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319 Houses

(18) Excellent 

    36

    Woodstock VT Village Log Home Apartment WINTER WONDERLAND

    Vermont / Woodstock

    Woodstock apartment

    1 4 min stay varies

    • 1 bedroom
    • sleeps 4
    • min stay varies
    • Child Friendly
    • Air conditioning
    “A great way to see Woodstock!” We got married in Woodstock in September of 2012 and decided to take a trip back to explore without the pressure of planning or having a wedding. We normally stayed at the Woodstock Inn, but no longer. The apartment exc
    …see more

    Price per night from

    $109

    Price per night from

    $109

    (6) Excellent 

      27

      Woodstock Carriage House! Vermont's finest county road with homes and farms.

      Vermont / Woodstock

      Woodstock house

      2 4 min stay varies

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

      Price per night from

      $252

      Price per night from

      $252

      (1) Excellent 

        0

        Dog-friendly house w/ charm & entertainment - 4 miles to nearest ski slopes!

        Vermont / Woodstock

        Woodstock house

        3 8 2 nights min

        • 3 bedrooms
        • sleeps 8
        • 2 nights min
        • Child Friendly
        • Car not necessary
        • Pet Friendly

        Price per night from

        $115

        Price per night from

        $115

          6

          Luxury Apartment Over Brook, Near Village

          Vermont / Woodstock

          Woodstock apartment

          2 6 3 nights min

          • 2 bedrooms
          • sleeps 6
          • 3 nights min
          • Beach / lakeside relaxation

          Price per night from

          $288

          Price per night from

          $288

            6

            Serene, Modern Escape, Overlooking Quiet Brook

            Vermont / Woodstock

            Woodstock apartment

            1 4 3 nights min

            • 1 bedroom
            • sleeps 4
            • 3 nights min
            • Beach / lakeside relaxation
            • Ski
            • Ask about children

            Price per night from

            $258

            Price per night from

            $258

            Great rentals within 20 miles that match your search

            Distance approx 14.6 km from Woodstock

            (69) Excellent 

              31

              Cozy country cabins with all the comforts of home!

              Vermont / South Royalton

              South Royalton log cabin

              2 3 min stay varies

              • 2 bedrooms
              • sleeps 3
              • min stay varies
              • Beach / lakeside relaxation
              • Child Friendly
              • Air conditioning
              “A great cozy get away!” My boyfriend and I stayed at the upper cabin last week and it was just what we needed to relax. The cabin is beautifully decorated to make you feel right at home. The gas fire place in the living room really makes the cabin toa
              …see more

              Price per night from

              $219

              Price per night from

              $219

              Distance approx 13.58 km from Woodstock

                25

                Inviting 3BR + Loft Hanover House w/Gorgeous Views

                New Hampshire / Hanover

                Hanover house

                3 7 30 nights min

                • 3 bedrooms
                • sleeps 7
                • 30 nights min
                • Child Friendly
                • Air conditioning

                Price per night from

                $150

                Responds fast!
                avg. 21 minutes

                Price per night from

                $150

                Distance approx 13.16 km from Woodstock

                (1) Excellent 

                  24

                  'Serenity at Sunrise' Townhome by Bear Mountain!

                  Vermont / Killington

                  Killington house

                  3 6 min stay varies

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

                  Price per night from

                  $288

                  Responds fast!
                  avg. 38 minutes

                  Price per night from

                  $288

                  Distance approx 18.99 km from Woodstock

                    27

                    Ludlow Cabin Near Okemo Ski Lodge

                    Vermont / Ludlow

                    Ludlow house

                    3 6 2 nights min

                    • 3 bedrooms
                    • sleeps 6
                    • 2 nights min
                    • Beach / lakeside relaxation
                    • Ski
                    • Child Friendly

                    Price per night from

                    $288

                    Price per night from

                    $288

                    Distance approx 12.98 km from Woodstock

                      25

                      Upper unit of Chalet, minutes to Killington, Okemo or Woodstock

                      Vermont / Plymouth

                      Plymouth house

                      2 6 2 nights min

                      • 2 bedrooms
                      • sleeps 6
                      • 2 nights min
                      • Nearest beach 1 mi
                      • Child Friendly
                      • Pet Friendly

                      Price per night from

                      $403

                      Price per night from

                      $403

                      Distance approx 17.15 km from Woodstock

                      (2) Excellent 

                        11

                        Ski-in/out Luxury 3 Bedroom & 3 Bathroom Okemo Penthouse Condo at Jackson Gore

                        Vermont / Ludlow

                        Ludlow apartment

                        4 10 2 nights min

                        • 4 bedrooms
                        • sleeps 10
                        • 2 nights min
                        • Swimming pool
                        • Ski
                        • Child Friendly

                        Price per night from

                        $1,490

                        Price per night from

                        $1,490

                        Distance approx 13.8 km from Woodstock

                        (1) Excellent 

                          20

                          Hideaway Chalet Comfort for 24 close to ski slopes walk to restaurants HOT TUB

                          Vermont / Killington

                          Killington house

                          8 24 2 nights min

                          • 8 bedrooms
                          • sleeps 24
                          • 2 nights min
                          • Child Friendly
                          • Private garden

                          Price per night from

                          $1,013

                          Price per night from

                          $1,013

                          Distance approx 13 km from Woodstock

                          (1) Excellent 

                            54

                            The Lodges Bear Mountain Luxury ski-on/ski-off 3 bed 3 Bath LOW RATES-Mar/Apr

                            Vermont / Killington

                            Killington condo

                            3 8 3 nights min

                            • 3 bedrooms
                            • sleeps 8
                            • 3 nights min
                            • Swimming pool
                            • Child Friendly
                            • Pet Friendly

                            Price per night from

                            $340

                            Price per night from

                            $340

                            Distance approx 14.06 km from Woodstock

                            (4) Very Good 

                              20

                              Secluded, Spectacular House with Mount Ascutney Vi

                              Vermont / Perkinsville

                              Perkinsville house

                              5 12 min stay varies

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

                              Price per night from

                              $259

                              Price per night from

                              $259

                              Distance approx 19.54 km from Woodstock

                                16

                                South Face Village

                                Vermont / Ludlow

                                Ludlow condo

                                2 6 2 nights min

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

                                Price per night from

                                $518

                                Price per night from

                                $518

                                Distance approx 4.4 km from Woodstock Show on Map

                                  11

                                  Lovely Condo / Townhouse in the Heart of Quechee

                                  Hartford / Quechee

                                  Quechee townhouse

                                  2 6 2 nights min

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

                                  Price per night from

                                  $181

                                  Price per night from

                                  $181

                                  Distance approx 9.94 km from Woodstock

                                    20

                                    Great Bear Lodge

                                    Vermont / Sharon

                                    Sharon house

                                    5 9 2 nights min

                                    • 5 bedrooms
                                    • sleeps 9
                                    • 2 nights min
                                    • Child Friendly
                                    • Pet Friendly
                                    • Private garden

                                    Price per night from

                                    $344

                                    Price per night from

                                    $344

                                    Distance approx 18.5 km from Woodstock

                                      16

                                      Okemo Slopeside Rental located at the Main Base!

                                      Vermont / Ludlow

                                      Ludlow condo

                                      1 2 2 nights min

                                      • 1 bedroom
                                      • sleeps 2
                                      • 2 nights min
                                      • Ski
                                      • Child Friendly

                                      Price per night from

                                      $431

                                      Price per night from

                                      $431

                                      Distance approx 17.47 km from Woodstock

                                        9

                                        Spotless newer ski home

                                        Vermont / Cavendish

                                        Cavendish house

                                        4 8 2 nights min

                                        • 4 bedrooms
                                        • sleeps 8
                                        • 2 nights min
                                        • Child Friendly
                                        • Private garden

                                        Price per night from

                                        $518

                                        Price per night from

                                        $518

                                        Distance approx 13.89 km from Woodstock

                                          23

                                          Suites at killington Center

                                          Vermont / Killington

                                          Killington condo

                                          2 6 2 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 2 nights min
                                          • Swimming pool
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $345

                                          Price per night from

                                          $345

                                          Distance approx 13.86 km from Woodstock

                                            24

                                            Mt Green 1-A8

                                            Vermont / Killington

                                            Killington apartment

                                            1 5 min stay varies

                                            • 1 bedroom
                                            • sleeps 5
                                            • min stay varies
                                            • Swimming pool
                                            • Child Friendly
                                            • Car not necessary

                                            Price per night from

                                            $170

                                            Price per night from

                                            $170

                                            Distance approx 13.86 km from Woodstock

                                              24

                                              Mt Green 1-B3

                                              Vermont / Killington

                                              Killington apartment

                                              2 6 min stay varies

                                              • 2 bedrooms
                                              • sleeps 6
                                              • min stay varies
                                              • Swimming pool
                                              • Child Friendly
                                              • Car not necessary

                                              Price per night from

                                              $228

                                              Price per night from

                                              $228

                                              Distance approx 18.31 km from Woodstock

                                                14

                                                Clean, Cozy and Centrally located 3 BR Townhouse

                                                Vermont / Ludlow

                                                Ludlow house

                                                3 10 3 nights min

                                                • 3 bedrooms
                                                • sleeps 10
                                                • 3 nights min
                                                • Child Friendly

                                                Price per night from

                                                $144

                                                Responds fast!
                                                avg. 2 hours 55 minutes

                                                Price per night from

                                                $144

                                                Distance approx 13.91 km from Woodstock

                                                  28

                                                  Mountain Green Recently Updated 1 BR Condo Across The Street From Snowshed Lodge

                                                  Vermont / Killington

                                                  Killington condo

                                                  1 4 2 nights min

                                                  • 1 bedroom
                                                  • sleeps 4
                                                  • 2 nights min
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $247

                                                  Responds fast!
                                                  avg. 1 hour 27 minutes

                                                  Price per night from

                                                  $247

                                                  Distance approx 12.78 km from Woodstock

                                                    24

                                                    Plymouth Home w/ Jacuzzi Near Okemo & Killington!

                                                    Vermont / Plymouth

                                                    Plymouth house

                                                    5 12 min stay varies

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

                                                    Price per night from

                                                    $392

                                                    Responds fast!
                                                    avg. 21 minutes

                                                    Price per night from

                                                    $392

                                                    Distance approx 13.91 km from Woodstock

                                                      24

                                                      Mt Green 3-C4

                                                      Vermont / Killington

                                                      Killington apartment

                                                      2 8 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 8
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Car not necessary

                                                      Price per night from

                                                      $219

                                                      Price per night from

                                                      $219

                                                      Distance approx 13.91 km from Woodstock

                                                        24

                                                        Mt Green 3-A6

                                                        Vermont / Killington

                                                        Killington apartment

                                                        2 6 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Car not necessary

                                                        Price per night from

                                                        $217

                                                        Price per night from

                                                        $217

                                                        Distance approx 7.45 km from Woodstock Show on Map

                                                          24

                                                          Bridgewater Country Cottage

                                                          Vermont / Bridgewater

                                                          Bridgewater house

                                                          4 10 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 10
                                                          • min stay varies
                                                          • Car not necessary
                                                          • Pet Friendly

                                                          Price per night from

                                                          $240

                                                          Price per night from

                                                          $240

                                                          Distance approx 18.81 km from Woodstock

                                                            16

                                                            Quiet Hillside 4 Bedroom Carriage House W/3 Baths

                                                            Vermont / Ludlow

                                                            Ludlow guest house

                                                            5 10 2 nights min

                                                            • 5 bedrooms
                                                            • sleeps 10
                                                            • 2 nights min
                                                            • Child Friendly

                                                            Price per night from

                                                            $346

                                                            Price per night from

                                                            $346

                                                            Distance approx 13.5 km from Woodstock

                                                              24

                                                              NEW! Ski-in Condo - 2 Mi to Killington Ski Area!

                                                              Vermont / Killington

                                                              Killington condo

                                                              3 8 min stay varies

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

                                                              Price per night from

                                                              $230

                                                              Responds fast!
                                                              avg. 21 minutes

                                                              Price per night from

                                                              $230

                                                              Distance approx 13.81 km from Woodstock

                                                                24

                                                                Mt Green 2-E9

                                                                Vermont / Killington

                                                                Killington apartment

                                                                1 4 min stay varies

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

                                                                Price per night from

                                                                $170

                                                                Price per night from

                                                                $170

                                                                Distance approx 16.49 km from Woodstock

                                                                  0

                                                                  Family lodge w/ deck & fireplace - just a short drive to Killington & Pico Mtn!

                                                                  Vermont / Killington

                                                                  Killington house

                                                                  3 8 2 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 2 nights min
                                                                  • Child Friendly
                                                                  • Car not necessary

                                                                  Price per night from

                                                                  $172

                                                                  Responds fast!
                                                                  avg. 1 hour 28 minutes

                                                                  Price per night from

                                                                  $172

                                                                  Distance approx 13.91 km from Woodstock

                                                                    24

                                                                    Mt Green 3-D8

                                                                    Vermont / Killington

                                                                    Killington apartment

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Car not necessary

                                                                    Price per night from

                                                                    $209

                                                                    Price per night from

                                                                    $209

                                                                    Distance approx 15.86 km from Woodstock

                                                                      20

                                                                      Cabin in the Big Woods - sleeping porch lake trails playground

                                                                      Vermont / Mount Holly

                                                                      Mount Holly log cabin

                                                                      1 6 2 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 6
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $92

                                                                      Price per night from

                                                                      $92

                                                                      Distance approx 13.05 km from Woodstock

                                                                      (2) Very Good 

                                                                        24

                                                                        Premier Ski-in/Ski-out Location, Sunrise Mountain

                                                                        Vermont / Killington

                                                                        Killington apartment

                                                                        1 4 2 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • 2 nights min
                                                                        • Swimming pool
                                                                        • Ask about children
                                                                        • Ask about pets

                                                                        Price per night from

                                                                        $374

                                                                        Price per night from

                                                                        $374

                                                                        Distance approx 13.86 km from Woodstock

                                                                          24

                                                                          Mt Green 1-C8 ~ RA80777

                                                                          Vermont / Killington

                                                                          Killington apartment

                                                                          1 4 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Child Friendly
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $161

                                                                          Price per night from

                                                                          $161

                                                                          Distance approx 16.3 km from Woodstock

                                                                            18

                                                                            Pico Village Resort H304

                                                                            Vermont / Killington

                                                                            Killington condo

                                                                            2 8 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 8
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Car not necessary

                                                                            Price per night from

                                                                            $247

                                                                            Price per night from

                                                                            $247

                                                                            Distance approx 13.91 km from Woodstock

                                                                            (1)  

                                                                              7

                                                                              Mountain Green WLK 2 LIFT/Access RD. Kilington VT

                                                                              Vermont / Killington

                                                                              Killington condo

                                                                              2 6 2 nights min

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

                                                                              Price per night from

                                                                              $202

                                                                              Responds fast!
                                                                              avg. 23 minutes

                                                                              Price per night from

                                                                              $202

                                                                              About Woodstock

                                                                              With numerous options for outdoor recreational activities, interesting historical sites, and friendly locals, the Vermont town of Woodstock has it all! Central Street is the primary commercial shopping district in Woodstock, but you can also visit The Green for some of the best restaurants that the state has to offer.

                                                                              Here are a few additional suggestions of things to do in Woodstock:

                                                                              • Billings Farm and Museum: Visit this 270 acre farm, dairy barn, and museum with historic artifacts.
                                                                              • Ottaquechee River: This river that runs through Woodstock offers plenty of opportunities for fishing and canoeing excursions.
                                                                              • Dana House: This small museum hosts several pieces of artwork and historic artifacts from the local area in the 19th century.
                                                                              • Mount Tom: Climb to the top of Woodstock's main mountain for stunning views of the town and surrounding areas.

                                                                              There are many events and festivals held throughout the year in Woodstock that bring the whole community together. Watch the parade through town featuring horses and costumed riders during Wassail weekend in February, sample artwork from the top painters and sculptors in the region during the Woodstock Art Festival in September, or try the local cuisine from the best chefs and brewers in the state during the Taste of Woodstock event in September.

                                                                              To get the most out of your time in Woodstock, stay in a vacation rental. Rent a villa or condo close to the historic sites throughout town, or book a cozy cabin with amazing mountain views right outside your door.

                                                                              If you wish to explore the rest of the region, Woodstock is only a short drive from some of the other popular towns and cities in Vermont. The hiking options found in Rutland and the colonial village of Barre can both be reached within an hour by car.