Let Lenox Rentals Liven up Your Berkshire Vacation

Lenox, Massachusetts is a charming little art-loving town situated in the heart of the famous Berkshire Mountain area of the state. The town is filled with quaint old churches, art galleries and cafes, and all of it is accessible from most Lenox rentals with ease. There are plenty of museums, old homes, and cultural activities to take in that will make a memorable mountain vacation for the whole family.

Lenox, MA Vacation Rentals and the Arts


If the arts are what you love, Lenox, MA vacation rentals are the ideal destinations for you. Spend a day visiting the Ventfort Hall Museum of the Gilded Age to get a little taste of history and art of times past. It is a Gilded Age mansion that will take your breath away. If you love music, leave your Lenox, Berkshires rentals to visit Tanglewood; the summer home to the Boston Symphony Orchestra. If literature is more your fancy, Mount Estate and Gardens of Edith Wharton allow you to step out of your Lenox rentals and into a beautiful mansion and formal gardens designed by the Pulitzer-Prize winning novelist herself.

Lenox Rentals and the Great Outdoors


A trip involving Lenox, MA vacation rentals means that there are also plenty of outdoor activities at your fingertips. The Undermountain Farm Riding Stable allows for horseback riding lessons, schooling shows, and pony rides for the kids. For more adventure, you could check out what Berkshire Horseback Adventures has to offer. Be sure to spend a day outside from your Lenox, Berkshires rentals at the Pleasant Valley Wildlife Sanctuary to take in some beautiful wildlife including flora and fauna laid out over seven miles of trails on 1,500 acres.

Learn a Little Staying at Lenox, Berkshires Rentals


Just because you are on vacation does not mean you cannot learn a thing or two. The Lenox Athenaeum offers seminars on theater, dance, literature, classical music, and other subjects, just minutes away from most Lenox rentals. It also offers a variety of charitable functions, recitals, and private performances to promote history, art, and literature appreciation, which is a great way to spend the evenings away from your Lenox, Berkshires rentals. You may also find that you might enjoy a night away from your Lenox, MA vacation rentals at the Shakespeare & Company Theater Group. There are free outdoor family performances as well as indoor stages.

Looking for Berkshires rentals? Narrow down your search by destination: Becket apartments, Great Barrington condos, Lee condos, and Stockbridge houses!

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Lenox: Houses, Condos & More(54)

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Charming, spacious country home with stunning views.....steps from Tanglewood!
    5 Bedrooms,
  • 5 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 14
$885 - $1,500
per night

Charming, spacious country home with stunning views.....steps from Tanglewood!

3 night Minimum Stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
  1. Berkshires >
  2. Lenox Chalet
#923721
    (6)
    Charming Berkshire Victorian in Lenox, Ma - Walk to Tanglewood
      6 Bedrooms,
    • 2 Bathrooms, 
    • 2 Half Baths
      • , Sleeps 10

    Charming Berkshire Victorian in Lenox, Ma - Walk to Tanglewood

    • 6 BR,
    • 2 BA,
    • 2 HF BA,
    • Sleeps 10
    1. Berkshires >
    2. Lenox Farmhouse
    #350655
      (5)
      Beautifully Renovated Barn With Pool
        4 Bedrooms,
      • 2 Bathrooms, 
      • 1 Half Bath
        • , Sleeps 8
      $250 - $1,000
      per night

      Beautifully Renovated Barn With Pool

      2 night Minimum Stay
      • 4 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 8
      1. Berkshires >
      2. Lenox House
      #3537906
        Exclusive Property
          2 Bedrooms,
        • 1 Bathroom, 
        • 1 Half Bath
          • , Sleeps 4
        $2,275
        per week

        Exclusive Property

        Book it Now!
        7 night Minimum Stay
        • 2 BR,
        • 1 BA,
        • 1 HF BA,
        • Sleeps 4
        1. Berkshires >
        2. Lenox House
        #3548734
          Lenox -- Cozy cottage in woods, 5 min. from Tanglewood, beach
            3 Bedrooms,
          • 1 Bathroom, 
          • 1 Half Bath
            • , Sleeps 7
          $952 - $1,246
          per week

          Lenox -- Cozy cottage in woods, 5 min. from Tanglewood, beach

          7 night Minimum Stay
          • 3 BR,
          • 1 BA,
          • 1 HF BA,
          • Sleeps 7
          1. Berkshires >
          2. Lenox Cabin
          #130835
            (4)
            Soho Chic meets Historic Charmer, Walk to town & Abutting Nature Preserve
              4 Bedrooms,
            • 4 Bathrooms
              • , Sleeps 8
            $695 - $795
            per night

            Soho Chic meets Historic Charmer, Walk to town & Abutting Nature Preserve

            2 - 7 night Minimum Stay
            • 4 BR,
            • 4 BA,
            • Sleeps 8
            1. Berkshires >
            2. Lenox House
            #237736
              (16)
              'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox
                5 Bedrooms,
              • 3 Bathrooms
                • , Sleeps 9
              $2,800 - $3,800
              per week

              'Village View'- Elegant, Comfortable, Historic Home in Downtown Lenox

              2 - 7 night Minimum Stay
              • 5 BR,
              • 3 BA,
              • Sleeps 9
              1. Berkshires >
              2. Lenox House
              #156305
                (31)
                Newly Renovated Home in a quiet Lenox Neighborhood.
                  2 Bedrooms,
                • 2 Bathrooms, 
                • 1 Half Bath
                  • , Sleeps 4
                $1,200 - $1,500
                per week

                Newly Renovated Home in a quiet Lenox Neighborhood.

                7 night Minimum Stay
                • 2 BR,
                • 2 BA,
                • 1 HF BA,
                • Sleeps 4
                1. Berkshires >
                2. Lenox House
                #3002071
                  (3)
                  Townhouse in heart of Lenox
                    3 Bedrooms,
                  • 2 Bathrooms
                    • , Sleeps 6
                  $2,100
                  per week

                  Townhouse in heart of Lenox

                  7 night Minimum Stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 6
                  1. Berkshires >
                  2. Lenox Townhome
                  #3498317
                    Townhouse in Lenox Center
                      3 Bedrooms, Sleeps 6
                    $2,100
                    per week

                    Townhouse in Lenox Center

                    7 night Minimum Stay
                    • 3 BR,
                    • Sleeps 6
                    1. Berkshires >
                    2. Lenox Townhome
                    #3497694
                      Lovely Colonial on 10 acres-Walk to Tanglewood and Historic Lenox Village
                        3 Bedrooms,
                      • 3 Bathrooms, 
                      • 1 Half Bath
                        • , Sleeps 6
                      $450
                      per night

                      Lovely Colonial on 10 acres-Walk to Tanglewood and Historic Lenox Village

                      2 night Minimum Stay
                      • 3 BR,
                      • 3 BA,
                      • 1 HF BA,
                      • Sleeps 6
                      1. Berkshires >
                      2. Lenox House
                      #288088
                        1 Review
                        Tranquil Waterfront Lenox Cottage, min to Tanglewood/Village Berkshire
                          2 Bedrooms,
                        • 1 Bathroom, 
                        • 1 Half Bath
                          • , Sleeps 4
                        $1,100 - $1,500
                        per week

                        Tranquil Waterfront Lenox Cottage, min to Tanglewood/Village Berkshire

                        7 night Minimum Stay
                        • 2 BR,
                        • 1 BA,
                        • 1 HF BA,
                        • Sleeps 4
                        1. Berkshires >
                        2. Lenox Cottage
                        #157193
                          (8)
                          Unique Condo, Quiet Neighborhood, Walk to Town.
                            2 Bedrooms,
                          • 2 Bathrooms
                            • , Sleeps 4
                          $115 - $225
                          per night

                          Unique Condo, Quiet Neighborhood, Walk to Town.

                          2 night Minimum Stay
                          • 2 BR,
                          • 2 BA,
                          • Sleeps 4
                          1. Berkshires >
                          2. Lenox Condo
                          #134366
                            (12)
                            Private Setting in Lenox
                              3 Bedrooms,
                            • 2 Bathrooms
                              • , Sleeps 6
                            $1,500 - $2,800
                            per week

                            Private Setting in Lenox

                            2 night Minimum Stay
                            • 3 BR,
                            • 2 BA,
                            • Sleeps 6
                            1. Berkshires >
                            2. Lenox House
                            #207123
                              (3)
                              Charming 200 year old completely renovated farm house on sprawling 5 acres
                                4 Bedrooms,
                              • 3 Bathrooms
                                • , Sleeps 8
                              $1,000
                              per night

                              Charming 200 year old completely renovated farm house on sprawling 5 acres

                              2 - 7 night Minimum Stay
                              • 4 BR,
                              • 3 BA,
                              • Sleeps 8
                              1. Berkshires >
                              2. Lenox Farmhouse
                              #332248
                                1 Review
                                Stunning Contemporary Colonial with Two En-Suite Master Bedrooms
                                  4 Bedrooms, Sleeps 8
                                $300
                                per night

                                Stunning Contemporary Colonial with Two En-Suite Master Bedrooms

                                2 - 28 night Minimum Stay
                                • 4 BR,
                                • Sleeps 8
                                1. Berkshires >
                                2. Lenox House
                                #388430
                                  Lovingly Cared 4, Ranch- 1 level- Piano,Private deck. Ask rent price.
                                    2 Bedrooms,
                                  • 2 Bathrooms
                                    • , Sleeps 6
                                  $250
                                  per night

                                  Lovingly Cared 4, Ranch- 1 level- Piano,Private deck. Ask rent price.

                                  4 night Minimum Stay
                                  • 2 BR,
                                  • 2 BA,
                                  • Sleeps 6
                                  1. Berkshires >
                                  2. Lenox House
                                  #113603
                                    Your Own B&B with babbling brook and Berkshire mountain views
                                      14 Bedrooms,
                                    • 13 Bathrooms, 
                                    • 1 Half Bath
                                      • , Sleeps 36

                                    Your Own B&B with babbling brook and Berkshire mountain views

                                    • 14 BR,
                                    • 13 BA,
                                    • 1 HF BA,
                                    • Sleeps 36
                                    1. Berkshires >
                                    2. Lenox House
                                    #932208
                                      (7)
                                      Country home directly across from Tanglewood main gate w/ 1st floor Master Suite
                                        7 Bedrooms,
                                      • 5 Bathrooms, 
                                      • 1 Half Bath
                                        • , Sleeps 14
                                      $1,000
                                      per night

                                      Country home directly across from Tanglewood main gate w/ 1st floor Master Suite

                                      2 night Minimum Stay
                                      • 7 BR,
                                      • 5 BA,
                                      • 1 HF BA,
                                      • Sleeps 14
                                      1. Berkshires >
                                      2. Lenox Farmhouse
                                      #253180
                                        1 Review
                                        Lovely Lenox Colonial with mountain views yet one mile from center of town
                                          4 Bedrooms,
                                        • 3 Bathrooms
                                          • , Sleeps 9
                                        $4,000
                                        per week

                                        Lovely Lenox Colonial with mountain views yet one mile from center of town

                                        2 night Minimum Stay
                                        • 4 BR,
                                        • 3 BA,
                                        • Sleeps 9
                                        1. Berkshires >
                                        2. Lenox House
                                        #174313
                                          1 Review
                                          Luxury Lenox home near Tanglewood & Jacobs Pillow & all Berkshire attractions
                                            3 Bedrooms,
                                          • 2 Bathrooms, 
                                          • 1 Half Bath
                                            • , Sleeps 8
                                          $6,720
                                          per month

                                          Luxury Lenox home near Tanglewood & Jacobs Pillow & all Berkshire attractions

                                          14 night Minimum Stay
                                          • 3 BR,
                                          • 2 BA,
                                          • 1 HF BA,
                                          • Sleeps 8
                                          1. Berkshires >
                                          2. Lenox House
                                          #230771
                                            2 Reviews
                                            Lenox Lakefront Rental House for Fall 2013
                                              3 Bedrooms,
                                            • 2 Bathrooms
                                              • , Sleeps 6
                                            $1,500
                                            per week

                                            Lenox Lakefront Rental House for Fall 2013

                                            7 - 28 night Minimum Stay
                                            • 3 BR,
                                            • 2 BA,
                                            • Sleeps 6
                                            1. Berkshires >
                                            2. Lenox House
                                            #365314
                                              2 Reviews
                                              Charming Lenox Home walk to town and close to Tanglewood
                                                3 Bedrooms,
                                              • 1 Bathroom
                                                • , Sleeps 6
                                              $225 - $275
                                              per night

                                              Charming Lenox Home walk to town and close to Tanglewood

                                              2 night Minimum Stay
                                              • 3 BR,
                                              • 1 BA,
                                              • Sleeps 6
                                              1. Berkshires >
                                              2. Lenox House
                                              #185249
                                                (7)
                                                5 MIN TO DINING, 10 MIN TO SKIING, ...$2,500/3 NIGHTS, $4,000/WEEK*
                                                  4 Bedrooms,
                                                • 3 Bathrooms, 
                                                • 1 Half Bath
                                                  • , Sleeps 10
                                                $800 - $1,000
                                                per night

                                                5 MIN TO DINING, 10 MIN TO SKIING, ...$2,500/3 NIGHTS, $4,000/WEEK*

                                                3 - 7 night Minimum Stay
                                                • 4 BR,
                                                • 3 BA,
                                                • 1 HF BA,
                                                • Sleeps 10
                                                1. Berkshires >
                                                2. Lenox House
                                                #973913
                                                  1 Review
                                                  SHERWOOD HOUSE - Lovely modern 2 bdrm near Tanglewood, Town Center & Lake
                                                    2 Bedrooms,
                                                  • 2 Bathrooms
                                                    • , Sleeps 6

                                                  SHERWOOD HOUSE - Lovely modern 2 bdrm near Tanglewood, Town Center & Lake

                                                  • 2 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                  1. Berkshires >
                                                  2. Lenox House
                                                  #200829
                                                    1 Review
                                                    Lenox - Wonderful home in village
                                                      3 Bedrooms,
                                                    • 2 Bathrooms, 
                                                    • 1 Half Bath
                                                      • , Sleeps 5

                                                    Lenox - Wonderful home in village

                                                    • 3 BR,
                                                    • 2 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 5
                                                    1. Berkshires >
                                                    2. Lenox House
                                                    #158350
                                                      2 Reviews
                                                      New Luxury Townhouse Less Than 5 Minutes from Lenox, MA and Tanglewood.
                                                        4 Bedrooms,
                                                      • 3 Bathrooms, 
                                                      • 1 Half Bath
                                                        • , Sleeps 8

                                                      New Luxury Townhouse Less Than 5 Minutes from Lenox, MA and Tanglewood.

                                                      • 4 BR,
                                                      • 3 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 8
                                                      1. Berkshires >
                                                      2. Lenox Townhome
                                                      #235509
                                                        Charming Cottage, Private Lenox Location
                                                          4 Bedrooms,
                                                        • 2 Bathrooms
                                                          • , Sleeps 8
                                                        $1,200 - $1,600
                                                        per week

                                                        Charming Cottage, Private Lenox Location

                                                        3 - 7 night Minimum Stay
                                                        • 4 BR,
                                                        • 2 BA,
                                                        • Sleeps 8
                                                        1. Berkshires >
                                                        2. Lenox Cottage
                                                        #121670
                                                          1 Review
                                                          Elegant 3500 sq foot country Tudor home with swimming pool on 12.5 wooded acres
                                                            4 Bedrooms,
                                                          • 2 Bathrooms, 
                                                          • 1 Half Bath
                                                            • , Sleeps 8
                                                          $1,500
                                                          per week

                                                          Elegant 3500 sq foot country Tudor home with swimming pool on 12.5 wooded acres

                                                          14 - 28 night Minimum Stay
                                                          • 4 BR,
                                                          • 2 BA,
                                                          • 1 HF BA,
                                                          • Sleeps 8
                                                          1. Berkshires >
                                                          2. Lenox Estate
                                                          #208300
                                                            1 Review
                                                            GREAT in Town Location-Near Tanglewood, SKIING
                                                              2 Bedrooms,
                                                            • 1 Bathroom
                                                              • , Sleeps 3
                                                            $1,150 - $3,500
                                                            per month

                                                            GREAT in Town Location-Near Tanglewood, SKIING

                                                            56 - 84 night Minimum Stay
                                                            • 2 BR,
                                                            • 1 BA,
                                                            • Sleeps 3
                                                            1. Berkshires >
                                                            2. Lenox
                                                            #246444
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