Massies Mill Rentals

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72 Houses

(3) Excellent 

    30

    Cottage at Massies Mill & the Blue Ridge Mountains

    Virginia / Massies Mill

    Massies Mill cottage

    3 6 2 nights min

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

    Price per night from

    $172

    Responds fast!
    avg. 2 hours 40 minutes

    Price per night from

    $172

    Great rentals within 20 miles that match your search

    Distance approx 10.13 km from Massies Mill

      27

      Updated Wintergreen Resort Home w/ Mountain Views!

      Virginia / Wintergreen

      Wintergreen house

      3 7 min stay varies

      • 3 bedrooms
      • sleeps 7
      • min stay varies
      • Swimming pool
      • Ski
      • Child Friendly

      Price per night from

      $241

      Responds fast!
      avg. 20 minutes

      Price per night from

      $241

      Distance approx 17.43 km from Massies Mill

      (12) Excellent 

        22

        Blueberry Hill Farm in Historic Shenandoah Valley

        Virginia / Staunton

        Staunton apartment

        1 3 2 nights min

        • 1 bedroom
        • sleeps 3
        • 2 nights min
        • Car not necessary
        • Air conditioning
        “Excellent "headquarter" for exploring Shenandoah” We stayed for a week and was very satisfied with both location and the room and its facilities. Their was always a nice place to sit outside and enjoy the landscape or read regardless of the weather -
        …see more

        Price per night from

        $103

        Price per night from

        $103

        Distance approx 9.75 km from Massies Mill

        (7) Very Good 

          30

          Pet Friendly 2BR House in Blue Ridge Mtns, Close to Blue Ridge Parkway

          Virginia / Lyndhurst

          Lyndhurst house

          2 6 2 nights min

          • 2 bedrooms
          • sleeps 6
          • 2 nights min
          • Nearest beach 21 mi
          • Swimming pool
          • Child Friendly
          “Cute and relaxing getaway” The cabin had such character and was extremely comfortable to stay in with a small kitchen, sufficient to meet the needs of a long weekend or week, two grill areas, and very relaxing. It is a ture log cabin in that there re
          …see more

          Price per night from

          $171

          Responds fast!
          avg. 2 hours 12 minutes

          Price per night from

          $171

          Distance approx 5.93 km from Massies Mill Show on Map

          (2) Excellent 

            22

            Escape to Campbell's Creek

            Virginia / Tyro

            Tyro log cabin

            2 5 2 nights min

            • 2 bedrooms
            • sleeps 5
            • 2 nights min
            • Child Friendly

            Price per night from

            $287

            Price per night from

            $287

            Distance approx 9.66 km from Massies Mill

              13

              Rock-n-Creek Cabin mile post 27 off BR Pkwy

              Virginia / Montebello

              Montebello log cabin

              3 11 2 nights min

              • 3 bedrooms
              • sleeps 11
              • 2 nights min
              • Child Friendly
              • Air conditioning
              • Pet Friendly

              Price per night from

              $224

              Price per night from

              $224

              Distance approx 10.15 km from Massies Mill

              (2) Excellent 

                22

                3BR Wintergreen House w/Private Decks!

                Virginia / Wintergreen

                Wintergreen house

                3 8 min stay varies

                • 3 bedrooms
                • sleeps 8
                • min stay varies
                • Ski
                • Child Friendly
                • Air conditioning

                Price per night from

                $212

                Responds fast!
                avg. 20 minutes

                Price per night from

                $212

                Distance approx 14.76 km from Massies Mill

                  29

                  Afton Home w/ Huge Deck - Near Wineries/Breweries!

                  Virginia / Afton

                  Afton house

                  9 24 min stay varies

                  • 9 bedrooms
                  • sleeps 24
                  • min stay varies
                  • Ski
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $572

                  Responds fast!
                  avg. 20 minutes

                  Price per night from

                  $572

                  Distance approx 10.91 km from Massies Mill

                  (7) Excellent 

                    13

                    Christmas Available: Luxury Mountain House w/ Resort Membership

                    Virginia / Wintergreen

                    Wintergreen house

                    3 8 min stay varies

                    • 3 bedrooms
                    • sleeps 8
                    • min stay varies
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning
                    “Mountain Resort in Va” Cozy ski getaway or family retreat. Soaring wood ceilings and stone fireplace; huge windows. Lovely views of lush green lawn and several tall trees. Peaceful and quiet. Huge kitchen and dining area, full amenites, and very clean
                    …see more

                    Price per night from

                    $304

                    Responds fast!
                    avg. 2 hours 59 minutes

                    Price per night from

                    $304

                    Distance approx 9.25 km from Massies Mill

                    (1) Excellent 

                      9

                      The Mountain House

                      Virginia / Wintergreen

                      Wintergreen house

                      5 12 2 nights min

                      • 5 bedrooms
                      • sleeps 12
                      • 2 nights min
                      • Nearest beach 16 mi
                      • Swimming pool
                      • Child Friendly
                      “A wonderful stay” Our family traveled to Barbara's home to enjoy a relaxing getaway and celebrate a college graduation! The house is equipped with everything you need- comfortable beds and immaculate. I would give it a 5.- and know that we will look
                      …see more

                      Price per night from

                      $315

                      Responds fast!
                      avg. 2 hours 9 minutes

                      Price per night from

                      $315

                      Distance approx 12.6 km from Massies Mill

                      (1) Excellent 

                        25

                        Lyndhurst Log Cabin on Farm w/Pond+Stocked Stream!

                        Virginia / Lyndhurst

                        Lyndhurst log cabin

                        1 6 min stay varies

                        • 1 bedroom
                        • sleeps 6
                        • min stay varies
                        • Ski
                        • Child Friendly

                        Price per night from

                        $172

                        Responds fast!
                        avg. 20 minutes

                        Price per night from

                        $172

                        Distance approx 8.58 km from Massies Mill Show on Map

                        (1) Excellent 

                          11

                          Second Creek Farm near Blue Ridge Parkway in Virg

                          Virginia / Montebello

                          Montebello 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

                          Price per night from

                          $224

                          Distance approx 10.64 km from Massies Mill

                            26

                            Wintergreen Cabin w/Private Hot Tub, Deck & Views!

                            Virginia / Wintergreen

                            Wintergreen house

                            3 8 min stay varies

                            • 3 bedrooms
                            • sleeps 8
                            • min stay varies
                            • Swimming pool
                            • Ski
                            • Child Friendly

                            Price per night from

                            $247

                            Responds fast!
                            avg. 20 minutes

                            Price per night from

                            $247

                            Distance approx 9.82 km from Massies Mill

                            (1) Excellent 

                              20

                              Secluded 2BR Pet-Friendly Cabin on Mountain Stream-Screen Porch

                              Virginia / Wintergreen

                              Wintergreen log cabin

                              2 4 2 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 2 nights min
                              • Nearest beach 3 mi
                              • Swimming pool
                              • Child Friendly
                              “Great get away for us and our dog!” Wonderful cabin, great location! Cabin was spotless, and well appointed. Loved the gas fireplace and screened porch. Can't wait to return to Cabin Creekwood!
                              …see more

                              Price per night from

                              $171

                              Responds fast!
                              avg. 2 hours 12 minutes

                              Price per night from

                              $171

                              Distance approx 15.25 km from Massies Mill

                              (3) Excellent 

                                17

                                Rose Cottage at Steeles Tavern

                                Virginia / Lexington

                                Lexington house

                                3 6 2 nights min

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

                                Price per night from

                                $184

                                Responds fast!
                                avg. 2 hours 57 minutes

                                Price per night from

                                $184

                                Distance approx 9.66 km from Massies Mill

                                  24

                                  NEW! Cozy Wintergreen Resort Home - Walk to Lifts!

                                  Virginia / Wintergreen

                                  Wintergreen townhouse

                                  2 5 min stay varies

                                  • 2 bedrooms
                                  • sleeps 5
                                  • min stay varies
                                  • Swimming pool
                                  • Ski
                                  • Child Friendly

                                  Price per night from

                                  $161

                                  Responds fast!
                                  avg. 11 minutes

                                  Price per night from

                                  $161

                                  Distance approx 10.9 km from Massies Mill

                                  (1) Excellent 

                                    21

                                    The Retreat at Wintergreen

                                    Virginia / Wintergreen

                                    Wintergreen house

                                    4 12 3 nights min

                                    • 4 bedrooms
                                    • sleeps 12
                                    • 3 nights min
                                    • Ski
                                    • Child Friendly
                                    • Private garden

                                    Price per night from

                                    $453

                                    Price per night from

                                    $453

                                    Distance approx 9.23 km from Massies Mill

                                    (4) Very Good 

                                      26

                                      Private Pet-Friendly 3BR Blue Ridge Mtn Cabin - Huge Deck

                                      Virginia / Charlottesville

                                      Charlottesville log cabin

                                      3 8 2 nights min

                                      • 3 bedrooms
                                      • sleeps 8
                                      • 2 nights min
                                      • Nearest beach 3 mi
                                      • Swimming pool
                                      • Child Friendly
                                      “Wonderful cabin on the Blue Ridge Parkway” Staying at this cabin was the highlight of the vacation for my kids. We shared it with my brother and his family and the kids had a wonderful time between the loft bedroom and the short hiking trail around t
                                      …see more

                                      Price per night from

                                      $263

                                      Responds fast!
                                      avg. 2 hours 12 minutes

                                      Price per night from

                                      $263

                                      Distance approx 9.68 km from Massies Mill

                                      (6) Excellent 

                                      Certificate of Excellence

                                        15

                                        TREELOFT- in the snow drift!

                                        Virginia / Wintergreen

                                        Wintergreen house

                                        3 8 min stay varies

                                        • 3 bedrooms
                                        • sleeps 8
                                        • min stay varies
                                        • Child Friendly

                                        Certificate of Excellence

                                        Price per night from

                                        $447

                                        Responds fast!
                                        avg. 14 minutes

                                        Price per night from

                                        $447

                                        Distance approx 10.8 km from Massies Mill

                                        (1) Average 

                                          24

                                          Peaceful Roseland House w/ Loft, Deck & Mtn Views!

                                          Virginia / Wintergreen

                                          Wintergreen house

                                          4 10 min stay varies

                                          • 4 bedrooms
                                          • sleeps 10
                                          • min stay varies
                                          • Swimming pool
                                          • Ski
                                          • Child Friendly

                                          Price per night from

                                          $327

                                          Responds fast!
                                          avg. 29 minutes

                                          Price per night from

                                          $327

                                          Distance approx 9.8 km from Massies Mill

                                            25

                                            Wintergreen Studio w/ 4th of July Fireworks Views!

                                            Virginia / Wintergreen

                                            Wintergreen studio

                                            Studio 2 min stay varies

                                            • Studio
                                            • sleeps 2
                                            • min stay varies
                                            • Ski
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $98

                                            Responds fast!
                                            avg. 20 minutes

                                            Price per night from

                                            $98

                                            Distance approx 9.09 km from Massies Mill

                                            (11) Excellent 

                                              68

                                              Fit for a KING ( king size beds!)

                                              Virginia / Wintergreen

                                              Wintergreen house

                                              5 10 min stay varies

                                              • 5 bedrooms
                                              • sleeps 10
                                              • min stay varies
                                              • Swimming pool
                                              • Child Friendly
                                              “Great!” The process of reserving, paying, getting in the house and out of the house was easy and fool-proof!! The house was amazing and the location was perfect. Dawn (the contact for the house) was the most helpful and thoughtful person you could
                                              …see more

                                              Price per night from

                                              $561

                                              Responds fast!
                                              avg. 14 minutes

                                              Price per night from

                                              $561

                                              Distance approx 10.73 km from Massies Mill

                                              (2) Excellent 

                                                24

                                                Chestnut Place Mountain Lodge

                                                Virginia / Wintergreen

                                                Wintergreen house

                                                5 15 min stay varies

                                                • 5 bedrooms
                                                • sleeps 15
                                                • min stay varies
                                                • Swimming pool
                                                • Ski
                                                • Child Friendly

                                                Price per night from

                                                $630

                                                Responds fast!
                                                avg. 14 minutes

                                                Price per night from

                                                $630

                                                Distance approx 10.59 km from Massies Mill

                                                  38

                                                  '5 Peaks' Luxury Wintergreen Resort Home w/Hot Tub

                                                  Virginia / Wintergreen

                                                  Wintergreen house

                                                  3 8 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 8
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Ski
                                                  • Child Friendly

                                                  Price per night from

                                                  $275

                                                  Responds fast!
                                                  avg. 20 minutes

                                                  Price per night from

                                                  $275

                                                  Distance approx 10.71 km from Massies Mill

                                                    24

                                                    NEW! Wintergreen Condo w/Views & Shuttle to Resort

                                                    Virginia / Wintergreen

                                                    Wintergreen condo

                                                    3 8 min stay varies

                                                    • 3 bedrooms
                                                    • sleeps 8
                                                    • min stay varies
                                                    • Ski
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $161

                                                    Responds fast!
                                                    avg. 20 minutes

                                                    Price per night from

                                                    $161

                                                    Distance approx 11.09 km from Massies Mill

                                                    (1) Excellent 

                                                      32

                                                      A Cajun Chalet

                                                      Virginia / Wintergreen

                                                      Wintergreen house

                                                      4 8 min stay varies

                                                      • 4 bedrooms
                                                      • sleeps 8
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $561

                                                      Responds fast!
                                                      avg. 14 minutes

                                                      Price per night from

                                                      $561

                                                      Distance approx 10.9 km from Massies Mill

                                                      (1) Excellent 

                                                        29

                                                        Luxury Custom Home in Wintergreen Resort Area!

                                                        Virginia / Wintergreen

                                                        Wintergreen house

                                                        3 10 min stay varies

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

                                                        Price per night from

                                                        $304

                                                        Responds fast!
                                                        avg. 19 minutes

                                                        Price per night from

                                                        $304

                                                        Distance approx 10.6 km from Massies Mill

                                                        (1) Excellent 

                                                          34

                                                          Mountaintop Lodge, Wintergreen Resort

                                                          Virginia / Wintergreen

                                                          Wintergreen house

                                                          9 24 2 nights min

                                                          • 9 bedrooms
                                                          • sleeps 24
                                                          • 2 nights min
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $1,460

                                                          Price per night from

                                                          $1,460

                                                          Distance approx 9.67 km from Massies Mill

                                                          (1) Excellent 

                                                            23

                                                            NEW! Cozy Wintergreen Resort Condo w/ Pool Access!

                                                            Virginia / Wintergreen

                                                            Wintergreen condo

                                                            2 6 min stay varies

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

                                                            Price per night from

                                                            $126

                                                            Responds fast!
                                                            avg. 20 minutes

                                                            Price per night from

                                                            $126

                                                            Distance approx 10.16 km from Massies Mill

                                                              24

                                                              NEW! Modern Wintergreen Farmhouse - 1 Mi to Resort

                                                              Virginia / Wintergreen

                                                              Wintergreen condo

                                                              4 8 min stay varies

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Ski
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $287

                                                              Responds fast!
                                                              avg. 20 minutes

                                                              Price per night from

                                                              $287

                                                              Distance approx 10.63 km from Massies Mill

                                                                9

                                                                Mountain Retreat

                                                                Virginia / Wintergreen

                                                                Wintergreen house

                                                                5 8 min stay varies

                                                                • 5 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Child Friendly

                                                                Price per night from

                                                                $344

                                                                Price per night from

                                                                $344

                                                                Distance approx 11.52 km from Massies Mill

                                                                  28

                                                                  NEW! Lavish Wintergreen Home w/Hot Tub by Skiing!

                                                                  Virginia / Wintergreen

                                                                  Wintergreen house

                                                                  4 12 min stay varies

                                                                  • 4 bedrooms
                                                                  • sleeps 12
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Ski
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $346

                                                                  Responds fast!
                                                                  avg. 20 minutes

                                                                  Price per night from

                                                                  $346

                                                                  Distance approx 16.04 km from Massies Mill

                                                                    26

                                                                    ❤The Blue HummingBird❤9acre Nature's Hideaway❤Farm Country Getaway❤

                                                                    Virginia / Staunton

                                                                    Staunton house

                                                                    3 6 1 night min

                                                                    • 3 bedrooms
                                                                    • sleeps 6
                                                                    • 1 night min
                                                                    • Child Friendly
                                                                    • Air conditioning
                                                                    • Private garden

                                                                    Price per night from

                                                                    $142

                                                                    Price per night from

                                                                    $142

                                                                    Distance approx 11.27 km from Massies Mill

                                                                      26

                                                                      NEW! Wintergreen Home w/Deck & Community Amenities

                                                                      Virginia / Wintergreen

                                                                      Wintergreen house

                                                                      3 10 min stay varies

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

                                                                      Price per night from

                                                                      $281

                                                                      Responds fast!
                                                                      avg. 20 minutes

                                                                      Price per night from

                                                                      $281

                                                                      Distance approx 9.57 km from Massies Mill

                                                                        25

                                                                        Wintergreen Cabin in Quiet Location Near Slopes!

                                                                        Virginia / Wintergreen

                                                                        Wintergreen cottage

                                                                        3 6 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $178

                                                                        Responds fast!
                                                                        avg. 20 minutes

                                                                        Price per night from

                                                                        $178

                                                                        Distance approx 10.7 km from Massies Mill

                                                                        (6) Excellent 

                                                                          29

                                                                          ALMOST HEAVEN AT WINTERGREEN RESORT!

                                                                          Virginia / Wintergreen

                                                                          Wintergreen house

                                                                          4 8 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Private garden

                                                                          Price per night from

                                                                          $447

                                                                          Responds fast!
                                                                          avg. 14 minutes

                                                                          Price per night from

                                                                          $447

                                                                          Distance approx 9.61 km from Massies Mill

                                                                          (26) Excellent 

                                                                            17

                                                                            WINTERGREEN MOUNTAIN HOUSE

                                                                            Virginia / Wintergreen

                                                                            Wintergreen house

                                                                            4 8 2 nights min

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

                                                                            Price per night from

                                                                            $229

                                                                            Responds fast!
                                                                            avg. 1 hour 16 minutes

                                                                            Price per night from

                                                                            $229

                                                                            Distance approx 9.94 km from Massies Mill

                                                                            (10) Very Good 

                                                                              24

                                                                              Top of the Resort (Discounted Rates Available)

                                                                              Virginia / Wintergreen

                                                                              Wintergreen house

                                                                              6 14 2 nights min

                                                                              • 6 bedrooms
                                                                              • sleeps 14
                                                                              • 2 nights min
                                                                              • Child Friendly
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $329

                                                                              Price per night from

                                                                              $329