Have Fun by Choosing Woodstock, VT Rentals

Loved as a top vacation spot, Woodstock, Vermont has all the charm and character a vacation-bound family needs, no matter what season it is.

Woodstock, VT Rentals Welcome You Home


This quaint New England village offers plenty to enjoy! You should plan on staying in one of the many elegant Woodstock, VT rentals while you are here. Woodstock vacation rentals have all the comforts of home combined with unique architecture and a comfortable atmosphere. Perhaps one of the Woodstock cabins nestled in the arms of the forest would be to your liking. Wake refreshed after a good night’s sleep and you will easily see why families love to vacation in these cabins.

Enjoy the Hospitality of Woodstock Vacation Rentals


Cross the covered bridge into the heart of our town and you cross into another era of American life. Woodstock, VT rentals are conveniently located near a fine selection of galleries, art studios, unique shops, and antique stores, but you still feel immersed in an atmosphere of antiquity. Woodstock vacation rentals accommodate almost any size family with comfortable living spaces.

Woodstock cabins give you easy access to the many activities our town has to offer, such as fishing, golf, hiking, biking or skiing. Active families find plenty of entertainment possibilities!

Woodstock Cabins in the Heart of Mother Nature


The fall colors in the area are absolutely breathtaking. You may want to spend some of your summer time in one of the Woodstock, VT rentals, enjoying the water features scattered throughout. Wintertime brings crisp air and a fairly mild climate with plenty of snow.

Spring visitors are perhaps luckiest. Woodstock vacation rentals are often surrounded by nature; you can wake up in the early spring as the snow finally melts away. Leave your troubles behind and stay in one of the comfortable Woodstock cabins!

Other options for Eastern Vermont vacation rentals include Barnard accommodations, vacation homes in Brownsville VT, Fairlee cabin rentals, or lodging in Quechee.


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Woodstock: Houses, Farmhouses & More(42)

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Beautiful Residence Full Of Character And Charm
    5 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 14
$250 - $300
per night

Beautiful Residence Full Of Character And Charm

3 night Minimum Stay
  • 5 BR,
  • 3 BA,
  • Sleeps 14
  1. Eastern Vermont >
  2. Woodstock House
#200949
    (19)
    Breathtaking views, luxury and solitude just minutes from the center of town.
      6 Bedrooms,
    • 4 Bathrooms
      • , Sleeps 14
    $2,125 - $5,500
    per week

    Breathtaking views, luxury and solitude just minutes from the center of town.

    7 night Minimum Stay
    • 6 BR,
    • 4 BA,
    • Sleeps 14
    1. Eastern Vermont >
    2. Woodstock Estate
    #921704
      (5)
      Brand New Home in Downtown Woodstock
        3 Bedrooms,
      • 2 Bathrooms, 
      • 1 Half Bath
        • , Sleeps 8
      $500 - $600
      per night

      Brand New Home in Downtown Woodstock

      2 night Minimum Stay
      • 3 BR,
      • 2 BA,
      • 1 HF BA,
      • Sleeps 8
      1. Eastern Vermont >
      2. Woodstock House
      #440850vb
        Spacious Hilltop Home with Expansive Views and 5 min Walk to Town
          4 Bedrooms,
        • 4 Bathrooms, 
        • 1 Half Bath
          • , Sleeps 9
        $4,000
        per week

        Spacious Hilltop Home with Expansive Views and 5 min Walk to Town

        7 night Minimum Stay
        • 4 BR,
        • 4 BA,
        • 1 HF BA,
        • Sleeps 9
        1. Eastern Vermont >
        2. Woodstock House
        #3479061
          2 Reviews
          The Best Location on Silver Lake..
            2 Bedrooms,
          • 2 Bathrooms, 
          • 1 Half Bath
            • , Sleeps 8
          $215 - $350
          per night

          The Best Location on Silver Lake..

          3 night Minimum Stay
          • 2 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 8
          1. Eastern Vermont >
          2. Woodstock House
          #3319943
            (9)
            Charming Victorian “Doll House” in Village
              2 Bedrooms,
            • 2 Bathrooms
              • , Sleeps 6
            $200 - $225
            per night

            Charming Victorian “Doll House” in Village

            2 night Minimum Stay
            • 2 BR,
            • 2 BA,
            • Sleeps 6
            1. Eastern Vermont >
            2. Woodstock House
            #186339
              (33)
              Woodstock village log home apartment, SUMMERTIME DESTINATION
                1 Bedrooms,
              • 1 Bathroom
                • , Sleeps 4
              $110 - $175
              per night

              Woodstock village log home apartment, SUMMERTIME DESTINATION

              2 - 3 night Minimum Stay
              • 1 BR,
              • 1 BA,
              • Sleeps 4
              1. Eastern Vermont >
              2. Woodstock Apartment
              #354330
                (39)
                Woodstock Four Season Family Estate Has It All!
                  6 Bedrooms,
                • 4 Bathrooms
                  • , Sleeps 12
                $750
                per night

                Woodstock Four Season Family Estate Has It All!

                2 night Minimum Stay
                • 6 BR,
                • 4 BA,
                • Sleeps 12
                1. Eastern Vermont >
                2. Woodstock Farmhouse
                #3482379
                  Family Reunion Hilltop Getaway
                    7 Bedrooms,
                  • 4 Bathrooms
                    • , Sleeps 14

                  Family Reunion Hilltop Getaway

                  • 7 BR,
                  • 4 BA,
                  • Sleeps 14
                  1. Eastern Vermont >
                  2. Woodstock House
                  #328302
                    (12)
                    Woodstock VT House in the Country - 3BR/2BA A Beautiful Vermont Vacation Home
                      3 Bedrooms,
                    • 2 Bathrooms
                      • , Sleeps 6
                    $280 - $290
                    per night

                    Woodstock VT House in the Country - 3BR/2BA A Beautiful Vermont Vacation Home

                    3 night Minimum Stay
                    • 3 BR,
                    • 2 BA,
                    • Sleeps 6
                    1. Eastern Vermont >
                    2. Woodstock House
                    #223034
                      (8)
                      Charming, Cozy, Spacious Killington/Woodstk House Near Woodstock Village
                        4 Bedrooms,
                      • 3 Bathrooms
                        • , Sleeps 10
                      $165 - $250
                      per night

                      Charming, Cozy, Spacious Killington/Woodstk House Near Woodstock Village

                      2 night Minimum Stay
                      • 4 BR,
                      • 3 BA,
                      • Sleeps 10
                      1. Eastern Vermont >
                      2. Woodstock Farmhouse
                      #363145
                        (20)
                        Just Outside Village w/ Privacy, Views & Amenities
                          4 Bedrooms,
                        • 2 Bathrooms
                          • , Sleeps 8
                        $2,100 - $3,000
                        per week

                        Just Outside Village w/ Privacy, Views & Amenities

                        7 night Minimum Stay
                        • 4 BR,
                        • 2 BA,
                        • Sleeps 8
                        1. Eastern Vermont >
                        2. Woodstock House
                        #104617
                          5 Reviews
                          Woodstock Village Elegance and Big views
                            3 Bedrooms,
                          • 2 Bathrooms, 
                          • 1 Half Bath
                            • , Sleeps 6
                          $475 - $550
                          per night

                          Woodstock Village Elegance and Big views

                          3 night Minimum Stay
                          • 3 BR,
                          • 2 BA,
                          • 1 HF BA,
                          • Sleeps 6
                          1. Eastern Vermont >
                          2. Woodstock House
                          #339119
                            1 Review
                            250 Private Acres; Views, Gardens, Skiing, Woodstock, Best of VT
                              2 Bedrooms,
                            • 1 Bathroom
                              • , Sleeps 4
                            $225 - $250
                            per night

                            250 Private Acres; Views, Gardens, Skiing, Woodstock, Best of VT

                            3 night Minimum Stay
                            • 2 BR,
                            • 1 BA,
                            • Sleeps 4
                            1. Eastern Vermont >
                            2. Woodstock House
                            #104613
                              2 Reviews
                              Woodstock, Vermont -
                                4 Bedrooms,
                              • 3 Bathrooms
                                • , Sleeps 10
                              $3,200 - $3,800
                              per week

                              Woodstock, Vermont -

                              2 night Minimum Stay
                              • 4 BR,
                              • 3 BA,
                              • Sleeps 10
                              1. Eastern Vermont >
                              2. Woodstock Farmhouse
                              #130026
                                (13)
                                Charming 1782 estate, completely renovated, quiet country lane
                                  4 Bedrooms,
                                • 4 Bathrooms, 
                                • 1 Half Bath
                                  • , Sleeps 10
                                $3,800 - $4,000
                                per week

                                Charming 1782 estate, completely renovated, quiet country lane

                                2 night Minimum Stay
                                • 4 BR,
                                • 4 BA,
                                • 1 HF BA,
                                • Sleeps 10
                                1. Eastern Vermont >
                                2. Woodstock Estate
                                #353533
                                  (6)
                                  Sterling Cottage: Two Miles from Woodstock Village Green.
                                    1 Bedrooms,
                                  • 1 Bathroom
                                    • , Sleeps 4
                                  $125 - $175
                                  per night

                                  Sterling Cottage: Two Miles from Woodstock Village Green.

                                  2 night Minimum Stay
                                  • 1 BR,
                                  • 1 BA,
                                  • Sleeps 4
                                  1. Eastern Vermont >
                                  2. Woodstock Cottage
                                  #318584
                                    (7)
                                    Luxurious Historic Barn
                                      2 Bedrooms,
                                    • 1 Bathroom, 
                                    • 1 Half Bath
                                      • , Sleeps 8
                                    $225 - $275
                                    per night

                                    Luxurious Historic Barn

                                    2 - 4 night Minimum Stay
                                    • 2 BR,
                                    • 1 BA,
                                    • 1 HF BA,
                                    • Sleeps 8
                                    1. Eastern Vermont >
                                    2. Woodstock House
                                    #3003186
                                      (10)
                                      Classic Country Cottage for Romantic Getaway. Safe. Private. Views.
                                        3 Bedrooms,
                                      • 2 Bathrooms
                                        • , Sleeps 7
                                      $350
                                      per night

                                      Classic Country Cottage for Romantic Getaway. Safe. Private. Views.

                                      2 night Minimum Stay
                                      • 3 BR,
                                      • 2 BA,
                                      • Sleeps 7
                                      1. Eastern Vermont >
                                      2. Woodstock Cottage
                                      #119014
                                        (6)
                                        Perfect Design and Location for the Vermont Experience
                                          3 Bedrooms,
                                        • 2 Bathrooms
                                          • , Sleeps 10
                                        $1,100
                                        per week

                                        Perfect Design and Location for the Vermont Experience

                                        3 night Minimum Stay
                                        • 3 BR,
                                        • 2 BA,
                                        • Sleeps 10
                                        1. Eastern Vermont >
                                        2. Woodstock House
                                        #125564
                                          (10)
                                          Gilbert Hill Getaway
                                            3 Bedrooms,
                                          • 1 Bathroom
                                            • , Sleeps 6
                                          $200 - $250
                                          per night

                                          Gilbert Hill Getaway

                                          2 night Minimum Stay
                                          • 3 BR,
                                          • 1 BA,
                                          • Sleeps 6
                                          1. Eastern Vermont >
                                          2. Woodstock Barn
                                          #964391
                                            (3)
                                            Lovely Antique Home In The Heart Of Woodstock Village
                                              4 Bedrooms,
                                            • 2 Bathrooms, 
                                            • 2 Half Baths
                                              • , Sleeps 8
                                            $2,000 - $2,400
                                            per week

                                            Lovely Antique Home In The Heart Of Woodstock Village

                                            3 - 7 night Minimum Stay
                                            • 4 BR,
                                            • 2 BA,
                                            • 2 HF BA,
                                            • Sleeps 8
                                            1. Eastern Vermont >
                                            2. Woodstock House
                                            #284798
                                              Woodstock Farmhouse
                                                2 Bedrooms,
                                              • 1 Bathroom, 
                                              • 1 Half Bath
                                                • , Sleeps 6
                                              $135 - $150
                                              per night

                                              Woodstock Farmhouse

                                              3 night Minimum Stay
                                              • 2 BR,
                                              • 1 BA,
                                              • 1 HF BA,
                                              • Sleeps 6
                                              1. Eastern Vermont >
                                              2. Woodstock House
                                              #175573
                                                Tranquil Setting Nestled Into the Village of South Woodstock
                                                  3 Bedrooms,
                                                • 2 Bathrooms, 
                                                • 1 Half Bath
                                                  • , Sleeps 10

                                                Tranquil Setting Nestled Into the Village of South Woodstock

                                                • 3 BR,
                                                • 2 BA,
                                                • 1 HF BA,
                                                • Sleeps 10
                                                1. Eastern Vermont >
                                                2. Woodstock House
                                                #393349
                                                  13 Reviews
                                                  Scenic South Woodstock, Vermont home
                                                    4 Bedrooms,
                                                  • 2 Bathrooms, 
                                                  • 1 Half Bath
                                                    • , Sleeps 6
                                                  $1,400
                                                  per week

                                                  Scenic South Woodstock, Vermont home

                                                  2 night Minimum Stay
                                                  • 4 BR,
                                                  • 2 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 6
                                                  1. Eastern Vermont >
                                                  2. Woodstock House
                                                  #189992
                                                    (8)
                                                    Leave No Trace - Cozy Furnished Log Cabin in Woods
                                                      2 Bedrooms,
                                                    • 2 Bathrooms
                                                      • , Sleeps 6
                                                    $140 - $180
                                                    per night

                                                    Leave No Trace - Cozy Furnished Log Cabin in Woods

                                                    2 night Minimum Stay
                                                    • 2 BR,
                                                    • 2 BA,
                                                    • Sleeps 6
                                                    1. Eastern Vermont >
                                                    2. Woodstock Cabin
                                                    #104614
                                                      Charming Post and Beam house
                                                        3 Bedrooms,
                                                      • 2 Bathrooms, 
                                                      • 1 Half Bath
                                                        • , Sleeps 10
                                                      $200 - $225
                                                      per night

                                                      Charming Post and Beam house

                                                      2 night Minimum Stay
                                                      • 3 BR,
                                                      • 2 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 10
                                                      1. Eastern Vermont >
                                                      2. Woodstock House
                                                      #258340
                                                        **New Rental Listing- Interior Designers own Woodstock retreat
                                                          4 Bedrooms,
                                                        • 3 Bathrooms
                                                          • , Sleeps 10

                                                        **New Rental Listing- Interior Designers own Woodstock retreat

                                                        • 4 BR,
                                                        • 3 BA,
                                                        • Sleeps 10
                                                        1. Eastern Vermont >
                                                        2. Woodstock Farmhouse
                                                        #3320446
                                                          4 Reviews
                                                          Woodstock village condominium
                                                            2 Bedrooms,
                                                          • 2 Bathrooms
                                                            • , Sleeps 4
                                                          $250
                                                          per night

                                                          Woodstock village condominium

                                                          2 night Minimum Stay
                                                          • 2 BR,
                                                          • 2 BA,
                                                          • Sleeps 4
                                                          1. Eastern Vermont >
                                                          2. Woodstock Condo
                                                          #127203
                                                            (5)
                                                            Classic Brick Cape Available for Woodstock Winter Rental
                                                              4 Bedrooms,
                                                            • 2 Bathrooms, 
                                                            • 1 Half Bath
                                                              • , Sleeps 8
                                                            $5,000
                                                            per month

                                                            Classic Brick Cape Available for Woodstock Winter Rental

                                                            28 night Minimum Stay
                                                            • 4 BR,
                                                            • 2 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 8
                                                            1. Eastern Vermont >
                                                            2. Woodstock House
                                                            #3471522
                                                              • 1 - 30 of 42
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