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177 Houses

(1) Very Good 

    10

    Hugging Bear Inn - Tower Room

    Vermont / Chester

    Chester b and b

    1 2 1 night min

    • 1 bedroom
    • sleeps 2
    • 1 night min
    • Nearest beach 19 mi
    • Child Friendly
    • Air conditioning

    Price per night from

    $137

    Price per night from

    $137

      10

      Hugging Bear Inn - Bear Cub Room

      Vermont / Chester

      Chester b and b

      1 4 1 night min

      • 1 bedroom
      • sleeps 4
      • 1 night min
      • Child Friendly
      • Air conditioning

      Price per night from

      $160

      Price per night from

      $160

        22

        Amare Guesthouse, renovated in-town victorian

        Vermont / Chester

        Chester house

        3 6 2 nights min

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

        Price per night from

        $264

        Price per night from

        $264

          11

          Hugging Bear Inn - Bear's Den Room

          Vermont / Chester

          Chester b and b

          1 5 1 night min

          • 1 bedroom
          • sleeps 5
          • 1 night min
          • Child Friendly
          • Air conditioning

          Price per night from

          $160

          Price per night from

          $160

            30

            Hugging Bear Inn & Shoppe- rent entire Inn

            Vermont / Chester

            Chester b and b

            6 18 1 night min

            • 6 bedrooms
            • sleeps 18
            • 1 night min
            • Nearest beach 19 mi
            • Child Friendly
            • Air conditioning

            Price per night from

            $676

            Price per night from

            $676

              19

              Historic 1868 Carriage House at Chester Depot

              Vermont / Chester

              Chester guest house

              3 6 2 nights min

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

              Price per night from

              $172

              Price per night from

              $172

                24

                Chester House Just 12 Mins to Magic Mtn Ski Area!

                Vermont / Chester

                Chester house

                5 8 min stay varies

                • 5 bedrooms
                • sleeps 8
                • min stay varies
                • Ski
                • Child Friendly
                • Pet Friendly

                Price per night from

                $155

                Responds fast!
                avg. 8 minutes

                Price per night from

                $155

                  10

                  The 1843 Stone House - Chester, VT (3bdrm/ 2 ba)

                  Vermont / Chester

                  Chester house

                  3 8 2 nights min

                  • 3 bedrooms
                  • sleeps 8
                  • 2 nights min
                  • Child Friendly

                  Price per night from

                  $201

                  Price per night from

                  $201

                  Great rentals within 20 miles that match your search

                  Distance approx 13.75 km from Chester

                    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 13.97 km from Chester

                      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 19.47 km from Chester

                        25

                        Upper unit of Chalet, minutes to Killington, Okemo or Woodstock

                        Vermont / Plymouth

                        Plymouth house

                        2 6 2 nights min

                        • 2 bedrooms
                        • sleeps 6
                        • 2 nights min
                        • Nearest beach 1 mi
                        • Child Friendly
                        • Pet Friendly

                        Price per night from

                        $403

                        Price per night from

                        $403

                        Distance approx 16.86 km from Chester

                        (4) Excellent 

                          55

                          Reading Farms Estate/ Vermont Luxury Rental

                          Vermont / Reading

                          Reading villa

                          15 44 min stay varies

                          • 15 bedrooms
                          • sleeps 44
                          • min stay varies
                          • Swimming pool
                          • Child Friendly
                          • Ask about pets

                          Price per night from

                          $2,815

                          Price per night from

                          $2,815

                          Distance approx 15.13 km from Chester

                          (2) Excellent 

                            32

                            Cozy mtn. COTTAGE - ski, swim, hike, foliage -- Family Fun or Romantic Getaway

                            Vermont / Belmont

                            Belmont house

                            2 6 min stay varies

                            • 2 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Nearest beach 2 mi
                            • Child Friendly

                            Price per night from

                            $149

                            Responds fast!
                            avg. 35 minutes

                            Price per night from

                            $149

                            Distance approx 12.97 km from Chester

                            (2) Excellent 

                              11

                              Ski-in/out Luxury 3 Bedroom & 3 Bathroom Okemo Penthouse Condo at Jackson Gore

                              Vermont / Ludlow

                              Ludlow apartment

                              4 10 2 nights min

                              • 4 bedrooms
                              • sleeps 10
                              • 2 nights min
                              • Swimming pool
                              • Ski
                              • Child Friendly

                              Price per night from

                              $1,490

                              Price per night from

                              $1,490

                              Distance approx 15.45 km from Chester

                              (2) Excellent 

                                21

                                3 Season Cabin - sleeping porch lake trails playground

                                Vermont / Mount Holly

                                Mount Holly log cabin

                                3 8 2 nights min

                                • 3 bedrooms
                                • sleeps 8
                                • 2 nights min
                                • Beach / lakeside relaxation
                                • Child Friendly
                                • Pet Friendly

                                Price per night from

                                $103

                                Price per night from

                                $103

                                Distance approx 13.66 km from Chester

                                (1) Excellent 

                                  12

                                  Charming and cozy Log cabin near Stratton Vermont

                                  Vermont / Jamaica

                                  Jamaica house

                                  4 6 2 nights min

                                  • 4 bedrooms
                                  • sleeps 6
                                  • 2 nights min
                                  • Child Friendly
                                  • Pet Friendly
                                  • Private garden

                                  Price per night from

                                  $345

                                  Responds fast!
                                  avg. 1 hour 28 minutes

                                  Price per night from

                                  $345

                                  Distance approx 19.09 km from Chester

                                    17

                                    **Spectacular Green Mtn Natl Forest Retreat **

                                    Green Mountains / Manchester

                                    Manchester log cabin

                                    5 10 7 nights min

                                    • 5 bedrooms
                                    • sleeps 10
                                    • 7 nights min
                                    • Child Friendly
                                    • Car not necessary
                                    • Private garden

                                    Price per night from

                                    $573

                                    Price per night from

                                    $573

                                    Distance approx 18.26 km from Chester

                                      24

                                      Rustic Peru Townhome w/Deck - 30 Yards From Slopes

                                      Green Mountains / Peru

                                      Peru house

                                      3 11 min stay varies

                                      • 3 bedrooms
                                      • sleeps 11
                                      • min stay varies
                                      • Swimming pool
                                      • Ski
                                      • Child Friendly

                                      Price per night from

                                      $287

                                      Responds fast!
                                      avg. 58 minutes

                                      Price per night from

                                      $287

                                      Distance approx 11.67 km from Chester

                                      (1) Excellent 

                                        29

                                        Walk to ski trials on Okemo! Private Luxury Chalet

                                        Vermont / Ludlow

                                        Ludlow chalet

                                        5 14 3 nights min

                                        • 5 bedrooms
                                        • sleeps 14
                                        • 3 nights min
                                        • Child Friendly

                                        Price per night from

                                        $567

                                        Responds fast!
                                        avg. 1 hour 40 minutes

                                        Price per night from

                                        $567

                                        Distance approx 11.65 km from Chester

                                          16

                                          Okemo Slopeside Rental located at the Main Base!

                                          Vermont / Ludlow

                                          Ludlow condo

                                          1 2 2 nights min

                                          • 1 bedroom
                                          • sleeps 2
                                          • 2 nights min
                                          • Ski
                                          • Child Friendly

                                          Price per night from

                                          $431

                                          Price per night from

                                          $431

                                          Distance approx 17.17 km from Chester

                                          (1) Excellent 

                                            11

                                            3 bedroom lake home on Crescent lake

                                            New Hampshire / Newport

                                            Newport house

                                            3 7 2 nights min

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

                                            Price per night from

                                            $216

                                            Price per night from

                                            $216

                                            Distance approx 10.9 km from Chester Show on Map

                                            (5) Excellent 

                                            Certificate of Excellence

                                              17

                                              Oma"s Kottage

                                              Vermont / Ludlow

                                              Ludlow house

                                              6 11 2 nights min

                                              • 6 bedrooms
                                              • sleeps 11
                                              • 2 nights min
                                              • Nearest beach 6 mi
                                              • Ski
                                              • Child Friendly

                                              Certificate of Excellence

                                              Price per night from

                                              $229

                                              Responds fast!
                                              avg. 1 hour 41 minutes

                                              Price per night from

                                              $229

                                              Distance approx 19.59 km from Chester

                                              (2) Very Good 

                                                19

                                                Kassmel's Mountain Haus

                                                Vermont / West Wardsboro

                                                West Wardsboro house

                                                4 8 2 nights min

                                                • 4 bedrooms
                                                • sleeps 8
                                                • 2 nights min
                                                • Swimming pool
                                                • Child Friendly
                                                • Private garden

                                                Price per night from

                                                $344

                                                Responds fast!
                                                avg. 3 hours 36 minutes

                                                Price per night from

                                                $344

                                                Distance approx 15.17 km from Chester

                                                  8

                                                  Lakefront vacation home - 4 BR - sleeps 10

                                                  Vermont / Ludlow

                                                  Ludlow house

                                                  4 10 3 nights min

                                                  • 4 bedrooms
                                                  • sleeps 10
                                                  • 3 nights min
                                                  • Child Friendly
                                                  • Private garden

                                                  Price per night from

                                                  $288

                                                  Price per night from

                                                  $288

                                                  Distance approx 8.81 km from Chester Show on Map

                                                    8

                                                    Okemo Ski Get Away on Free Okemo Shuttle Route

                                                    Vermont / Proctorsville

                                                    Proctorsville house

                                                    3 10 2 nights min

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

                                                    Price per night from

                                                    $232

                                                    Price per night from

                                                    $232

                                                    Distance approx 12.02 km from Chester

                                                      16

                                                      Fox Run -- Sleeps 10 - 12, Only 1 mile from Okemo Jackson Gore Base

                                                      Vermont / Ludlow

                                                      Ludlow townhouse

                                                      4 12 2 nights min

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

                                                      Price per night from

                                                      $460

                                                      Price per night from

                                                      $460

                                                      Distance approx 10.87 km from Chester Show on Map

                                                        14

                                                        Clean, Cozy and Centrally located 3 BR Townhouse

                                                        Vermont / Ludlow

                                                        Ludlow house

                                                        3 10 3 nights min

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

                                                        Price per night from

                                                        $144

                                                        Responds fast!
                                                        avg. 2 hours 55 minutes

                                                        Price per night from

                                                        $144

                                                        Distance approx 14.76 km from Chester

                                                          25

                                                          Luxury Lakefront Home near Okemo

                                                          Vermont / Ludlow

                                                          Ludlow house

                                                          3 8 7 nights min

                                                          • 3 bedrooms
                                                          • sleeps 8
                                                          • 7 nights min
                                                          • Beach / lakeside relaxation
                                                          • Ski
                                                          • Child Friendly

                                                          Price per night from

                                                          $742

                                                          Price per night from

                                                          $742

                                                          Distance approx 8.26 km from Chester Show on Map

                                                            28

                                                            Renovated 1950's Farmhouse on 300 Acres in Grafton

                                                            Vermont / Grafton

                                                            Grafton house

                                                            3 8 min stay varies

                                                            • 3 bedrooms
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $287

                                                            Responds fast!
                                                            avg. 8 minutes

                                                            Price per night from

                                                            $287

                                                            Distance approx 18.79 km from Chester

                                                            (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 6.16 km from Chester Show on Map

                                                                28

                                                                Chester Farmhouse on 100 Acres, 15 Min to Okemo!

                                                                Vermont / Proctorsville

                                                                Proctorsville house

                                                                5 14 min stay varies

                                                                • 5 bedrooms
                                                                • sleeps 14
                                                                • min stay varies
                                                                • Ski
                                                                • Child Friendly
                                                                • Pet Friendly

                                                                Price per night from

                                                                $288

                                                                Responds fast!
                                                                avg. 58 minutes

                                                                Price per night from

                                                                $288

                                                                Distance approx 10.86 km from Chester Show on Map

                                                                  16

                                                                  Quiet Hillside 4 Bedroom Carriage House W/3 Baths

                                                                  Vermont / Ludlow

                                                                  Ludlow guest house

                                                                  5 10 2 nights min

                                                                  • 5 bedrooms
                                                                  • sleeps 10
                                                                  • 2 nights min
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $346

                                                                  Price per night from

                                                                  $346

                                                                  Distance approx 16.98 km from Chester

                                                                    24

                                                                    Vermont Cottage Lake Amherst

                                                                    Vermont / Plymouth

                                                                    Plymouth cottage

                                                                    5 12 2 nights min

                                                                    • 5 bedrooms
                                                                    • sleeps 12
                                                                    • 2 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Child Friendly
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $802

                                                                    Price per night from

                                                                    $802

                                                                    Distance approx 10.38 km from Chester Show on Map

                                                                      28

                                                                      The Apple Knoll Cottages at Weston - Skiing, Theatre, Craft Brews, & Farm Foods!

                                                                      Vermont / Weston

                                                                      Weston house

                                                                      1 4 2 nights min

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

                                                                      Price per night from

                                                                      $171

                                                                      Responds fast!
                                                                      avg. 2 hours 15 minutes

                                                                      Price per night from

                                                                      $171

                                                                      Distance approx 15.44 km from Chester

                                                                        20

                                                                        Cabin in the Big Woods - sleeping porch lake trails playground

                                                                        Vermont / Mount Holly

                                                                        Mount Holly log cabin

                                                                        1 6 2 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 6
                                                                        • 2 nights min
                                                                        • Child Friendly
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $92

                                                                        Price per night from

                                                                        $92

                                                                        Distance approx 10.78 km from Chester Show on Map

                                                                          12

                                                                          Ski Country, close to VAST, Snowshoeing, XC, etc.

                                                                          Vermont / Weston

                                                                          Weston house

                                                                          4 8 2 nights min

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • 2 nights min
                                                                          • Child Friendly
                                                                          • Pet Friendly
                                                                          • Private garden

                                                                          Price per night from

                                                                          $172

                                                                          Price per night from

                                                                          $172

                                                                          Distance approx 14.75 km from Chester

                                                                            27

                                                                            NEW! 'Green Mountain Escape'-Near Stratton Resort!

                                                                            Vermont / Jamaica

                                                                            Jamaica house

                                                                            4 11 min stay varies

                                                                            • 4 bedrooms
                                                                            • sleeps 11
                                                                            • min stay varies
                                                                            • Ski
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $304

                                                                            Responds fast!
                                                                            avg. 58 minutes

                                                                            Price per night from

                                                                            $304

                                                                            Distance approx 11.45 km from Chester Show on Map

                                                                            (2) Excellent 

                                                                              25

                                                                              Walk to Okemo Ski Lifts! Private 5 bedroom home.

                                                                              Vermont / Ludlow

                                                                              Ludlow house

                                                                              5 13 min stay varies

                                                                              • 5 bedrooms
                                                                              • sleeps 13
                                                                              • min stay varies
                                                                              • Nearest beach 3 mi
                                                                              • Swimming pool
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $287

                                                                              Responds fast!
                                                                              avg. 2 hours 18 minutes

                                                                              Price per night from

                                                                              $287

                                                                              About Chester

                                                                              For scenic beauty in the middle of a vibrant and historic area, consider Chester for your next vacation destination! Most of the shops and restaurants throughout Chester can be found along Main Street, but the town is small enough that anything you wish to reach can be accessed by foot.

                                                                              While you're in Chester, be sure to also make time for these destinations that highlight the rich history and beautiful scenery of the area:

                                                                              • Chester Historical Society: Learn more about the town's proud history with the exhibits and artifacts found at this long-standing museum.
                                                                              • Chester Vietnam Conflict Monument: Located in the middle of downtown, this monument is dedicated to the men and women in Chester who served in the Vietnam War.
                                                                              • Play Golf: Tater Hill Golf Club is a nine-hole course that provides an afternoon of fun for all ages and skill levels.
                                                                              • Go Skiing: Nearby Okemo Mountain is considered one of the premier destinations for skiing in the entire country.

                                                                              There are great events in Chester throughout the year, ranging from live performance to parties that stretch across town. Watch chainsaw carvers show off their skills at the Big Buzz Chainsaw Carving Festival in October, sample the works of over 60 local craftsmen and artisans at Chester's Fall Craft Fair in September, or watch dozens of hot air balloons soar through the sky at the Quechee Vermont Balloon Festival in May.

                                                                              Whether you're looking for a picturesque condo or apartment just steps from the outdoor recreational options throughout town, or a cozy cabin with mountain views, there's a vacation rental that will put you exactly where you want to be in Chester.

                                                                              If you're looking to explore the rest of Vermont, Chester is a great location to use as a base for a series of day trips. The big city of Burlington and the outdoor attractions of Stowe can both be reached within an hour by car.