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95 Houses

(20) Excellent 

Certificate of Excellence

    26

    HICKORY RIDGE VERMONT LOG CABIN

    Green Mountains / Rupert

    Rupert house

    4 10 min stay varies

    • 4 bedrooms
    • sleeps 10
    • min stay varies
    • Ask about children
    • Pet Friendly

    Certificate of Excellence

    Price per night from

    $207

    Price per night from

    $207

      24

      Rupert Villa w/Private Pool & Large Deck By Dorset

      Green Mountains / Rupert

      Rupert villa

      5 15 min stay varies

      • 5 bedrooms
      • sleeps 15
      • min stay varies
      • Swimming pool
      • Ski
      • Child Friendly

      Price per night from

      $344

      Responds fast!
      avg. 20 minutes

      Price per night from

      $344

      Great rentals within 20 miles that match your search

      Distance approx 12.02 km from Rupert

        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 19.68 km from Rupert

          16

          Newly Remodeled Townhome

          Vermont / Jamaica

          Jamaica townhouse

          3 12 3 nights min

          • 3 bedrooms
          • sleeps 12
          • 3 nights min
          • Swimming pool
          • Child Friendly
          • Pet Friendly

          Price per night from

          $573

          Price per night from

          $573

          Distance approx 14.48 km from Rupert

            20

            Bromley Farm Ski House

            Green Mountains / Peru

            Peru house

            6 14 3 nights min

            • 6 bedrooms
            • sleeps 14
            • 3 nights min
            • Child Friendly
            • Air conditioning
            • Private garden

            Price per night from

            $630

            Price per night from

            $630

            Distance approx 4.78 km from Rupert

            (1) Excellent 

              19

              The Perfect Vermont Experience for All Seasons

              Green Mountains / Dorset

              Dorset house

              4 8 4 nights min

              • 4 bedrooms
              • sleeps 8
              • 4 nights min
              • Child Friendly
              • Air conditioning
              • Ask about pets

              Price per night from

              $287

              Price per night from

              $287

              Distance approx 4.76 km from Rupert

                8

                Dorset in-village summer rental

                Green Mountains / Dorset

                Dorset house

                5 10 14 nights min

                • 5 bedrooms
                • sleeps 10
                • 14 nights min
                • Child Friendly
                • Air conditioning
                • Private garden

                Price per night from

                $287

                Price per night from

                $287

                Distance approx 16.66 km from Rupert

                  32

                  9 BR Lakefront Luxury Getaway on 10 Acres. Sleeps 24!

                  Green Mountains / Peru

                  Peru house

                  9 24 2 nights min

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

                  Price per night from

                  $859

                  Price per night from

                  $859

                  Distance approx 16.72 km from Rupert

                    8

                    Blue Door Farm Cottage - SKI! Bromley 4mi., Magic 5mI., Stratton 12mi, Okemo..

                    Green Mountains / Peru

                    Peru house

                    2 5 2 nights min

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

                    Price per night from

                    $190

                    Responds fast!
                    avg. 1 hour 40 minutes

                    Price per night from

                    $190

                    Distance approx 8.62 km from Rupert

                      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

                      $373

                      Price per night from

                      $373

                      Distance approx 10.03 km from Rupert

                      (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
                        …see more

                        Price per night from

                        $343

                        Responds fast!
                        avg. 1 hour 48 minutes

                        Price per night from

                        $343

                        Distance approx 7.71 km from Rupert

                          14

                          Maple Lawn Farm, Pawlet, VT

                          Vermont / Pawlet

                          Pawlet house

                          4 14 3 nights min

                          • 4 bedrooms
                          • sleeps 14
                          • 3 nights min
                          • Child Friendly
                          • Air conditioning
                          • Ask about pets

                          Price per night from

                          $458

                          Price per night from

                          $458

                          Distance approx 13.1 km from Rupert

                          (11) Excellent 

                            18

                            Pond Mountain Inn: Garden Cottage

                            Vermont / Wells

                            Wells cottage

                            2 5 2 nights min

                            • 2 bedrooms
                            • sleeps 5
                            • 2 nights min
                            • Nearest beach 6 mi
                            • Ask about children
                            • Air conditioning
                            “Relaxing and cozy” My husband and I stayed here on our honeymoon, and the barn was a great get-away. It was clean, with great high ceilings, nice wood floors, a full kitchen, a nice living room with tv and books. Our host and hostess at the main B&B
                            …see more

                            Price per night from

                            $228

                            Price per night from

                            $228

                            Distance approx 10.84 km from Rupert

                            (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 18.45 km from Rupert

                                13

                                Updated Stratton Townhouse.. Heated Saltwater Pool

                                Vermont / Bondville

                                Bondville apartment

                                3 10 2 nights min

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

                                Price per night from

                                $373

                                Price per night from

                                $373

                                Distance approx 10.27 km from Rupert

                                (2) Excellent 

                                  22

                                  RYE CHALET IN HIDDEN VALLEY. Spectacular views. Vermont's famous fresh air.

                                  Vermont / Wells

                                  Wells chalet

                                  3 10 2 nights min

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

                                  Price per night from

                                  $201

                                  Price per night from

                                  $201

                                  Distance approx 13.1 km from Rupert

                                  (22) Excellent 

                                    17

                                    Pond Mountain Inn: Spacious Suite

                                    Vermont / Wells

                                    Wells apartment

                                    1 4 2 nights min

                                    • 1 bedroom
                                    • sleeps 4
                                    • 2 nights min
                                    • Nearest beach 0 mi
                                    • Child Friendly
                                    • Car not necessary
                                    “Great Experience” Lori and Gary were Great, and very accommodating. The scenery was spectaculur,and the house is beautiful. Food was great and I loved seeing the Hummingbirds at Breakfast. Can't wait to do this again.
                                    …see more

                                    Price per night from

                                    $205

                                    Price per night from

                                    $205

                                    Distance approx 13.15 km from Rupert

                                    (1) Excellent 

                                      25

                                      3 bedroom lakefront home

                                      Vermont / Poultney

                                      Poultney house

                                      3 9 2 nights min

                                      • 3 bedrooms
                                      • sleeps 9
                                      • 2 nights min
                                      • Child Friendly
                                      • Private garden

                                      Price per night from

                                      $229

                                      Price per night from

                                      $229

                                      Distance approx 18.06 km from Rupert

                                        29

                                        Incredible Home Sets Bar for Stratton Views&Luxury

                                        Vermont / Stratton Mountain

                                        Stratton Mountain house

                                        4 12 2 nights min

                                        • 4 bedrooms
                                        • sleeps 12
                                        • 2 nights min
                                        • Ski
                                        • Child Friendly
                                        • Private garden

                                        Price per night from

                                        $916

                                        Responds fast!
                                        avg. 2 hours 45 minutes

                                        Price per night from

                                        $916

                                        Distance approx 16.82 km from Rupert

                                          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 19.35 km from Rupert

                                          (2) Excellent 

                                            22

                                            Charming Vt. Farmhouse with spectacular mt. views. Children welcome

                                            Vermont / Londonderry

                                            Londonderry house

                                            3 6 min stay varies

                                            • 3 bedrooms
                                            • sleeps 6
                                            • min stay varies
                                            • Nearest beach 6 mi
                                            • Child Friendly
                                            • Private garden
                                            “Wonderful Vacation Home” We stayed at the Humphrey's Farmhouse in august and had a great time. The home is very charming, clean and has just about every ammenity you could ask for. The house is at the top of a hill and the views are incredible, espe
                                            …see more

                                            Price per night from

                                            $153

                                            Price per night from

                                            $153

                                            Distance approx 16.72 km from Rupert

                                              14

                                              Rancher's House (Entire House)

                                              New York / Cambridge

                                              Cambridge house

                                              3 6 1 night min

                                              • 3 bedrooms
                                              • sleeps 6
                                              • 1 night min
                                              • Nearest beach 0 mi
                                              • Child Friendly
                                              • Pet Friendly

                                              Price per night from

                                              $102

                                              Price per night from

                                              $102

                                              Distance approx 16.8 km from Rupert

                                                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 19.68 km from Rupert

                                                  24

                                                  Jamaica Townhome w/ Pool - Mins to Stratton Mtn!

                                                  Vermont / Jamaica

                                                  Jamaica house

                                                  2 12 min stay varies

                                                  • 2 bedrooms
                                                  • sleeps 12
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Ski
                                                  • Child Friendly

                                                  Price per night from

                                                  $338

                                                  Responds fast!
                                                  avg. 20 minutes

                                                  Price per night from

                                                  $338

                                                  Distance approx 17.22 km from Rupert

                                                    4

                                                    The I.B. Munson House Inn - Bedroom 3

                                                    Vermont / Wallingford

                                                    Wallingford b and b

                                                    1 2 2 nights min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 2 nights min

                                                    Price per night from

                                                    $224

                                                    Price per night from

                                                    $224

                                                    Distance approx 19.76 km from Rupert

                                                      21

                                                      Log Home w/ first class amenities near OKEMO Mtn

                                                      Vermont / Mount Holly

                                                      Mount Holly log cabin

                                                      5 15 3 nights min

                                                      • 5 bedrooms
                                                      • sleeps 15
                                                      • 3 nights min
                                                      • Beach / lakeside relaxation
                                                      • Nearest beach 12 mi
                                                      • Ski

                                                      Price per night from

                                                      $516

                                                      Price per night from

                                                      $516

                                                      Distance approx 13.28 km from Rupert

                                                        10

                                                        Spectacular 50 miles Year Round Mountain View - 3+ BR Townhouse

                                                        Green Mountains / Peru

                                                        Peru townhouse

                                                        4 8 min stay varies

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

                                                        Price per night from

                                                        $338

                                                        Price per night from

                                                        $338

                                                        Distance approx 10.95 km from Rupert

                                                        (1) Excellent 

                                                          14

                                                          Manchester to Stratton - Taking Inquiries for the Summer Horse Show

                                                          Vermont / Bondville

                                                          Bondville house

                                                          4 8 min stay varies

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

                                                          Price per night from

                                                          $228

                                                          Price per night from

                                                          $228

                                                          Distance approx 17.22 km from Rupert

                                                            4

                                                            The I.B. Munson House Inn - Bedroom 4

                                                            Vermont / Wallingford

                                                            Wallingford b and b

                                                            1 2 2 nights min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 2 nights min

                                                            Price per night from

                                                            $224

                                                            Price per night from

                                                            $224

                                                            Distance approx 17.22 km from Rupert

                                                              4

                                                              The I.B. Munson House Inn - All Bedrooms

                                                              Vermont / Wallingford

                                                              Wallingford b and b

                                                              4 8 2 nights min

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • 2 nights min
                                                              • Air conditioning
                                                              • Private garden

                                                              Price per night from

                                                              $716

                                                              Price per night from

                                                              $716

                                                              Distance approx 11.21 km from Rupert

                                                              (2) Excellent 

                                                                13

                                                                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 12.5 km from Rupert

                                                                  16

                                                                  A Family Place

                                                                  Vermont / Bondville

                                                                  Bondville house

                                                                  5 12 2 nights min

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

                                                                  Price per night from

                                                                  $430

                                                                  Price per night from

                                                                  $430

                                                                  Distance approx 11.22 km from Rupert

                                                                    16

                                                                    5 STAR HOME W/HOT TUB! SKI BROMLEY STRATTON MAGIC!

                                                                    Green Mountains / East Dorset

                                                                    East Dorset house

                                                                    3 9 7 nights min

                                                                    • 3 bedrooms
                                                                    • sleeps 9
                                                                    • 7 nights min
                                                                    • Child Friendly
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $801

                                                                    Price per night from

                                                                    $801

                                                                    Distance approx 16.72 km from Rupert

                                                                      69

                                                                      Weddings Retreats Discovery & Wellness! - The Blue Door Farm Resort

                                                                      Vermont / Landgrove

                                                                      Landgrove house

                                                                      8 22 min stay varies

                                                                      • 8 bedrooms
                                                                      • sleeps 22
                                                                      • min stay varies
                                                                      • Beach / lakeside relaxation
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $781

                                                                      Responds fast!
                                                                      avg. 2 hours 23 minutes

                                                                      Price per night from

                                                                      $781

                                                                      Distance approx 17.22 km from Rupert

                                                                        4

                                                                        The I.B. Munson House Inn - Bedroom 1

                                                                        Vermont / Wallingford

                                                                        Wallingford b and b

                                                                        1 2 2 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 2 nights min

                                                                        Price per night from

                                                                        $224

                                                                        Price per night from

                                                                        $224

                                                                        Distance approx 9.38 km from Rupert

                                                                          18

                                                                          Emerald Lake Club (Lake/Horse Show)

                                                                          Green Mountains / Dorset

                                                                          Dorset house

                                                                          8 23 2 nights min

                                                                          • 8 bedrooms
                                                                          • sleeps 23
                                                                          • 2 nights min
                                                                          • Nearest beach 0.5 mi
                                                                          • Child Friendly
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $161

                                                                          Responds fast!
                                                                          avg. 38 minutes

                                                                          Price per night from

                                                                          $161

                                                                          Distance approx 18.91 km from Rupert

                                                                          (9) Very Good 

                                                                            10

                                                                            Stratton 4 Bedroom Home

                                                                            Vermont / Stratton Mountain

                                                                            Stratton Mountain house

                                                                            4 11 2 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 11
                                                                            • 2 nights min
                                                                            • Ski
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $401

                                                                            Responds fast!
                                                                            avg. 3 hours 1 minutes

                                                                            Price per night from

                                                                            $401

                                                                            Distance approx 19.86 km from Rupert

                                                                              10

                                                                              Ski Southern VT! Perfect home for large groups ... HOT TUB!

                                                                              Vermont / Londonderry

                                                                              Londonderry house

                                                                              5 12 2 nights min

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

                                                                              Price per night from

                                                                              $630

                                                                              Price per night from

                                                                              $630