Vacation Rentals & Villas in Winter Park

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834 villas

    24

    Newly Remodeled Slopeside Townhouse

    Grand County / Winter Park

    Winter Park townhouse

    3 8 3 nights min

    • 3 bedrooms
    • sleeps 8
    • 3 nights min
    • Ski
    • Child Friendly

    Price per night from

    $567

    Price per night from

    $567

      38

      Lakota Trailside 613

      Grand County / Winter Park

      Winter Park house

      3 8 min stay varies

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

      Price per night from

      $22

      Price per night from

      $22

      (1) Excellent 

        24

        3BR Winter Park Home w/Private Hot Tub & Mtn Views

        Grand County / Winter Park

        Winter Park house

        3 7 min stay varies

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

        Price per night from

        $235

        Responds fast!
        avg. 19 minutes

        Price per night from

        $235

          24

          Riverside 2BR Winter Park Condo w/Hot Tub Access!

          Grand County / Winter Park

          Winter Park apartment

          2 7 min stay varies

          • 2 bedrooms
          • sleeps 7
          • min stay varies
          • Ski
          • Child Friendly
          • Pet Friendly

          Price per night from

          $132

          Responds fast!
          avg. 37 minutes

          Price per night from

          $132

            12

            Timbers 6-1

            Grand County / Winter Park

            Winter Park condo

            3 8 min stay varies

            • 3 bedrooms
            • sleeps 8
            • min stay varies
            • Child Friendly
            • Car not necessary
            • Pet Friendly

            Price per night from

            $252

            Responds fast!
            avg. 3 hours 11 minutes

            Price per night from

            $252

            (6) Very Good 

              32

              Zephyr Mountain Lodge 2404

              Grand County / Winter Park

              Winter Park house

              2 8 min stay varies

              • 2 bedrooms
              • sleeps 8
              • min stay varies
              • Child Friendly
              “Awesome, great place to stay.” Awesome, my only complaint would be is that it was a little to hot inside the condo, other than that it was great. Spacious and peaceful.
              …see more

              Price per night from

              $17

              Price per night from

              $17

                26

                Ski-In/Ski-Out Winter Park Condo w/Resort Hot Tubs

                Grand County / Winter Park

                Winter Park apartment

                1 4 min stay varies

                • 1 bedroom
                • sleeps 4
                • min stay varies
                • Ski
                • Child Friendly

                Price per night from

                $98

                Responds fast!
                avg. 47 minutes

                Price per night from

                $98

                (3) Average 

                  29

                  Mary Jane Chalet

                  Grand County / Winter Park

                  Winter Park house

                  6 10 min stay varies

                  • 6 bedrooms
                  • sleeps 10
                  • min stay varies
                  • Ask about children
                  • Pet Friendly

                  Price per night from

                  $365

                  Responds fast!
                  avg. 3 hours 5 minutes

                  Price per night from

                  $365

                    24

                    Winter Park Condo w/Views & Ski-In/Ski-Out Access!

                    Grand County / Winter Park

                    Winter Park apartment

                    1 5 min stay varies

                    • 1 bedroom
                    • sleeps 5
                    • min stay varies
                    • Swimming pool
                    • Ski
                    • Child Friendly

                    Price per night from

                    $98

                    Responds fast!
                    avg. 37 minutes

                    Price per night from

                    $98

                      24

                      Winter Park Condo w/ Amenities - Mins to Slopes!

                      Grand County / Winter Park

                      Winter Park apartment

                      1 4 min stay varies

                      • 1 bedroom
                      • sleeps 4
                      • min stay varies
                      • Swimming pool
                      • Ski
                      • Child Friendly

                      Price per night from

                      $109

                      Responds fast!
                      avg. 33 minutes

                      Price per night from

                      $109

                        20

                        Snowblaze Condominiums B22

                        Grand County / Winter Park

                        Winter Park apartment

                        2 6 min stay varies

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

                        Price per night from

                        $152

                        Responds fast!
                        avg. 3 hours 5 minutes

                        Price per night from

                        $152

                          29

                          Winter Park Home w/Ski Hill Views, Sauna & Hot Tub

                          Grand County / Winter Park

                          Winter Park house

                          5 12 min stay varies

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

                          Price per night from

                          $458

                          Responds fast!
                          avg. 33 minutes

                          Price per night from

                          $458

                          (1) Excellent 

                            18

                            Bright, Updated Top Floor Unit With Great Views

                            Grand County / Winter Park

                            Winter Park condo

                            2 6 min stay varies

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

                            Price per night from

                            $201

                            Price per night from

                            $201

                            (4) Excellent 

                              34

                              Dreamcatcher 7B Rental

                              Grand County / Winter Park

                              Winter Park house

                              5 11 min stay varies

                              • 5 bedrooms
                              • sleeps 11
                              • min stay varies
                              • Child Friendly
                              “Great Experience, no-hassle rental” This is a nice rental in the Lakota area just outside winter park. Everything was great. Only minor issue is we couldn't figure-out whether a shuttle to winter park was available. Drove to Mary Jane free parking.
                              …see more

                              Price per night from

                              $444

                              Responds fast!
                              avg. 3 hours 5 minutes

                              Price per night from

                              $444

                                31

                                Vasquez Run B201

                                Grand County / Winter Park

                                Winter Park house

                                2 8 min stay varies

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

                                Price per night from

                                $167

                                Responds fast!
                                avg. 3 hours 5 minutes

                                Price per night from

                                $167

                                (1) Excellent 

                                  38

                                  Snowblaze C24

                                  Grand County / Winter Park

                                  Winter Park house

                                  2 7 min stay varies

                                  • 2 bedrooms
                                  • sleeps 7
                                  • min stay varies
                                  • Swimming pool
                                  • Child Friendly

                                  Price per night from

                                  $17

                                  Price per night from

                                  $17

                                  (3) Very Good 

                                    29

                                    Base Village Loft 109

                                    Grand County / Winter Park

                                    Winter Park house

                                    3 10 min stay varies

                                    • 3 bedrooms
                                    • sleeps 10
                                    • min stay varies
                                    • Child Friendly
                                    “Wonderful, accessible Condo at Winter Park!” We really enjoyed our stay at this lovely condominium. It was a perfect location for us because it was ski in and out. There were two people who were not able to ski everyday, but they did not feel isolated
                                    …see more

                                    Price per night from

                                    $22

                                    Price per night from

                                    $22

                                      34

                                      Two Brothers Cabin

                                      Grand County / Winter Park

                                      Winter Park house

                                      5 18 min stay varies

                                      • 5 bedrooms
                                      • sleeps 18
                                      • min stay varies
                                      • Child Friendly

                                      Price per night from

                                      $32

                                      Price per night from

                                      $32

                                        24

                                        Cozy Winter Park Townhome w/ Hot Tub & Fireplace!

                                        Grand County / Winter Park

                                        Winter Park house

                                        4 10 min stay varies

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

                                        Price per night from

                                        $180

                                        Responds fast!
                                        avg. 8 minutes

                                        Price per night from

                                        $180

                                        (16) Very Good 

                                          32

                                          Telemark 698

                                          Grand County / Winter Park

                                          Winter Park house

                                          3 8 min stay varies

                                          • 3 bedrooms
                                          • sleeps 8
                                          • min stay varies
                                          • Child Friendly
                                          “Great Place” Beautiful condo. Great location right on bus route. Big rooms and very comfortable beds and nice Kitchen and spacious living area
                                          …see more

                                          Price per night from

                                          $22

                                          Price per night from

                                          $22

                                            24

                                            Inviting Winter Park Condo w/ Shuttle & Mtn Views!

                                            Grand County / Winter Park

                                            Winter Park apartment

                                            3 8 min stay varies

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

                                            Price per night from

                                            $189

                                            Responds fast!
                                            avg. 33 minutes

                                            Price per night from

                                            $189

                                            (1) Excellent 

                                              34

                                              Ponderosa Penthouse

                                              Grand County / Winter Park

                                              Winter Park apartment

                                              3 8 min stay varies

                                              • 3 bedrooms
                                              • sleeps 8
                                              • min stay varies
                                              • Ask about children

                                              Price per night from

                                              $276

                                              Responds fast!
                                              avg. 3 hours 5 minutes

                                              Price per night from

                                              $276

                                                24

                                                Large Luxurious Home,Wooded,Close town Slps16-24

                                                Grand County / Winter Park

                                                Winter Park house

                                                6 24 min stay varies

                                                • 6 bedrooms
                                                • sleeps 24
                                                • min stay varies
                                                • Child Friendly
                                                • Car not necessary
                                                • Pet Friendly

                                                Price per night from

                                                $510

                                                Responds fast!
                                                avg. 2 hours 43 minutes

                                                Price per night from

                                                $510

                                                  24

                                                  Winter Park Condo w/Amenities - 4 Mi. to Ski Lifts

                                                  Grand County / Winter Park

                                                  Winter Park apartment

                                                  1 4 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 4
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Ski
                                                  • Child Friendly

                                                  Price per night from

                                                  $109

                                                  Responds fast!
                                                  avg. 33 minutes

                                                  Price per night from

                                                  $109

                                                  (1) Excellent 

                                                    27

                                                    Beautiful Mountain House - Luxury in a Rustic Mountain Setting

                                                    Grand County / Winter Park

                                                    Winter Park house

                                                    4 14 min stay varies

                                                    • 4 bedrooms
                                                    • sleeps 14
                                                    • min stay varies
                                                    • Child Friendly
                                                    • Pet Friendly
                                                    “Reunion Weekend Getaway” We loved staying in this beautiful mountain home for a Law School Reunion Weekend Getaway with many friends! The location is picturesque and the house well-stocked, clean, comfortable, luxurious, and now home to a great memory
                                                    …see more

                                                    Price per night from

                                                    $447

                                                    Responds fast!
                                                    avg. 2 hours 43 minutes

                                                    Price per night from

                                                    $447

                                                      31

                                                      Winter Park Condo Only 2 Miles from Ski Lifts!

                                                      Grand County / Winter Park

                                                      Winter Park apartment

                                                      1 4 min stay varies

                                                      • 1 bedroom
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Ski
                                                      • Child Friendly

                                                      Price per night from

                                                      $114

                                                      Responds fast!
                                                      avg. 47 minutes

                                                      Price per night from

                                                      $114

                                                        39

                                                        Lakota Northwoods 305

                                                        Grand County / Winter Park

                                                        Winter Park house

                                                        3 12 min stay varies

                                                        • 3 bedrooms
                                                        • sleeps 12
                                                        • min stay varies
                                                        • Child Friendly

                                                        Price per night from

                                                        $22

                                                        Price per night from

                                                        $22

                                                        (4) Very Good 

                                                          14

                                                          Winter Park CO from $65.00 per Ski Season night !!

                                                          Grand County / Winter Park

                                                          Winter Park villa

                                                          4 min stay varies

                                                          • sleeps 4
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Car not necessary

                                                          Price per night from

                                                          $58

                                                          Responds fast!
                                                          avg. 2 hours 24 minutes

                                                          Price per night from

                                                          $58

                                                            24

                                                            NEW! Winter Park Studio w/Hot Tub - Walk to Lifts!

                                                            Grand County / Winter Park

                                                            Winter Park studio

                                                            Studio 4 min stay varies

                                                            • Studio
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Ski
                                                            • Child Friendly

                                                            Price per night from

                                                            $98

                                                            Responds fast!
                                                            avg. 33 minutes

                                                            Price per night from

                                                            $98

                                                            (1) Very Good 

                                                              25

                                                              NEW! Downtown Winter Park Condo w/ Balcony!

                                                              Grand County / Winter Park

                                                              Winter Park apartment

                                                              2 7 min stay varies

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

                                                              Price per night from

                                                              $144

                                                              Responds fast!
                                                              avg. 52 minutes

                                                              Price per night from

                                                              $144

                                                                34

                                                                Trailhead Lodges 822

                                                                Grand County / Winter Park

                                                                Winter Park condo

                                                                2 8 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $17

                                                                Price per night from

                                                                $17

                                                                  32

                                                                  Base Village Loft 104

                                                                  Grand County / Winter Park

                                                                  Winter Park house

                                                                  3 8 min stay varies

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

                                                                  Price per night from

                                                                  $22

                                                                  Price per night from

                                                                  $22

                                                                  (1) Excellent 

                                                                    6

                                                                    Beautifully renovated condo!!

                                                                    Grand County / Winter Park

                                                                    Winter Park condo

                                                                    1 4 2 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 4
                                                                    • 2 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Ski
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $121

                                                                    Price per night from

                                                                    $121

                                                                      30

                                                                      Zephyr Mountain Lodge 1318

                                                                      Grand County / Winter Park

                                                                      Winter Park house

                                                                      2 6 min stay varies

                                                                      • 2 bedrooms
                                                                      • sleeps 6
                                                                      • min stay varies
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $17

                                                                      Price per night from

                                                                      $17

                                                                      (27) Very Good 

                                                                        34

                                                                        Zephyr Mountain Lodge 1601

                                                                        Grand County / Winter Park

                                                                        Winter Park house

                                                                        2 6 min stay varies

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Child Friendly
                                                                        “A true ski in ski out condo!” The room satisfied our needs. We loved being able to cook our own meals in our own time frame. Most of the common utensils were provided including common spices. The only downside was the maintenance of the building. One
                                                                        …see more

                                                                        Price per night from

                                                                        $17

                                                                        Price per night from

                                                                        $17

                                                                        (1) Very Good 

                                                                          32

                                                                          Iron Horse Resort 3094

                                                                          Grand County / Winter Park

                                                                          Winter Park apartment

                                                                          2 8 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $260

                                                                          Responds fast!
                                                                          avg. 3 hours 5 minutes

                                                                          Price per night from

                                                                          $260

                                                                          (12) Very Good 

                                                                            36

                                                                            Zephyr Mountain Lodge 2307

                                                                            Grand County / Winter Park

                                                                            Winter Park house

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Child Friendly
                                                                            “A great family vacation experience” This was our first ski trip and we loved this property! Check in was easy, staff was friendly and helpful, the home was clean and had everything we needed, and the location was perfect. Ski lifts were just outside,
                                                                            …see more

                                                                            Price per night from

                                                                            $17

                                                                            Price per night from

                                                                            $17

                                                                            (6) Very Good 

                                                                              39

                                                                              Zephyr Mountain Lodge 1520

                                                                              Grand County / Winter Park

                                                                              Winter Park house

                                                                              3 8 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 8
                                                                              • min stay varies
                                                                              • Child Friendly
                                                                              “Excellent Mountain Spot” First let me say that we are already planning our next trip back to the Zephyr Lodge. The condo was outstanding. The staff at Winter Park Resort were the most friendly that I have ever been around, and I live in a vacation a
                                                                              …see more

                                                                              Price per night from

                                                                              $22

                                                                              Price per night from

                                                                              $22

                                                                              About Winter Park

                                                                              There are few places in the world that can rival Winter Park, Colorado, for beauty and pristine nature. For skiers, snowboarders, and sight seeking travelers alike, the marvel of the Rockies can become your backyard while staying in your very own vacation home. Pursue outdoor adventures by day and step back inside your rental home at night, the perfect place to enjoy a chili cookout with friends and family. Vacation homes in Winter Park can provide a refreshing alternative to the constrictions and hassles of hotels.

                                                                              Offering only the very best, Winter Park's world-class ski slopes attract skiers of all skill levels. Voted the number one resort by in-state skiers, Winter Park Ski Resort is known as "Colorado's Favorite," and claims an average annual snowfall of 350 inches per year. Winter Park offers activities not just for winter, but for all seasons. Though skiing may feel like the pinnacle of all Winter Park, Colorado, activity, there is an incredible amount to see and do here all year long. For example, you can hike beautiful mountain trails, bike ride through the city, or horseback ride along the water.

                                                                              Here are a few additional suggestions as you plan your trip:

                                                                              • Experience the Winter Park Music Festival: This annual event offers a summer concert season that begins in the middle of July. Mix it up with the JVC Jazz Festival, offering a blend of funk, soul, and of course, jazz.
                                                                              • See a live theater production: Live performances and theatrical productions take place every summer from mid-June to August.
                                                                              • Take part in the race: Downhill skiing is not the only option for Colorado travelers. The Grand Lake, 25 miles from Winter Park, is home to fabulous cross country skiing and a Classic Cross Country Skiing Race in March.
                                                                              • See Winter Park from above: Take flight in a Great Adventure Balloon Tour, located just one hour from Denver, and view the Rocky Mountain Park in an unforgettable way.
                                                                              • Meet world class dog sledding teams: During Winter Park's annual dog sled races, teams of dogs pull sleds along an 8 mile track. These races are popular with spectators because of the opportunity to interact with both the dogs and the mushers.
                                                                              • Hike the trails: Go hiking, biking, or Winter Park snowmobiling through the Apache National Forest. Straddling the continental divide in north central Colorado, the forest represents the quiet side of Rocky Mountain National Park.

                                                                              Snowboard and ski Winter Park's slopes during the cold season, and come back in the spring to see the mountains bloom with wildflowers. No matter when you choose to schedule your visit, experience the beauty of the Rocky Mountains from your own private luxury vacation rental. Rent a trendy condo close to the shopping and nightlife downtown, or find a secluded lakeside cabin with all the amenities you and your family need for the perfect vacation adventure. While you're visiting Winter Park, you may also want to explore beautiful nearby mountain destinations like Vail and Telluride.