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64 Houses

(3) Very Good 

    7

    Beautiful Home and Best Value at Wintergreen

    Virginia / Roseland

    Roseland townhouse

    4 8 3 nights min

    • 4 bedrooms
    • sleeps 8
    • 3 nights min
    • Child Friendly
    • Air conditioning

    Price per night from

    $429

    Price per night from

    $429

    Great rentals within 20 miles that match your search

    Distance approx 12.11 km from Roseland Show on Map

    (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

      $211

      Responds fast!
      avg. 33 minutes

      Price per night from

      $211

      Distance approx 8.25 km from Roseland

      (10) Very Good 

        28

        Peaceful Seclusion in The Blue Ridge,Pet friendly

        Virginia / Lovingston

        Lovingston log cabin

        2 6 3 nights min

        • 2 bedrooms
        • sleeps 6
        • 3 nights min
        • Nearest beach 322 mi
        • Child Friendly
        • Air conditioning
        “Absolutely perfect!” This cabin is adorable! The setting is completely secluded and was the perfect spot for my family to stay as I graduated from Liberty University this past weekend. My boys were able to run and be loud and loved cooking their own

        Price per night from

        $170

        Price per night from

        $170

        Distance approx 17.6 km from Roseland

        (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

          $183

          Responds fast!
          avg. 2 hours 57 minutes

          Price per night from

          $183

          Distance approx 15.32 km from Roseland

            13

            The Mountain Outpost

            Virginia / Vesuvius

            Vesuvius house

            3 6 2 nights min

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

            Price per night from

            $200

            Responds fast!
            avg. 2 hours 29 minutes

            Price per night from

            $200

            Distance approx 12.75 km from Roseland

            (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

              $326

              Responds fast!
              avg. 40 minutes

              Price per night from

              $326

              Distance approx 12 km from Roseland

              (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!

                Price per night from

                $171

                Responds fast!
                avg. 2 hours 12 minutes

                Price per night from

                $171

                Distance approx 5.82 km from Roseland

                  21

                  Lovingston Get-Away

                  Virginia / Lovingston

                  Lovingston apartment

                  2 4 2 nights min

                  • 2 bedrooms
                  • sleeps 4
                  • 2 nights min
                  • Swimming pool
                  • Air conditioning
                  • Private garden

                  Price per night from

                  $115

                  Price per night from

                  $115

                  Distance approx 10.5 km from Roseland

                  (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

                    Price per night from

                    $315

                    Responds fast!
                    avg. 1 hour 19 minutes

                    Price per night from

                    $315

                    Distance approx 12.13 km from Roseland Show on Map

                    (3) Very Good 

                      16

                      Down On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities

                      Virginia / Wintergreen

                      Wintergreen condo

                      2 6 1 night min

                      • 2 bedrooms
                      • sleeps 6
                      • 1 night min
                      • Swimming pool
                      • Ski
                      • Child Friendly

                      Price per night from

                      $115

                      Responds fast!
                      avg. 3 hours 1 minutes

                      Price per night from

                      $115

                      Distance approx 12.79 km from Roseland

                      (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

                        $452

                        Price per night from

                        $452

                        Distance approx 10.5 km from Roseland

                        (5) Excellent 

                          26

                          Romantic, Pet-Friendly Cabin in Blue Ridge Mountains - Barnwood

                          Virginia / Tyro

                          Tyro log cabin

                          1 4 2 nights min

                          • 1 bedroom
                          • sleeps 4
                          • 2 nights min
                          • Nearest beach 3 mi
                          • Swimming pool
                          • Child Friendly
                          “Peaceful and Beautiful” My husband, 8 month old son, and I took our best friend for a weekend of relaxation before she left to go into some difficult and strenuous work for the summer. It was the perfect place for us all to go. The house was adorable

                          Price per night from

                          $148

                          Responds fast!
                          avg. 2 hours 12 minutes

                          Price per night from

                          $148

                          Distance approx 12.04 km from Roseland Show on Map

                          (1) Excellent 

                            10

                            Cozy and Clean Resort Condo - New Ownership and listed for the first time!

                            Virginia / Wintergreen

                            Wintergreen condo

                            1 4 2 nights min

                            • 1 bedroom
                            • sleeps 4
                            • 2 nights min
                            • Nearest beach 265 mi
                            • Ski
                            • Child Friendly

                            Price per night from

                            $102

                            Price per night from

                            $102

                            Distance approx 11.69 km from Roseland

                              44

                              New Log Home, Private, Beautiful location, River Access, Walk/Hike/Bike/Kayak

                              Virginia / Faber

                              Faber house

                              3 6 2 nights min

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

                              Price per night from

                              $178

                              Price per night from

                              $178

                              Distance approx 15.91 km from Roseland

                                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

                                $571

                                Responds fast!
                                avg. 10 minutes

                                Price per night from

                                $571

                                Distance approx 11.16 km from Roseland

                                  22

                                  Dogwood Haven

                                  Virginia / Wintergreen

                                  Wintergreen apartment

                                  2 4 2 nights min

                                  • 2 bedrooms
                                  • sleeps 4
                                  • 2 nights min
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $172

                                  Responds fast!
                                  avg. 1 hour 4 minutes

                                  Price per night from

                                  $172

                                  Distance approx 3.17 km from Roseland

                                  (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 54 minutes

                                    Price per night from

                                    $172

                                    Distance approx 11.77 km from Roseland Show on Map

                                    (10) Excellent 

                                      41

                                      CRAZY AMAZING get-a-way! (Crazy, in a GOOD way)

                                      Virginia / Wintergreen

                                      Wintergreen house

                                      5 13 min stay varies

                                      • 5 bedrooms
                                      • sleeps 13
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $675

                                      Responds fast!
                                      avg. 12 minutes

                                      Price per night from

                                      $675

                                      Distance approx 11.9 km from Roseland

                                      (9) Excellent 

                                        22

                                        Pet Friendly 2BR Cabin in Blue Ridge Mtns of VA

                                        Virginia / Waynesboro

                                        Waynesboro log cabin

                                        2 6 2 nights min

                                        • 2 bedrooms
                                        • sleeps 6
                                        • 2 nights min
                                        • Nearest beach 3 mi
                                        • Swimming pool
                                        • Child Friendly
                                        “The best vacation ever!” I hesitate to rave about Cabin Mountainwood for fear that it won't be available for our next visit. But I must be truthful... My husband, our dog Jenny and I had the most wonderful, carefree 5 days of our lives. We fished.

                                        Price per night from

                                        $148

                                        Responds fast!
                                        avg. 2 hours 12 minutes

                                        Price per night from

                                        $148

                                        Distance approx 18.02 km from Roseland

                                        (9) Excellent 

                                        Certificate of Excellence

                                          27

                                          H'Owl at the Moon Farm

                                          Virginia / Charlottesville

                                          Charlottesville log cabin

                                          2 4 min stay varies

                                          • 2 bedrooms
                                          • sleeps 4
                                          • min stay varies
                                          • Child Friendly
                                          • Air conditioning
                                          • Pet Friendly

                                          Certificate of Excellence

                                          Price per night from

                                          $190

                                          Responds fast!
                                          avg. 1 hour 42 minutes

                                          Price per night from

                                          $190

                                          Distance approx 12.27 km from Roseland

                                          (25) Very Good 

                                            24

                                            Cabin at Wintergreen - VA Mt. Resort Luxury Rental

                                            Virginia / Wintergreen

                                            Wintergreen house

                                            5 10 2 nights min

                                            • 5 bedrooms
                                            • sleeps 10
                                            • 2 nights min
                                            • Ski
                                            • Child Friendly
                                            “All we needed in a cabin for a great weekend getaway.” This place was great! I took a group of young adults from my church, and they were all impressed with the house. They kept asking me, "Where did you find this place?" The cabin feels very rustic a

                                            Price per night from

                                            $400

                                            Price per night from

                                            $400

                                            Distance approx 8.35 km from Roseland

                                            (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

                                              $286

                                              Price per night from

                                              $286

                                              Distance approx 10.34 km from Roseland

                                              (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

                                                Price per night from

                                                $561

                                                Responds fast!
                                                avg. 12 minutes

                                                Price per night from

                                                $561

                                                Distance approx 12.12 km from Roseland

                                                  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

                                                  $223

                                                  Price per night from

                                                  $223

                                                  Distance approx 11.89 km from Roseland

                                                  (4) Very Good 

                                                    23

                                                    Pet-Friendly Secluded Mountain Cabin by Pool - Rockwood

                                                    Virginia / Staunton

                                                    Staunton log cabin

                                                    2 6 2 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 2 nights min
                                                    • Nearest beach 3 mi
                                                    • Swimming pool
                                                    • Child Friendly
                                                    “Great place to stay close to Blue Ridge Parkway” This is a nice quiet place to stay that is just a couple minutes down the hill from the Blue Ridge Parkway.

                                                    Price per night from

                                                    $148

                                                    Responds fast!
                                                    avg. 2 hours 12 minutes

                                                    Price per night from

                                                    $148

                                                    Distance approx 12.57 km from Roseland

                                                    (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

                                                      $629

                                                      Responds fast!
                                                      avg. 12 minutes

                                                      Price per night from

                                                      $629

                                                      Distance approx 12.13 km from Roseland Show on Map

                                                      (4) Very Good 

                                                        15

                                                        Up-On 18th! Walk to Golf Clubhouse, Spa, Pool, Membership Access to Facilities

                                                        Virginia / Wintergreen

                                                        Wintergreen condo

                                                        2 6 1 night min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 1 night min
                                                        • Swimming pool
                                                        • Ski
                                                        • Child Friendly

                                                        Price per night from

                                                        $115

                                                        Responds fast!
                                                        avg. 3 hours 1 minutes

                                                        Price per night from

                                                        $115

                                                        Distance approx 15.76 km from Roseland

                                                          8

                                                          Luxury Yurt in the Blue Ridge Mountains of Virginia Near Wintergreen

                                                          Virginia / Afton

                                                          Afton yurt

                                                          1 5 2 nights min

                                                          • 1 bedroom
                                                          • sleeps 5
                                                          • 2 nights min
                                                          • Beach / lakeside relaxation

                                                          Price per night from

                                                          $172

                                                          Price per night from

                                                          $172

                                                          Distance approx 10.52 km from Roseland

                                                          (7) Excellent 

                                                            28

                                                            Civil War Cabin Built by Confederate Soldier in Blue Ridge Mountains

                                                            Virginia / Charlottesville

                                                            Charlottesville log cabin

                                                            1 4 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • 2 nights min
                                                            • Nearest beach 3 mi
                                                            • Swimming pool
                                                            • Child Friendly
                                                            “Serene cabin near running creek” Dear Stan, We had a wonderful stay last month in the logwood cabin, that dates back to the Civil War. It was a very unique cabin with a homely, quaint feel. There was a lovely little fireplace and the cabin felt ver

                                                            Price per night from

                                                            $182

                                                            Responds fast!
                                                            avg. 2 hours 12 minutes

                                                            Price per night from

                                                            $182

                                                            Distance approx 11.85 km from Roseland

                                                              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. 10 minutes

                                                              Price per night from

                                                              $241

                                                              Distance approx 11.5 km from Roseland Show on Map

                                                                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

                                                                $160

                                                                Responds fast!
                                                                avg. 10 minutes

                                                                Price per night from

                                                                $160

                                                                Distance approx 11.75 km from Roseland

                                                                  32

                                                                  NEW! Chic Cabin w/Deck in Wintergreen Resort!

                                                                  Virginia / Wintergreen

                                                                  Wintergreen cottage

                                                                  3 6 min stay varies

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

                                                                  Price per night from

                                                                  $206

                                                                  Responds fast!
                                                                  avg. 10 minutes

                                                                  Price per night from

                                                                  $206

                                                                  Distance approx 12.07 km from Roseland Show on Map

                                                                    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

                                                                    $286

                                                                    Responds fast!
                                                                    avg. 10 minutes

                                                                    Price per night from

                                                                    $286

                                                                    Distance approx 10.88 km from Roseland

                                                                    (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

                                                                      $223

                                                                      Price per night from

                                                                      $223

                                                                      Distance approx 11.52 km from Roseland Show on Map

                                                                      (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. 10 minutes

                                                                        Price per night from

                                                                        $126

                                                                        Distance approx 13.33 km from Roseland

                                                                          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

                                                                          $361

                                                                          Responds fast!
                                                                          avg. 10 minutes

                                                                          Price per night from

                                                                          $361

                                                                          Distance approx 11.93 km from Roseland

                                                                            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. 10 minutes

                                                                            Price per night from

                                                                            $275

                                                                            Distance approx 11.33 km from Roseland

                                                                              25

                                                                              Quiet Cabin Near Hiking Trails and Mountain Inn!

                                                                              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. 10 minutes

                                                                              Price per night from

                                                                              $178