7 nights min
                            • Pet Friendly

                            Price per night from

                            $126

                            Responds fast!
                            avg. 8 minutes

                            Price per night from

                            $126

                              24

                              3BR Lee House w/ Easy Access to Main Street!

                              Berkshires / Lee

                              Lee house

                              3 10 min stay varies

                              • 3 bedrooms
                              • sleeps 10
                              • min stay varies
                              • Ski
                              • Child Friendly

                              Price per night from

                              $275

                              Responds fast!
                              avg. 29 minutes

                              Price per night from

                              $275

                              (3) Very Good 

                                14

                                2200sf Country House on 16 Acres-2 Miles to Jiminy

                                Berkshires / Hancock

                                Hancock house

                                4 9 2 nights min

                                • 4 bedrooms
                                • sleeps 9
                                • 2 nights min
                                • Child Friendly
                                • Pet Friendly
                                “Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope
                                …see more

                                Price per night from

                                $258

                                Price per night from

                                $258

                                  13

                                  Designer Loft Style Residence

                                  Berkshires / Sheffield

                                  Sheffield house

                                  3 6 7 nights min

                                  • 3 bedrooms
                                  • sleeps 6
                                  • 7 nights min
                                  • Child Friendly
                                  • Air conditioning
                                  • Pet Friendly

                                  Price per night from

                                  $516

                                  Responds fast!
                                  avg. 3 hours 46 minutes

                                  Price per night from

                                  $516

                                  (13) Very Good 

                                    13

                                    Quiet Comfortable Cabin 5 Min. Walk to Lake

                                    Berkshires / Becket

                                    Becket house

                                    2 4 2 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 2 nights min
                                    • Child Friendly
                                    • Air conditioning
                                    • Ask about pets
                                    “Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are
                                    …see more

                                    Price per night from

                                    $171

                                    Price per night from

                                    $171

                                      32

                                      Berkshire Home on Lake Garfield w/Dock & Boats

                                      Berkshires / Monterey

                                      Monterey house

                                      4 12 min stay varies

                                      • 4 bedrooms
                                      • sleeps 12
                                      • min stay varies
                                      • Ski
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $344

                                      Responds fast!
                                      avg. 29 minutes

                                      Price per night from

                                      $344

                                      (178) Excellent 

                                        37

                                        Unique People & Pet-Welcoming Country Haven

                                        Berkshires / Charlemont

                                        Charlemont apartment

                                        1 4 2 nights min

                                        • 1 bedroom
                                        • sleeps 4
                                        • 2 nights min
                                        • Child Friendly
                                        • Air conditioning
                                        • Pet Friendly
                                        “Cozy little spot, kid and definitely dog friendly” We brought our Cavalier with us and had a great time at the cottage. It was clean and gave us tons of room. Would definitely stay again.
                                        …see more

                                        Price per night from

                                        $149

                                        Price per night from

                                        $149

                                          24

                                          Beautiful Lakefront Berkshire Rental

                                          Berkshires / Monterey

                                          Monterey house

                                          5 6 7 nights min

                                          • 5 bedrooms
                                          • sleeps 6
                                          • 7 nights min
                                          • Beach / lakeside relaxation
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $489

                                          Price per night from

                                          $489

                                          (1) Excellent 

                                            21

                                            Lake House in Berkshires

                                            Berkshires / North Adams

                                            North Adams cottage

                                            1 2 2 nights min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 2 nights min

                                            Price per night from

                                            $121

                                            Price per night from

                                            $121

                                              7

                                              "The Barn" on Tower Mountain

                                              Berkshires / Hancock

                                              Hancock house

                                              2 5 2 nights min

                                              • 2 bedrooms
                                              • sleeps 5
                                              • 2 nights min

                                              Price per night from

                                              $172

                                              Price per night from

                                              $172

                                              (2) Excellent 

                                                8

                                                Cozy & Modern Home -mins from Tanglewood & Kripalu

                                                Berkshires / West Stockbridge

                                                West Stockbridge apartment

                                                2 6 1 night min

                                                • 2 bedrooms
                                                • sleeps 6
                                                • 1 night min
                                                • Ask about children
                                                • Air conditioning
                                                • Ask about pets

                                                Price per night from

                                                $115

                                                Responds fast!
                                                avg. 1 hour 18 minutes

                                                Price per night from

                                                $115

                                                (24) Excellent 

                                                  18

                                                  Berkshires: Romantic Cottage with spectacular view

                                                  Berkshires / Great Barrington

                                                  Great Barrington cottage

                                                  1 3 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 3
                                                  • min stay varies
                                                  • Nearest beach 2 mi
                                                  • Swimming pool
                                                  • Ask about children
                                                  “Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything loo
                                                  …see more

                                                  Price per night from

                                                  $228

                                                  Price per night from

                                                  $228

                                                  (5) Excellent 

                                                    31

                                                    Berkshires Waterfront Lakehouse Sanctuary

                                                    Berkshires / Lanesboro

                                                    Lanesboro house

                                                    3 6 2 nights min

                                                    • 3 bedrooms
                                                    • sleeps 6
                                                    • 2 nights min
                                                    • Beach / lakeside relaxation
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $224

                                                    Responds fast!
                                                    avg. 3 hours 22 minutes

                                                    Price per night from

                                                    $224

                                                    (2) Average 

                                                      27

                                                      Shaker Hill

                                                      Berkshires / Great Barrington

                                                      Great Barrington house

                                                      5 10 3 nights min

                                                      • 5 bedrooms
                                                      • sleeps 10
                                                      • 3 nights min
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $430

                                                      Price per night from

                                                      $430

                                                        23

                                                        Spacious Lakeside Berkshire Home

                                                        Berkshires / Monterey

                                                        Monterey house

                                                        4 10 3 nights min

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • 3 nights min
                                                        • Child Friendly
                                                        • Air conditioning
                                                        • Private garden

                                                        Price per night from

                                                        $458

                                                        Price per night from

                                                        $458

                                                        (17) Excellent 

                                                          10

                                                          Stone School Cottage

                                                          Berkshires / Lanesboro

                                                          Lanesboro cottage

                                                          2 5 2 nights min

                                                          • 2 bedrooms
                                                          • sleeps 5
                                                          • 2 nights min
                                                          • Child Friendly
                                                          • Air conditioning
                                                          • Private garden
                                                          “A wonderful experience” My parents really enjoyed their stay. They said everything was wonderful. It is a very charming and has wonderful history. They really thought the baby horses playing in the field across the street was an over the top touch.
                                                          …see more

                                                          Price per night from

                                                          $178

                                                          Responds fast!
                                                          avg. 2 hours 42 minutes

                                                          Price per night from

                                                          $178

                                                            8

                                                            New Timberframe House Rental in the Berkshire Mountains, Masschusetts

                                                            Berkshires / Hinsdale

                                                            Hinsdale house

                                                            3 6 2 nights min

                                                            • 3 bedrooms
                                                            • sleeps 6
                                                            • 2 nights min
                                                            • Child Friendly
                                                            • Ask about pets
                                                            • Private garden

                                                            Price per night from

                                                            $166

                                                            Price per night from

                                                            $166

                                                            (4) Excellent 

                                                              30

                                                              Gem of the Berkshires, walk to downtown & lake.

                                                              Berkshires / Great Barrington

                                                              Great Barrington house

                                                              5 12 2 nights min

                                                              • 5 bedrooms
                                                              • sleeps 12
                                                              • 2 nights min
                                                              • Nearest beach 0.32 mi
                                                              • Child Friendly
                                                              • Air conditioning
                                                              “Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are b
                                                              …see more

                                                              Price per night from

                                                              $344

                                                              Price per night from

                                                              $344

                                                                24

                                                                NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

                                                                Berkshires / Lenox

                                                                Lenox house

                                                                3 6 3 nights min

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • 3 nights min
                                                                • Child Friendly

                                                                Price per night from

                                                                $264

                                                                Responds fast!
                                                                avg. 29 minutes

                                                                Price per night from

                                                                $264

                                                                  17

                                                                  House On Main Street

                                                                  Berkshires / Williamstown

                                                                  Williamstown house

                                                                  4 16 2 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 16
                                                                  • 2 nights min
                                                                  • Child Friendly
                                                                  • Car not necessary
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $573

                                                                  Responds fast!
                                                                  avg. 1 hour 19 minutes

                                                                  Price per night from

                                                                  $573

                                                                  (30) Excellent 

                                                                    21

                                                                    Gartner House, a charming home in Lenox

                                                                    Berkshires / Lenox

                                                                    Lenox apartment

                                                                    4 7 2 nights min

                                                                    • 4 bedrooms
                                                                    • sleeps 7
                                                                    • 2 nights min
                                                                    • Child Friendly
                                                                    • Car not necessary
                                                                    • Ask about pets
                                                                    “Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa,
                                                                    …see more

                                                                    Price per night from

                                                                    $229

                                                                    Price per night from

                                                                    $229

                                                                    (2) Excellent 

                                                                      24

                                                                      Country Elegance in the Berkshires

                                                                      Berkshires / Great Barrington

                                                                      Great Barrington house

                                                                      4 12 2 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 12
                                                                      • 2 nights min
                                                                      • Nearest beach 0 mi
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $745

                                                                      Responds fast!
                                                                      avg. 2 hours 46 minutes

                                                                      Price per night from

                                                                      $745

                                                                      (1) Excellent 

                                                                        24

                                                                        'Butterfly Hill' West Stockbridge Home on 3 Acres!

                                                                        Berkshires / West Stockbridge

                                                                        West Stockbridge house

                                                                        2 4 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • min stay varies
                                                                        • Ski
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $189

                                                                        Responds fast!
                                                                        avg. 29 minutes

                                                                        Price per night from

                                                                        $189

                                                                          12

                                                                          Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

                                                                          Berkshires / Lee

                                                                          Lee apartment

                                                                          2 6 2 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • 2 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $430

                                                                          Price per night from

                                                                          $430

                                                                          (14) Excellent 

                                                                          Certificate of Excellence

                                                                            55

                                                                            RiverSong Suite In The Berkshires

                                                                            Berkshires / North Egremont

                                                                            North Egremont apartment

                                                                            1 2 1 night min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 1 night min
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 2 mi
                                                                            • Air conditioning

                                                                            Certificate of Excellence

                                                                            Price per night from

                                                                            $217

                                                                            Responds fast!
                                                                            avg. 33 minutes

                                                                            Price per night from

                                                                            $217

                                                                              18

                                                                              Historic Home on 8.5 Acres

                                                                              Berkshires / Dalton

                                                                              Dalton house

                                                                              3 9 3 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 9
                                                                              • 3 nights min
                                                                              • Swimming pool
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $458

                                                                              Price per night from

                                                                              $458

                                                                              About Berkshires

                                                                              A Berkshires getaway in the Berkshire Mountains of Massachusetts is the perfect way to escape the bustle of everyday life and experience breathtaking natural beauty. Get the most out of your time here by staying in a vacation rental, such as a secluded cabin in the woods. Wake up in your vacation rental to the sound of birds and forest life, and enjoy coffee on your private balcony as the sun rises. Then wander downtown to explore the shops, local museums, and unique independent art galleries. In the afternoon, head for the trails to hike to cascading waterfalls, experience a Berkshires zip line adventure, or take an ATV tour. At the end of a busy day, retreat to your home away from home and host a barbeque or a game night for your family and friends.

                                                                              Here are a few additional suggestions for your trip:

                                                                              • Go horseback riding: There are several well-maintained stables in the Berkshires area that offer lessons or guided single and multi-day trail rides.
                                                                              • Take a snowmobiling lesson: During the winter, the back country trails through the mountains are perfect for snowmobiling. Take a lesson or join a group adventure.
                                                                              • Go skiing or snowshoeing: Cross country skis offer a quieter way to explore the pristine snowy trails and increase opportunities to spot elusive wildlife like foxes and black bears.
                                                                              • Go fishing: Take a fly fishing trip along the winding, hidden waterways, or rent a boat and cast your line in the lake at sunrise.
                                                                              • Spend an afternoon in the spa: Indulge in a day of pampering at a Berkshires spa with a manicure, pedicure, or hot rock massage.
                                                                              • Play golf: Tee off at any one of several champion caliber, emerald green golf courses throughout the Berkshires region.

                                                                              No matter what activities you have in mind for your vacation or what time of year you plan to visit the Berkshires, you'll find endless things to do here, and the best way to enjoy it all is with your own private vacation rental. Find a cabin or condo that offers all the luxury amenities you and your family need, then relax, unwind, and make great vacation memories. While you're in the Berkshires, you may also want to visit the coast and explore the historic villages of Cape Cod.