Rupert Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

96 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

      6 15 min stay varies

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

      Price per night from

      $344

      Responds fast!
      avg. 58 minutes

      Price per night from

      $344

      Great rentals within 20 miles that match your search

      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

        $575

        Price per night from

        $575

        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

          $288

          Price per night from

          $288

          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

            $632

            Price per night from

            $632

            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

              $452

              Price per night from

              $452

              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

                $344

                Responds fast!
                avg. 1 hour 48 minutes

                Price per night from

                $344

                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

                  $191

                  Responds fast!
                  avg. 2 hours 15 minutes

                  Price per night from

                  $191

                  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

                    $229

                    Price per night from

                    $229

                    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

                      $460

                      Price per night from

                      $460

                      Distance approx 5.5 km from Rupert

                      (1) Excellent 

                        4

                        Peaceful setting

                        Green Mountains / Dorset

                        Dorset house

                        3 5 3 nights min

                        • 3 bedrooms
                        • sleeps 5
                        • 3 nights min
                        • Ski
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $300

                        Price per night from

                        $300

                        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

                          $206

                          Price per night from

                          $206

                          Distance approx 13.16 km from Rupert

                            22

                            Slopeside Townhome in Bromley Village

                            Green Mountains / Peru

                            Peru townhouse

                            4 11 2 nights min

                            • 4 bedrooms
                            • sleeps 11
                            • 2 nights min
                            • Child Friendly

                            Price per night from

                            $317

                            Price per night from

                            $317

                            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 18.54 km from Rupert

                                48

                                Ski-in/Ski-out townhome w/five levels of luxury furnishings & private hot tub!

                                Vermont / Stratton Mountain

                                Stratton Mountain house

                                4 6 2 nights min

                                • 4 bedrooms
                                • sleeps 6
                                • 2 nights min
                                • Child Friendly
                                • Car not necessary
                                • Air conditioning

                                Price per night from

                                $640

                                Responds fast!
                                avg. 1 hour 28 minutes

                                Price per night from

                                $640

                                Distance approx 9.66 km from Rupert

                                  24

                                  Manchester Center with a Mountain View /Right in Town!

                                  Green Mountains / Manchester

                                  Manchester house

                                  3 8 2 nights min

                                  • 3 bedrooms
                                  • sleeps 8
                                  • 2 nights min
                                  • Child Friendly
                                  • Air conditioning
                                  • Pet Friendly

                                  Price per night from

                                  $259

                                  Price per night from

                                  $259

                                  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 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

                                      $920

                                      Responds fast!
                                      avg. 2 hours 45 minutes

                                      Price per night from

                                      $920

                                      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 13.35 km from Rupert

                                        (1) Excellent 

                                          43

                                          Trail Side at Bromley Resort Minutes from ManchesterVT, VSF horse show, Stratton

                                          Green Mountains / Peru

                                          Peru house

                                          4 12 2 nights min

                                          • 4 bedrooms
                                          • sleeps 12
                                          • 2 nights min
                                          • Ski
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $259

                                          Responds fast!
                                          avg. 2 hours 53 minutes

                                          Price per night from

                                          $259

                                          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 18.33 km from Rupert

                                            (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

                                              $346

                                              Responds fast!
                                              avg. 3 hours 13 minutes

                                              Price per night from

                                              $346

                                              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

                                                $340

                                                Responds fast!
                                                avg. 21 minutes

                                                Price per night from

                                                $340

                                                Distance approx 11.79 km from Rupert

                                                  24

                                                  Butternut Hill Unit #11

                                                  Vermont / Wells

                                                  Wells apartment

                                                  2 4 7 nights min

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

                                                  Price per night from

                                                  $115

                                                  Price per night from

                                                  $115

                                                  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

                                                    $517

                                                    Price per night from

                                                    $517

                                                    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 4.6 km from Rupert

                                                        14

                                                        The Musser House on the Dorset Green

                                                        Green Mountains / Dorset

                                                        Dorset house

                                                        6 16 2 nights min

                                                        • 6 bedrooms
                                                        • sleeps 16
                                                        • 2 nights min
                                                        • Child Friendly

                                                        Price per night from

                                                        $806

                                                        Price per night from

                                                        $806

                                                        Distance approx 9.38 km from Rupert

                                                          32

                                                          Private Home w/ Views - Near Manchester Golf & Ski

                                                          Green Mountains / Dorset

                                                          Dorset house

                                                          5 12 min stay varies

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

                                                          Price per night from

                                                          $547

                                                          Responds fast!
                                                          avg. 21 minutes

                                                          Price per night from

                                                          $547

                                                          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

                                                            $719

                                                            Price per night from

                                                            $719

                                                            Distance approx 16.27 km from Rupert

                                                            (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 5.6 km from Rupert

                                                                15

                                                                Myrick View House

                                                                Green Mountains / Dorset

                                                                Dorset house

                                                                3 6 14 nights min

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

                                                                Price per night from

                                                                $248

                                                                Price per night from

                                                                $248

                                                                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

                                                                  $431

                                                                  Price per night from

                                                                  $431

                                                                  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

                                                                    $784

                                                                    Responds fast!
                                                                    avg. 2 hours 15 minutes

                                                                    Price per night from

                                                                    $784

                                                                    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

                                                                      $804

                                                                      Price per night from

                                                                      $804

                                                                      Distance approx 16.33 km from Rupert

                                                                        14

                                                                        NEW LISTING!Cozy Ski Chalet near 4 Ski Mountains.

                                                                        Green Mountains / Peru

                                                                        Peru chalet

                                                                        3 8 3 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 8
                                                                        • 3 nights min
                                                                        • Child Friendly
                                                                        • Air conditioning
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $218

                                                                        Price per night from

                                                                        $218

                                                                        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

                                                                          $223

                                                                          Price per night from

                                                                          $223

                                                                          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 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

                                                                              $632

                                                                              Price per night from

                                                                              $632