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84 Houses

    20

    Karin's Place

    Green Mountains / Bennington

    Bennington house

    7 30 2 nights min

    • 7 bedrooms
    • sleeps 30
    • 2 nights min
    • Swimming pool
    • Child Friendly
    • Air conditioning

    Price per night from

    $1,546

    Price per night from

    $1,546

      20

      Romantic Waterfront Vermont Cottage

      Bennington / North Bennington

      North Bennington house

      1 4 3 nights min

      • 1 bedroom
      • sleeps 4
      • 3 nights min
      • Child Friendly
      • Pet Friendly

      Price per night from

      $188

      Price per night from

      $188

      (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

        Great rentals within 20 miles that match your search

        Distance approx 14.16 km from Bennington

        (1) Excellent 

          21

          Lake House in Berkshires

          Berkshires / North Adams

          North Adams cottage

          1 2 2 nights min

          • 1 bedroom
          • sleeps 2
          • 2 nights min

          Price per night from

          $121

          Price per night from

          $121

          Distance approx 17.52 km from Bennington

            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

            $916

            Price per night from

            $916

            Distance approx 12.97 km from Bennington

            (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 16.5 km from Bennington

                10

                #84: 18 Spring Court 084-01

                Vermont / Wilmington

                Wilmington villa

                3 6 min stay varies

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

                Price per night from

                $275

                Price per night from

                $275

                Distance approx 16.42 km from Bennington

                  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 15.17 km from Bennington

                    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

                    $367

                    Price per night from

                    $367

                    Distance approx 14.78 km from Bennington

                    (1) Excellent 

                      31

                      Sunsets, mountain and meadow views, Hildene Farm, 4 min. to the Equinox Resort

                      Green Mountains / Manchester

                      Manchester house

                      4 8 min stay varies

                      • 4 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Beach / lakeside relaxation
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $390

                      Price per night from

                      $390

                      Distance approx 12.99 km from Bennington

                        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 10.89 km from Bennington

                          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 15.11 km from Bennington

                            10

                            #A59: 88 Howes Loop A059-02

                            Vermont / Wilmington

                            Wilmington villa

                            3 8 min stay varies

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

                            Price per night from

                            $241

                            Price per night from

                            $241

                            Distance approx 18.53 km from Bennington

                              24

                              Cabin w/Deck - Mins to Mt. Snow & Lake Raponda!

                              Vermont / Wilmington

                              Wilmington log cabin

                              2 6 min stay varies

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

                              Price per night from

                              $155

                              Responds fast!
                              avg. 37 minutes

                              Price per night from

                              $155

                              Distance approx 16.5 km from Bennington

                                7

                                #C211: 114 East Brook Crossing C211-03

                                Vermont / Wilmington

                                Wilmington villa

                                3 6 2 nights min

                                • 3 bedrooms
                                • sleeps 6
                                • 2 nights min
                                • Ask about children
                                • Pet Friendly

                                Price per night from

                                $413

                                Price per night from

                                $413

                                Distance approx 16.5 km from Bennington

                                  10

                                  #389: 8 Bear Lair Lane 389-02

                                  Vermont / Wilmington

                                  Wilmington villa

                                  3 7 min stay varies

                                  • 3 bedrooms
                                  • sleeps 7
                                  • min stay varies
                                  • Ask about children
                                  • Pet Friendly

                                  Price per night from

                                  $241

                                  Price per night from

                                  $241

                                  Distance approx 15.04 km from Bennington

                                    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. 47 minutes

                                    Price per night from

                                    $189

                                    Distance approx 16.21 km from Bennington

                                    (5) Excellent 

                                      16

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

                                      Vermont / Dover

                                      Dover apartment

                                      2 8 min stay varies

                                      • 2 bedrooms
                                      • sleeps 8
                                      • min stay varies
                                      • 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
                                      …see more

                                      Price per night from

                                      $382

                                      Price per night from

                                      $382

                                      Distance approx 19.64 km from Bennington

                                      (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
                                        …see more

                                        Price per night from

                                        $201

                                        Responds fast!
                                        avg. 3 hours 32 minutes

                                        Price per night from

                                        $201

                                        Distance approx 16.5 km from Bennington

                                        (1) Excellent 

                                          10

                                          #488: 195 Upper Dam Road 488-01

                                          Vermont / Wilmington

                                          Wilmington villa

                                          5 12 2 nights min

                                          • 5 bedrooms
                                          • sleeps 12
                                          • 2 nights min
                                          • Ask about children
                                          • Pet Friendly

                                          Price per night from

                                          $756

                                          Price per night from

                                          $756

                                          Distance approx 16.36 km from Bennington

                                          (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

                                            $425

                                            Price per night from

                                            $425

                                            Distance approx 15.92 km from Bennington

                                            (1) Very Good 

                                              13

                                              Beautiful Mountainside 2 Bedroom 2 Bath Condominium

                                              Vermont / Dover

                                              Dover condo

                                              2 8 min stay varies

                                              • 2 bedrooms
                                              • sleeps 8
                                              • min stay varies
                                              • Nearest beach 11 mi
                                              • Child Friendly
                                              • Pet Friendly

                                              Price per night from

                                              $187

                                              Price per night from

                                              $187

                                              Distance approx 15.05 km from Bennington

                                                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

                                                Distance approx 15.53 km from Bennington

                                                  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. 47 minutes

                                                  Price per night from

                                                  $247

                                                  Distance approx 18.15 km from Bennington

                                                    21

                                                    New Lakefront Cedar Log Home

                                                    Vermont / Wilmington

                                                    Wilmington chalet

                                                    3 12 2 nights min

                                                    • 3 bedrooms
                                                    • sleeps 12
                                                    • 2 nights min
                                                    • Beach / lakeside relaxation
                                                    • Child Friendly
                                                    • Car not necessary

                                                    Price per night from

                                                    $516

                                                    Responds fast!
                                                    avg. 1 hour 43 minutes

                                                    Price per night from

                                                    $516

                                                    Distance approx 15.53 km from Bennington

                                                    (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

                                                      $344

                                                      Price per night from

                                                      $344

                                                      Distance approx 6.59 km from Bennington

                                                        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

                                                        $516

                                                        Price per night from

                                                        $516

                                                        Distance approx 17.24 km from Bennington

                                                          24

                                                          Awesome! 6BR, Secluded Hot Tub, sleeps 12, WIFI!!

                                                          Vermont / Dover

                                                          Dover house

                                                          6 12 2 nights min

                                                          • 6 bedrooms
                                                          • sleeps 12
                                                          • 2 nights min
                                                          • Child Friendly

                                                          Price per night from

                                                          $487

                                                          Responds fast!
                                                          avg. 1 hour 34 minutes

                                                          Price per night from

                                                          $487

                                                          Distance approx 19.23 km from Bennington

                                                            21

                                                            Mountain Side

                                                            Vermont / Dover

                                                            Dover house

                                                            3 12 2 nights min

                                                            • 3 bedrooms
                                                            • sleeps 12
                                                            • 2 nights min
                                                            • Child Friendly
                                                            • Private garden

                                                            Price per night from

                                                            $859

                                                            Responds fast!
                                                            avg. 1 hour 47 minutes

                                                            Price per night from

                                                            $859

                                                            Distance approx 19.52 km from Bennington

                                                            (1) Very Good 

                                                              4

                                                              Golden Triangle in the Berkshires

                                                              Berkshires / Hancock

                                                              Hancock house

                                                              2 4 2 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 2 nights min
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $2,863

                                                              Price per night from

                                                              $2,863

                                                              Distance approx 12.2 km from Bennington

                                                              (1) Very Good 

                                                                18

                                                                Green Mountain Retreat

                                                                Green Mountains / Sunderland

                                                                Sunderland house

                                                                3 6 min stay varies

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

                                                                Price per night from

                                                                $160

                                                                Price per night from

                                                                $160

                                                                Distance approx 16.5 km from Bennington

                                                                  9

                                                                  #545: 149 Binney Brook Road 545-03

                                                                  Vermont / Wilmington

                                                                  Wilmington villa

                                                                  4 6 2 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 6
                                                                  • 2 nights min
                                                                  • Ask about children
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $413

                                                                  Price per night from

                                                                  $413

                                                                  Distance approx 17.26 km from Bennington

                                                                    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. 47 minutes

                                                                    Price per night from

                                                                    $224

                                                                    Distance approx 15.61 km from Bennington

                                                                      19

                                                                      Beautiful Ski/Golf Chalet on Hermitage Club golf course

                                                                      Vermont / Wilmington

                                                                      Wilmington house

                                                                      4 11 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 11
                                                                      • min stay varies
                                                                      • Child Friendly
                                                                      • Pet Friendly
                                                                      • Private garden

                                                                      Price per night from

                                                                      $287

                                                                      Price per night from

                                                                      $287

                                                                      Distance approx 11.8 km from Bennington

                                                                        68

                                                                        The Lodge at Fox Hollow

                                                                        New York / Petersburg

                                                                        Petersburg house

                                                                        2 7 2 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 7
                                                                        • 2 nights min
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $298

                                                                        Price per night from

                                                                        $298

                                                                        Distance approx 17.74 km from Bennington

                                                                          24

                                                                          Family Home w/Game Room & Sauna-Mins to Mt. Snow!

                                                                          Vermont / Dover

                                                                          Dover house

                                                                          4 8 min stay varies

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

                                                                          Price per night from

                                                                          $373

                                                                          Responds fast!
                                                                          avg. 18 minutes

                                                                          Price per night from

                                                                          $373

                                                                          Distance approx 16.08 km from Bennington

                                                                            31

                                                                            Spacious Home Adjacent to Mt. Snow w/ Game Room!

                                                                            Vermont / Dover

                                                                            Dover house

                                                                            5 13 min stay varies

                                                                            • 5 bedrooms
                                                                            • sleeps 13
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Ski
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $327

                                                                            Responds fast!
                                                                            avg. 47 minutes

                                                                            Price per night from

                                                                            $327

                                                                            Distance approx 17.72 km from Bennington

                                                                              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