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111 Houses

    11

    Country Farmhouse with Views

    Green Mountains / Shaftsbury

    Shaftsbury house

    4 6 3 nights min

    • 4 bedrooms
    • sleeps 6
    • 3 nights min
    • Child Friendly
    • Air conditioning
    • Private garden

    Price per night from

    $399

    Price per night from

    $399

    Great rentals within 20 miles that match your search

    Distance approx 16.89 km from Shaftsbury

    (1) Excellent 

      16

      Spacious Modern Ski Home near The Hermitage / Mt. Snow

      Vermont / Dover

      Dover house

      4 12 7 nights min

      • 4 bedrooms
      • sleeps 12
      • 7 nights min
      • Child Friendly
      • Pet Friendly
      • Private garden

      Price per night from

      $423

      Price per night from

      $423

      Distance approx 16.81 km from Shaftsbury

      (1) Very Good 

        13

        Mount Snow Area Home with 5 Bedrooms

        Vermont / Wilmington

        Wilmington house

        5 12 2 nights min

        • 5 bedrooms
        • sleeps 12
        • 2 nights min
        • Child Friendly
        • Car not necessary
        • Pet Friendly

        Price per night from

        $343

        Price per night from

        $343

        Distance approx 17.77 km from Shaftsbury

          20

          "Not Your Typical Rental" Luxe Burke Mtn 3br Condo

          Northeast Kingdom / East Burke

          East Burke condo

          3 8 2 nights min

          • 3 bedrooms
          • sleeps 8
          • 2 nights min
          • Child Friendly
          • Ask about pets

          Price per night from

          $372

          Price per night from

          $372

          Distance approx 16.6 km from Shaftsbury

            17

            Beautiful Cabin in a Peaceful 4 Season Resort with Club House Amenities

            Vermont / Wilmington

            Wilmington chalet

            6 15 2 nights min

            • 6 bedrooms
            • sleeps 15
            • 2 nights min
            • Swimming pool
            • Child Friendly
            • Pet Friendly

            Price per night from

            $366

            Price per night from

            $366

            Distance approx 17.55 km from Shaftsbury

              10

              Mount Snow 6BR+ Indoor Hot Tub, Sauna, Pool Table, FANTASY Ski Home

              Vermont / Dover

              Dover house

              6 18 3 nights min

              • 6 bedrooms
              • sleeps 18
              • 3 nights min
              • Child Friendly
              • Private garden

              Price per night from

              $915

              Price per night from

              $915

              Distance approx 17.63 km from Shaftsbury

                37

                3 BR apartment, walking distance to Mass MoCa

                Berkshires / North Adams

                North Adams apartment

                3 15 min stay varies

                • 3 bedrooms
                • sleeps 15
                • min stay varies
                • Ski
                • Child Friendly
                • Car not necessary

                Price per night from

                $212

                Price per night from

                $212

                Distance approx 16.02 km from Shaftsbury

                  17

                  House On Main Street

                  Berkshires / Williamstown

                  Williamstown house

                  4 16 2 nights min

                  • 4 bedrooms
                  • sleeps 16
                  • 2 nights min
                  • Child Friendly
                  • Car not necessary
                  • Air conditioning

                  Price per night from

                  $573

                  Responds fast!
                  avg. 1 hour 19 minutes

                  Price per night from

                  $573

                  Distance approx 10.86 km from Shaftsbury

                    16

                    Quiet Study in the Rancher's House

                    New York / Cambridge

                    Cambridge guest house

                    1 2 1 night min

                    • 1 bedroom
                    • sleeps 2
                    • 1 night min
                    • Child Friendly
                    • Air conditioning
                    • Private garden

                    Price per night from

                    $58

                    Price per night from

                    $58

                    Distance approx 17.34 km from Shaftsbury

                    (2) Excellent 

                      18

                      Boorn Brook Farm - Historic Renovated 1820's Barn - Skiing, Shopping, Relaxing

                      Green Mountains / Manchester

                      Manchester barn

                      2 5 2 nights min

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

                      Price per night from

                      $458

                      Price per night from

                      $458

                      Distance approx 8.19 km from Shaftsbury

                      (1) Excellent 

                        13

                        Cozy Lakefront Cottage

                        Vermont / Somerset

                        Somerset cottage

                        3 6 3 nights min

                        • 3 bedrooms
                        • sleeps 6
                        • 3 nights min
                        • Child Friendly
                        • Ask about pets

                        Price per night from

                        $172

                        Price per night from

                        $172

                        Distance approx 17.62 km from Shaftsbury

                          14

                          ROOM walking distance to Mass MoCa

                          Berkshires / North Adams

                          North Adams apartment

                          1 8 min stay varies

                          • 1 bedroom
                          • sleeps 8
                          • min stay varies
                          • Child Friendly
                          • Air conditioning
                          • Pet Friendly

                          Price per night from

                          $115

                          Price per night from

                          $115

                          Distance approx 18.37 km from Shaftsbury

                          (4) Excellent 

                            20

                            Cozy Chalet In The Pines, Only 5 Mi From Mt Snow. UNDER CONSTRUCTION TIL DEC.

                            Vermont / West Wardsboro

                            West Wardsboro chalet

                            2 6 2 nights min

                            • 2 bedrooms
                            • sleeps 6
                            • 2 nights min
                            • Child Friendly
                            • Car not necessary
                            • Private garden
                            “Great cabin, charming, simple and great location!!” We rented from Pat and Marco for a stay around Christmas '14 and was very happy with the cabin. It's just what we wanted - simple, charming and no frills. All that and Pat was very helpful to us when

                            Price per night from

                            $201

                            Responds fast!
                            avg. 3 hours 32 minutes

                            Price per night from

                            $201

                            Distance approx 19.63 km from Shaftsbury

                            (3) Excellent 

                              12

                              2 Bedroom/2 Bath Condo

                              Vermont / Stratton Mountain

                              Stratton Mountain apartment

                              2 5 2 nights min

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

                              Price per night from

                              $344

                              Responds fast!
                              avg. 3 hours 13 minutes

                              Price per night from

                              $344

                              Distance approx 17.37 km from Shaftsbury

                              (1) Excellent 

                                20

                                Five Bedroom Secluded Ski House Located Two Miles From Downtown Manchester

                                Green Mountains / Manchester

                                Manchester house

                                3 10 2 nights min

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

                                Price per night from

                                $315

                                Price per night from

                                $315

                                Distance approx 10.87 km from Shaftsbury

                                  14

                                  The King Rancher's Room

                                  New York / Cambridge

                                  Cambridge guest house

                                  1 2 1 night min

                                  • 1 bedroom
                                  • sleeps 2
                                  • 1 night min
                                  • Child Friendly
                                  • Air conditioning
                                  • Private garden

                                  Price per night from

                                  $58

                                  Price per night from

                                  $58

                                  Distance approx 18.75 km from Shaftsbury

                                  (14) Excellent 

                                    11

                                    The Barn at Four Tooth Farm

                                    Green Mountains / Manchester

                                    Manchester house

                                    1 2 2 nights min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 2 nights min
                                    • Air conditioning
                                    • Private garden
                                    “Felt like home” First class in every way. Beautiful view from the "wall of windows". We found ourselves drinking coffee by the fireplace admiring the view late into the morning rather than getting up and at it.Top notch kitchen if your are inclined t

                                    Price per night from

                                    $343

                                    Responds fast!
                                    avg. 1 hour 48 minutes

                                    Price per night from

                                    $343

                                    Distance approx 17 km from Shaftsbury

                                      24

                                      NEW! Cozy West Dover Home - 3 Miles to Mount Snow!

                                      Vermont / Dover

                                      Dover house

                                      3 8 min stay varies

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

                                      Price per night from

                                      $327

                                      Responds fast!
                                      avg. 7 minutes

                                      Price per night from

                                      $327

                                      Distance approx 17.62 km from Shaftsbury

                                      (2) Excellent 

                                        41

                                        Apartment walking distance to Mass MoCa!!

                                        Berkshires / North Adams

                                        North Adams apartment

                                        2 10 min stay varies

                                        • 2 bedrooms
                                        • sleeps 10
                                        • min stay varies
                                        • Ski
                                        • Child Friendly
                                        • Car not necessary

                                        Price per night from

                                        $201

                                        Price per night from

                                        $201

                                        Distance approx 12.3 km from Shaftsbury

                                          24

                                          Sunderland Vistas, STUNNING VIEWS, Sunset decks

                                          Green Mountains / Manchester

                                          Manchester house

                                          5 10 2 nights min

                                          • 5 bedrooms
                                          • sleeps 10
                                          • 2 nights min
                                          • Child Friendly
                                          • Pet Friendly
                                          • Private garden

                                          Price per night from

                                          $453

                                          Price per night from

                                          $453

                                          Distance approx 8 km from Shaftsbury

                                          (6) Very Good 

                                            6

                                            Mountaintop Cabin w/Waterfront & Amazing View

                                            Green Mountains / Bennington

                                            Bennington chalet

                                            2 6 2 nights min

                                            • 2 bedrooms
                                            • sleeps 6
                                            • 2 nights min
                                            • Beach / lakeside relaxation
                                            • Child Friendly
                                            • Car not necessary

                                            Price per night from

                                            $201

                                            Price per night from

                                            $201

                                            Distance approx 18.59 km from Shaftsbury

                                              28

                                              The Little Farmhouse at Adams Farm

                                              Vermont / Wilmington

                                              Wilmington house

                                              3 6 2 nights min

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

                                              Price per night from

                                              $258

                                              Price per night from

                                              $258

                                              Distance approx 19.02 km from Shaftsbury

                                              (1) Excellent 

                                                24

                                                Repurposed Manchester Barn Close to Town & Skiing!

                                                Green Mountains / Manchester

                                                Manchester cottage

                                                2 5 2 nights min

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

                                                Price per night from

                                                $287

                                                Responds fast!
                                                avg. 7 minutes

                                                Price per night from

                                                $287

                                                Distance approx 18.74 km from Shaftsbury

                                                  26

                                                  NEW! Vermont Getaway w/ Deck - 6 Miles to Mt Snow!

                                                  Vermont / Wilmington

                                                  Wilmington house

                                                  5 12 min stay varies

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

                                                  Price per night from

                                                  $338

                                                  Responds fast!
                                                  avg. 7 minutes

                                                  Price per night from

                                                  $338

                                                  Distance approx 17.33 km from Shaftsbury

                                                    26

                                                    West Dover Home w/Hot Tub- Short Drive to Mt. Snow

                                                    Vermont / Dover

                                                    Dover house

                                                    4 8 min stay varies

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

                                                    Price per night from

                                                    $224

                                                    Responds fast!
                                                    avg. 7 minutes

                                                    Price per night from

                                                    $224

                                                    Distance approx 12.74 km from Shaftsbury

                                                      6

                                                      Beautiful Vacation Home on a Private Lake

                                                      New York / Petersburg

                                                      Petersburg house

                                                      3 7 7 nights min

                                                      • 3 bedrooms
                                                      • sleeps 7
                                                      • 7 nights min
                                                      • Beach / lakeside relaxation
                                                      • Child Friendly

                                                      Price per night from

                                                      $245

                                                      Price per night from

                                                      $245

                                                      Distance approx 16.54 km from Shaftsbury

                                                        24

                                                        NEW! Green Mtn/Finger Lakes Nat'l Forests Townhome

                                                        Vermont / Wilmington

                                                        Wilmington house

                                                        4 12 7 nights min

                                                        • 4 bedrooms
                                                        • sleeps 12
                                                        • 7 nights min
                                                        • Ski
                                                        • Child Friendly
                                                        • Pet Friendly

                                                        Price per night from

                                                        $247

                                                        Responds fast!
                                                        avg. 7 minutes

                                                        Price per night from

                                                        $247

                                                        Distance approx 16.8 km from Shaftsbury

                                                          27

                                                          Pet-Friendly Manchester Home w/ Green Mtn Views!

                                                          Green Mountains / Manchester

                                                          Manchester house

                                                          4 12 min stay varies

                                                          • 4 bedrooms
                                                          • sleeps 12
                                                          • min stay varies
                                                          • Ski
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $344

                                                          Responds fast!
                                                          avg. 7 minutes

                                                          Price per night from

                                                          $344

                                                          Distance approx 16.5 km from Shaftsbury

                                                            24

                                                            Wilmington Home w/Pool Access- 20 Mins to Mt. Snow

                                                            Vermont / Wilmington

                                                            Wilmington house

                                                            3 10 min stay varies

                                                            • 3 bedrooms
                                                            • sleeps 10
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Ski
                                                            • Child Friendly

                                                            Price per night from

                                                            $189

                                                            Responds fast!
                                                            avg. 7 minutes

                                                            Price per night from

                                                            $189

                                                            Distance approx 16.72 km from Shaftsbury

                                                              19

                                                              Beautiful Ski/Golf Chalet on Hermitage Club golf course

                                                              Vermont / Wilmington

                                                              Wilmington house

                                                              4 11 2 nights min

                                                              • 4 bedrooms
                                                              • sleeps 11
                                                              • 2 nights min
                                                              • Child Friendly
                                                              • Pet Friendly
                                                              • Private garden

                                                              Price per night from

                                                              $287

                                                              Price per night from

                                                              $287

                                                              Distance approx 17.54 km from Shaftsbury

                                                              (6) Excellent 

                                                                18

                                                                Family Lodge btwn Stratton & Mt. Snow

                                                                Vermont / Stratton Mountain

                                                                Stratton Mountain house

                                                                5 11 2 nights min

                                                                • 5 bedrooms
                                                                • sleeps 11
                                                                • 2 nights min
                                                                • Child Friendly
                                                                • Private garden

                                                                Price per night from

                                                                $338

                                                                Responds fast!
                                                                avg. 2 hours 52 minutes

                                                                Price per night from

                                                                $338

                                                                Distance approx 15.98 km from Shaftsbury

                                                                  23

                                                                  One of a kind farm stay

                                                                  New York / Greenwich

                                                                  Greenwich farmhouse

                                                                  5 12 2 nights min

                                                                  • 5 bedrooms
                                                                  • sleeps 12
                                                                  • 2 nights min
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $401

                                                                  Price per night from

                                                                  $401

                                                                  Distance approx 19.28 km from Shaftsbury

                                                                    32

                                                                    Manchester Center Home -Patio & Mtn Views

                                                                    Green Mountains / Manchester

                                                                    Manchester house

                                                                    7 22 min stay varies

                                                                    • 7 bedrooms
                                                                    • sleeps 22
                                                                    • min stay varies
                                                                    • Ski
                                                                    • Child Friendly
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $573

                                                                    Responds fast!
                                                                    avg. 7 minutes

                                                                    Price per night from

                                                                    $573

                                                                    Distance approx 17.62 km from Shaftsbury

                                                                      6

                                                                      Partridge Run Ski House - HOT TUB

                                                                      Vermont / Dover

                                                                      Dover house

                                                                      7 29 2 nights min

                                                                      • 7 bedrooms
                                                                      • sleeps 29
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Ask about pets

                                                                      Price per night from

                                                                      $1,718

                                                                      Price per night from

                                                                      $1,718

                                                                      Distance approx 6.71 km from Shaftsbury Show on Map

                                                                        24

                                                                        Private Cambridge Cabin w/Backyard, Fire Pit&Views

                                                                        New York / Cambridge

                                                                        Cambridge house

                                                                        3 10 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 10
                                                                        • min stay varies
                                                                        • Child Friendly
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $287

                                                                        Responds fast!
                                                                        avg. 7 minutes

                                                                        Price per night from

                                                                        $287

                                                                        Distance approx 19.07 km from Shaftsbury

                                                                        (8) Excellent 

                                                                          7

                                                                          Berkshire Getaway

                                                                          Berkshires / North Adams

                                                                          North Adams cottage

                                                                          2 4 1 night min

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • 1 night min
                                                                          • Child Friendly
                                                                          • Pet Friendly
                                                                          “peace and quiet!” This cottage is in a private, peaceful setting. We very much enjoyed our stay. We spent time at the Mass. Museum of Contemporary art in nearby North adams. We visited the summit of Mount Greylock, which was beautiful. We found our ho

                                                                          Price per night from

                                                                          $172

                                                                          Price per night from

                                                                          $172

                                                                          Distance approx 16.36 km from Shaftsbury

                                                                          (6) Excellent 

                                                                            16

                                                                            Condo at Mt. Snow in So VT May 27-30 @ $145/night

                                                                            Vermont / Dover

                                                                            Dover apartment

                                                                            2 8 2 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 8
                                                                            • 2 nights min
                                                                            • Child Friendly
                                                                            “A CONDO TO KEEP COMING BACK TO!” We've rented this condo with friends many times in the past several years, and it's one of our favorites. Steve is very pleasant to deal with, the condo is clean, sleeps many people comfortably, and overlooks the mini

                                                                            Price per night from

                                                                            $401

                                                                            Responds fast!
                                                                            avg. 3 hours 45 minutes

                                                                            Price per night from

                                                                            $401

                                                                            Distance approx 10.89 km from Shaftsbury

                                                                              8

                                                                              The Garden View Room

                                                                              New York / Cambridge

                                                                              Cambridge guest house

                                                                              1 2 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 1 night min
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              Price per night from

                                                                              $58

                                                                              Price per night from

                                                                              $58