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15 Houses

(1) Very Good 

    24

    Just Like Heaven Carriage House

    Virginia / Winchester

    Winchester cottage

    1 2 1 night min

    • 1 bedroom
    • sleeps 2
    • 1 night min
    • Air conditioning

    Price per night from

    $144

    Price per night from

    $144

    Great rentals within 20 miles that match your search

    Distance approx 10.73 km from Winchester Show on Map

    (4) Excellent 

      90

      Charming Historic Home in Shenandoah Valley Wine Country near Skyline Drive

      Virginia / Millwood

      Millwood house

      5 14 2 nights min

      • 5 bedrooms
      • sleeps 14
      • 2 nights min
      • Child Friendly
      • Air conditioning
      • Pet Friendly

      Price per night from

      $286

      Responds fast!
      avg. 1 hour 24 minutes

      Price per night from

      $286

      Distance approx 17.51 km from Winchester

        24

        NEW! Cozy Garden-Level Apt - Walk to Charles Town!

        West Virginia / Charles Town

        Charles Town apartment

        1 2 min stay varies

        • 1 bedroom
        • sleeps 2
        • min stay varies
        • Child Friendly
        • Air conditioning

        Price per night from

        $103

        Responds fast!
        avg. 39 minutes

        Price per night from

        $103

        Distance approx 19.7 km from Winchester

          28

          Franklin Manor - Close to Front Royal and Attractions

          Virginia / Front Royal

          Front Royal house

          4 6 min stay varies

          • 4 bedrooms
          • sleeps 6
          • min stay varies
          • Child Friendly
          • Air conditioning
          • Pet Friendly

          Price per night from

          $229

          Price per night from

          $229

          Distance approx 19.66 km from Winchester

            26

            Large Modern House, VA Wine Country

            Virginia / Upperville

            Upperville house

            7 14 2 nights min

            • 7 bedrooms
            • sleeps 14
            • 2 nights min
            • Child Friendly
            • Air conditioning
            • Private garden

            Price per night from

            $228

            Price per night from

            $228

            Distance approx 19.1 km from Winchester

            (16) Very Good 

              64

              Celebration Retreat, a fun venue in Wine Country

              Virginia / Front Royal

              Front Royal house

              4 25 2 nights min

              • 4 bedrooms
              • sleeps 25
              • 2 nights min
              • Child Friendly
              • Car not necessary
              • Air conditioning
              “Very lovely and full of entertainment!!” Me and my girlfriend had wonderful time at this home. Especially, the theater was great and view from home was fantastic.

              Price per night from

              $212

              Responds fast!
              avg. 3 hours 35 minutes

              Price per night from

              $212

              Distance approx 19.57 km from Winchester

                5

                Wine Country Retreat 60 miles from DC

                Virginia / Markham

                Markham house

                4 12 2 nights min

                • 4 bedrooms
                • sleeps 12
                • 2 nights min
                • Child Friendly
                • Pet Friendly

                Price per night from

                $573

                Responds fast!
                avg. 28 minutes

                Price per night from

                $573

                Distance approx 11.28 km from Winchester Show on Map

                (11) Excellent 

                  19

                  Ruby Summit Point - Your Home at the Track

                  West Virginia / Summit Point

                  Summit Point house

                  3 6 2 nights min

                  • 3 bedrooms
                  • sleeps 6
                  • 2 nights min
                  • Air conditioning
                  • Ask about pets
                  • Private garden
                  “Convenience and Comfort at the Track” Ruby Summit Point is a great place to say with a group of friends over a track weekend. Very close to the track so no time wasted commuting to distant hotels. Very nicely upgraded kitchen and entire house. Beautif

                  Price per night from

                  $229

                  Price per night from

                  $229

                  Distance approx 18.29 km from Winchester

                    23

                    Idyllic Restored 18c cabin Blue Ridge 30ac in Wine country! Views*All Amenities.

                    Loudoun County / Bluemont

                    Bluemont house

                    2 3 7 nights min

                    • 2 bedrooms
                    • sleeps 3
                    • 7 nights min
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $102

                    Price per night from

                    $102

                    Distance approx 18.43 km from Winchester

                      24

                      Beaver Dam Lodge

                      West Virginia / Berkeley Springs

                      Berkeley Springs house

                      3 6 2 nights min

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

                      Price per night from

                      $258

                      Price per night from

                      $258

                      Distance approx 17.51 km from Winchester

                      (62) Excellent 

                      Certificate of Excellence

                        45

                        Rainbow View Cabin - Shenandoah Valley view & hottub

                        Virginia / Linden

                        Linden log cabin

                        2 4 min stay varies

                        • 2 bedrooms
                        • sleeps 4
                        • min stay varies
                        • Child Friendly
                        • Air conditioning
                        • Pet Friendly
                        “Perfect as always” Lovely anniversary weekend. Owners are amazing which makes the already well maintained and perfectly located property seem even better... Already checking my calendar for next trip!

                        Certificate of Excellence

                        Price per night from

                        $178

                        Responds fast!
                        avg. 15 minutes

                        Price per night from

                        $178

                        Distance approx 17.04 km from Winchester

                        (15) Excellent 

                        Certificate of Excellence

                          27

                          Valley Vista Cabin - Shenandoah River & Massanutten/Allegheny Mt view w/ hot tub

                          Virginia / Linden

                          Linden house

                          3 6 min stay varies

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

                          Certificate of Excellence

                          Price per night from

                          $235

                          Responds fast!
                          avg. 15 minutes

                          Price per night from

                          $235

                          Distance approx 17.77 km from Winchester

                            15

                            Private and Remodeled Historic 2 Bedroom Condo in Heart of Downtown Charles Town

                            West Virginia / Charles Town

                            Charles Town apartment

                            2 5 1 night min

                            • 2 bedrooms
                            • sleeps 5
                            • 1 night min
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $114

                            Price per night from

                            $114

                            Distance approx 17.77 km from Winchester

                              12

                              Private One Bedroom Condo in Downtown Charles Town Above Future Microbrewery

                              West Virginia / Charles Town

                              Charles Town apartment

                              1 4 1 night min

                              • 1 bedroom
                              • sleeps 4
                              • 1 night min
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $114

                              Price per night from

                              $114

                              Distance approx 16.14 km from Winchester

                                29

                                Looking for incredible comfort and amazing amenities? Penny Lane~Perfect!

                                Virginia / Lebanon Church

                                Lebanon Church townhouse

                                3 6 3 nights min

                                • 3 bedrooms
                                • sleeps 6
                                • 3 nights min
                                • Swimming pool
                                • Ask about children
                                • Air conditioning

                                Price per night from

                                $200

                                Price per night from

                                $200