Vacation Rentals & Houses in Wintergreen

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89 houses

    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. 19 minutes

    Price per night from

    $241

    (1) Excellent 

      39

      Central Wintergreen Home - 70 Steps to Ski Slopes!

      Virginia / Wintergreen

      Wintergreen house

      5 12 min stay varies

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

      Price per night from

      $397

      Responds fast!
      avg. 11 minutes

      Price per night from

      $397

        23

        Ski-in/Ski-out Wintergreen House 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

        $218

        Responds fast!
        avg. 11 minutes

        Price per night from

        $218

        (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

          (4) Very Good 

            16

            Tyro Slope-Side House Ski In/Out Yr Rnd Views w/AC

            Virginia / Wintergreen

            Wintergreen house

            3 8 min stay varies

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

            Price per night from

            $195

            Price per night from

            $195

            (3) Very Good 

              16

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

              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

              $115

              Price per night from

              $115

              (4) Excellent 

                19

                Pet Friendly Virginia Blue Ridge Mountain Cabin Rental-Foxwood

                Virginia / Wintergreen

                Wintergreen house

                3 8 2 nights min

                • 3 bedrooms
                • sleeps 8
                • 2 nights min
                • Nearest beach 3 mi
                • Swimming pool
                • Child Friendly
                “Great mountain getaway!” Conveneintly located near Wintergreen Resort, this is an awesome way to enjoy snowboarding and sking. The cabins are quaint and cozy and the owners are very nice. Especially their Jack Russell Toby! He visits every cabin eve
                …see more

                Price per night from

                $171

                Responds fast!
                avg. 2 hours 12 minutes

                Price per night from

                $171

                (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

                    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. 13 minutes

                    Price per night from

                    $161

                    (32) Excellent 

                    Certificate of Excellence

                      11

                      Wintergreen - Slope Side w/ Resort Pass

                      Virginia / Wintergreen

                      Wintergreen condo

                      2 4 2 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 2 nights min
                      • Swimming pool
                      • Ski
                      • Child Friendly
                      “Beautiful views, clean and comfortable condo.” We loved our stay at this condo. The view from the back deck was beautiful. We enjoyed a bit of hiking, the Zip-line, nearby Monoccan lake, family time, cooking in, and eating at area restaurants. Would c
                      …see more

                      Certificate of Excellence

                      Price per night from

                      $109

                      Responds fast!
                      avg. 1 hour 43 minutes

                      Price per night from

                      $109

                      (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. 13 minutes

                        Price per night from

                        $212

                        (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

                          (3) Very Good 

                            19

                            2BR Walkout Condo Private and Cozy!

                            Virginia / Wintergreen

                            Wintergreen apartment

                            2 5 2 nights min

                            • 2 bedrooms
                            • sleeps 5
                            • 2 nights min
                            • Swimming pool
                            • Ski
                            • Child Friendly

                            Price per night from

                            $126

                            Responds fast!
                            avg. 1 hour 13 minutes

                            Price per night from

                            $126

                              26

                              22 Tyro: Family Ski-In/Ski-Out Mountain Lodge on Upper Tyro Slope at Wintergreen

                              Virginia / Wintergreen

                              Wintergreen house

                              4 10 3 nights min

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

                              Price per night from

                              $573

                              Responds fast!
                              avg. 3 hours 8 minutes

                              Price per night from

                              $573

                              (4) Very Good 

                                15

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

                                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

                                $115

                                Price per night from

                                $115

                                (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

                                  (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
                                    …see more

                                    Price per night from

                                    $400

                                    Price per night from

                                    $400

                                      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. 11 minutes

                                      Price per night from

                                      $247

                                        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 19 minutes

                                        Price per night from

                                        $172

                                        (17) Excellent 

                                        Certificate of Excellence

                                          20

                                          The Bear Dance Cabin at Wintergreen

                                          Virginia / Wintergreen

                                          Wintergreen log cabin

                                          3 6 2 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 2 nights min
                                          • Swimming pool
                                          • Child Friendly
                                          • Air conditioning
                                          “Very nice accomidations, close to resort & slopes” The cabin is adorable & cozy. Even though it has a cabin feel, the bathrooms and kitchen are very nice and you don't feel like you're "roughing it" at all. The place a newer build, so it feels very cl
                                          …see more

                                          Certificate of Excellence

                                          Price per night from

                                          $201

                                          Responds fast!
                                          avg. 1 hour 33 minutes

                                          Price per night from

                                          $201

                                            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. 11 minutes

                                            Price per night from

                                            $98

                                            (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

                                              (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

                                                (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

                                                  (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

                                                    (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

                                                        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. 19 minutes

                                                        Price per night from

                                                        $275

                                                        (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

                                                          (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

                                                            $676

                                                            Responds fast!
                                                            avg. 14 minutes

                                                            Price per night from

                                                            $676

                                                            (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

                                                              (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

                                                                  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. 13 minutes

                                                                  Price per night from

                                                                  $161

                                                                    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. 19 minutes

                                                                    Price per night from

                                                                    $287

                                                                    (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. 11 minutes

                                                                      Price per night from

                                                                      $126

                                                                        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. 12 minutes

                                                                        Price per night from

                                                                        $346

                                                                          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. 11 minutes

                                                                          Price per night from

                                                                          $281

                                                                            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. 36 minutes

                                                                            Price per night from

                                                                            $178

                                                                              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

                                                                              $207

                                                                              Price per night from

                                                                              $207

                                                                              About Wintergreen

                                                                              Wintergreen, Virginia is busy all year round – there's plenty to do! You can try golfing, skiing, mountain climbing, hiking, biking and pretty much anything else you can think of.

                                                                              You'll find this idyllic spot on the eastern side of the Blue Ridge Mountains, and be amazed at the spectacular views from your very own Wintergreen vacation rental – get searching on FlipKey, today!

                                                                              About Wintergreen, Virginia

                                                                              The area around Wintergreen was once populated by the Tuscarora Indians who lived near the Rockfish and James rivers. The Rockfish River Valley has some spectacular scenery and is well worth visiting.

                                                                              Nearby Jamestown was the first permanent European settlement in the USA, founded by the British in 1607. Because of this, Wintergreen has lots of history to explore – try heading to one of the museums to find out more!

                                                                              The food in Wintergreen is a mix of American and European (mainly Italian and French). You can eat a hearty steak, or more delicate seafood and fish. There's something for everyone, including vegans and vegetarians.

                                                                              The area is also known for brewing delicious craft beers – some of the breweries have been going since colonial times. Try some during your stay.

                                                                              What to do

                                                                              At the Wintergreen Resort, there are two golf courses for enthusiasts, Devil's Knob and Stoney Creek. They're a great day out.

                                                                              If you like walking, go along the Rockfish Valley Loop Trail system, and visit Spruce Creek Park. If you want something a bit more challenging, head up to the Appalachian Trail.

                                                                              In winter you can go skiing, snowboarding and skate. But pack your thermals, as it can get a bit chilly.

                                                                              Visit Williamsburg and see how people lived there in previous centuries. The town is a living history museum and is full of beautifully restored 17th and 18th century buildings.

                                                                              The history of Virginia is closely linked to the Civil War. Visit the Appomattox court house, where General Robert E. Lee formally surrendered to General Ulysses S. Grant.

                                                                              Go to Bold Rock and sample the delicious ciders. You get an amazing view over Wintergreen, and there's lots of space where dogs and kids can run free.

                                                                              Lyndhurst, Virginia, is home to Humpback Rocks Visitor Center and Mountain Farm. Go to the top of Humpback Rocks and take in the majestic view.

                                                                              Top Wintergreen travel tips

                                                                              The easiest way of getting to Wintergreen is by car. You can fly to Charlottesville Albemarle airport, or to Dulles International Airport (IAD) and take a bus or shuttle service. Rent a car at the airport and drive to Wintergreen.

                                                                              If you love nature's colors, go to Wintergreen in fall. Before you go, check the foliage report from the Department of Forestry. Crabtree Falls, on the Blue Ridge Parkway, is a wonderful place for a picnic.

                                                                              Pick your own apples and pumpkins and buy butternut squash, cashews sweet potatoes and freshly pressed cider during your stay.

                                                                              Don't leave the area without visiting Devils Backbone to sample the micro-brews.

                                                                              Whenever you go to Wintergreen, Virginia, you’ll find plenty of activities to try. You can visit the Civil War battlefields, walk the Rockfish Valley Loop Trail, or go to see the historic buildings of Virginia.

                                                                              Check out Wintergreen vacation rentals here on FlipKey and book your perfect stay.