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66 Houses

(178) Excellent 

    37

    Unique People & Pet-Welcoming Country Haven

    Berkshires / Charlemont

    Charlemont apartment

    1 4 2 nights min

    • 1 bedroom
    • sleeps 4
    • 2 nights min
    • Child Friendly
    • Air conditioning
    • Pet Friendly
    “Cozy little spot, kid and definitely dog friendly” We brought our Cavalier with us and had a great time at the cottage. It was clean and gave us tons of room. Would definitely stay again.

    Price per night from

    $149

    Price per night from

    $149

    Great rentals within 20 miles that match your search

    Distance approx 16.34 km from Charlemont

      18

      Historic Home on 8.5 Acres

      Berkshires / Dalton

      Dalton house

      3 9 3 nights min

      • 3 bedrooms
      • sleeps 9
      • 3 nights min
      • Swimming pool
      • Child Friendly
      • Air conditioning

      Price per night from

      $458

      Price per night from

      $458

      Distance approx 13.66 km from Charlemont

        14

        ROOM walking distance to Mass MoCa

        Berkshires / North Adams

        North Adams apartment

        1 8 min stay varies

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

        Price per night from

        $115

        Price per night from

        $115

        Distance approx 13.63 km from Charlemont

        (2) Excellent 

          41

          Apartment walking distance to Mass MoCa!!

          Berkshires / North Adams

          North Adams apartment

          2 10 min stay varies

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

          Price per night from

          $200

          Price per night from

          $200

          Distance approx 18.75 km from Charlemont

            24

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

            Vermont / Wilmington

            Wilmington house

            4 12 7 nights min

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

            Price per night from

            $246

            Responds fast!
            avg. 19 minutes

            Price per night from

            $246

            Distance approx 19.22 km from Charlemont

              28

              The Little Farmhouse at Adams Farm

              Vermont / Wilmington

              Wilmington house

              3 6 2 nights min

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

              Price per night from

              $258

              Price per night from

              $258

              Distance approx 13.4 km from Charlemont

                37

                3 BR apartment, walking distance to Mass MoCa

                Berkshires / North Adams

                North Adams apartment

                3 15 min stay varies

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

                Price per night from

                $212

                Price per night from

                $212

                Distance approx 15.43 km from Charlemont

                  21

                  New Lakefront Cedar Log Home

                  Vermont / Wilmington

                  Wilmington chalet

                  3 12 2 nights min

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

                  Price per night from

                  $515

                  Responds fast!
                  avg. 1 hour 43 minutes

                  Price per night from

                  $515

                  Distance approx 18.06 km from Charlemont

                    17

                    House On Main Street

                    Berkshires / Williamstown

                    Williamstown house

                    4 16 2 nights min

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

                    Price per night from

                    $572

                    Responds fast!
                    avg. 1 hour 19 minutes

                    Price per night from

                    $572

                    Distance approx 13.8 km from Charlemont

                    (7) Excellent 

                      5

                      Vermont Log Cabin available for weekend and weekly

                      Vermont / Guilford

                      Guilford log cabin

                      2 5 2 nights min

                      • 2 bedrooms
                      • sleeps 5
                      • 2 nights min
                      • Pet Friendly
                      “Hidden Gem” My boyfriend and I had the pleasure of staying at this beautiful cabin a couple of weeks ago and honestly, I can't say enough good things about it! For starters, it is gorgeous both inside and out and much bigger than we had anticipated.

                      Price per night from

                      $126

                      Price per night from

                      $126

                      Distance approx 17.81 km from Charlemont

                      (1) Very Good 

                        13

                        Mount Snow Area Home with 5 Bedrooms

                        Vermont / Wilmington

                        Wilmington house

                        5 12 2 nights min

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

                        Price per night from

                        $343

                        Price per night from

                        $343

                        Distance approx 12.36 km from Charlemont

                          38

                          Nestled in the Berkshire Hills, The Manor ensures a joyous experience!

                          Berkshires / Adams

                          Adams house

                          7 14 2 nights min

                          • 7 bedrooms
                          • sleeps 14
                          • 2 nights min
                          • Child Friendly
                          • Private garden

                          Price per night from

                          $458

                          Price per night from

                          $458

                          Distance approx 15.92 km from Charlemont

                            19

                            Charming Berkshires lakefront house, great views

                            Berkshires / Cheshire

                            Cheshire house

                            2 5 min stay varies

                            • 2 bedrooms
                            • sleeps 5
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Child Friendly
                            • Car not necessary

                            Price per night from

                            $286

                            Price per night from

                            $286

                            Distance approx 11.98 km from Charlemont

                            (1) Excellent 

                              7

                              PARADISE on EARTH! - Historic 4BR Farmhouse

                              Vermont / West Halifax

                              West Halifax house

                              4 8 3 nights min

                              • 4 bedrooms
                              • sleeps 8
                              • 3 nights min
                              • Child Friendly
                              • Ask about pets
                              • Private garden

                              Price per night from

                              $326

                              Price per night from

                              $326

                              Distance approx 13.32 km from Charlemont

                              (4) Excellent 

                                16

                                Lakefront Summer Vacation Cottages

                                Hampshire County / Goshen

                                Goshen cottage

                                3 6 7 nights min

                                • 3 bedrooms
                                • sleeps 6
                                • 7 nights min
                                • Beach / lakeside relaxation
                                • Child Friendly
                                • Pet Friendly

                                Price per night from

                                $195

                                Price per night from

                                $195

                                Distance approx 6.2 km from Charlemont

                                (7) Excellent 

                                  6

                                  Retreat in the Woods

                                  Berkshires / Savoy

                                  Savoy house

                                  2 4 2 nights min

                                  • 2 bedrooms
                                  • sleeps 4
                                  • 2 nights min
                                  • Suitable for children age 5+

                                  Price per night from

                                  $229

                                  Price per night from

                                  $229

                                  Distance approx 16.81 km from Charlemont

                                    23

                                    Lakeside Year Round Totally Renovated Home

                                    Vermont / Wilmington

                                    Wilmington house

                                    5 10 2 nights min

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

                                    Price per night from

                                    $686

                                    Price per night from

                                    $686

                                    Distance approx 3.86 km from Charlemont Show on Map

                                    (9) Very Good 

                                      22

                                      Flight's End-A Country Home with Babbling Brook

                                      Massachusetts / Hawley

                                      Hawley house

                                      3 8 2 nights min

                                      • 3 bedrooms
                                      • sleeps 8
                                      • 2 nights min
                                      • Child Friendly
                                      • Pet Friendly
                                      “Perfect getaway” We spent few days there. It is very quiet and private. We loved the retro look. Looking forward going there again. It was New Year's eve we were hoping for.

                                      Price per night from

                                      $172

                                      Responds fast!
                                      avg. 2 hours 35 minutes

                                      Price per night from

                                      $172

                                      Distance approx 13.76 km from Charlemont

                                        38

                                        'John's Farmhouse in Mount Snow' on 120 Acres!

                                        Vermont / Whitingham

                                        Whitingham house

                                        5 10 min stay varies

                                        • 5 bedrooms
                                        • sleeps 10
                                        • min stay varies
                                        • Ski
                                        • Child Friendly
                                        • Pet Friendly

                                        Price per night from

                                        $344

                                        Responds fast!
                                        avg. 41 minutes

                                        Price per night from

                                        $344

                                        Distance approx 8.75 km from Charlemont

                                        (8) Excellent 

                                          7

                                          Berkshire Getaway

                                          Berkshires / North Adams

                                          North Adams cottage

                                          2 4 1 night min

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

                                          Price per night from

                                          $172

                                          Price per night from

                                          $172

                                          Distance approx 18.26 km from Charlemont

                                          (5) Excellent 

                                            31

                                            Berkshires Waterfront Lakehouse Sanctuary

                                            Berkshires / Lanesboro

                                            Lanesboro house

                                            3 6 2 nights min

                                            • 3 bedrooms
                                            • sleeps 6
                                            • 2 nights min
                                            • Beach / lakeside relaxation
                                            • Child Friendly
                                            • Air conditioning

                                            Price per night from

                                            $224

                                            Responds fast!
                                            avg. 3 hours 20 minutes

                                            Price per night from

                                            $224

                                            Distance approx 16.69 km from Charlemont

                                              37

                                              Spacious Wilmington Home w/ Game Room & Deck!

                                              Vermont / Wilmington

                                              Wilmington house

                                              6 22 min stay varies

                                              • 6 bedrooms
                                              • sleeps 22
                                              • min stay varies
                                              • Ski
                                              • Child Friendly

                                              Price per night from

                                              $172

                                              Responds fast!
                                              avg. 32 minutes

                                              Price per night from

                                              $172

                                              Distance approx 19.4 km from Charlemont

                                                26

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

                                                Vermont / Wilmington

                                                Wilmington house

                                                5 12 min stay varies

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

                                                Price per night from

                                                $338

                                                Responds fast!
                                                avg. 32 minutes

                                                Price per night from

                                                $338

                                                Distance approx 10.43 km from Charlemont Show on Map

                                                  26

                                                  Serene Shelburne Studio Cabin w/Spring-Fed Pool!

                                                  Massachusetts / Shelburne Falls

                                                  Shelburne Falls studio

                                                  Studio 6 min stay varies

                                                  • Studio
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Ski
                                                  • Child Friendly

                                                  Price per night from

                                                  $189

                                                  Responds fast!
                                                  avg. 41 minutes

                                                  Price per night from

                                                  $189

                                                  Distance approx 18.39 km from Charlemont

                                                    19

                                                    Beautiful Ski/Golf Chalet on Hermitage Club golf course

                                                    Vermont / Wilmington

                                                    Wilmington house

                                                    4 11 2 nights min

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

                                                    Price per night from

                                                    $287

                                                    Price per night from

                                                    $287

                                                    Distance approx 18.55 km from Charlemont

                                                      24

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

                                                      Vermont / Wilmington

                                                      Wilmington log cabin

                                                      2 6 min stay varies

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

                                                      Price per night from

                                                      $155

                                                      Responds fast!
                                                      avg. 32 minutes

                                                      Price per night from

                                                      $155

                                                      Distance approx 17.32 km from Charlemont

                                                        17

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

                                                        Vermont / Wilmington

                                                        Wilmington chalet

                                                        6 15 2 nights min

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

                                                        Price per night from

                                                        $367

                                                        Price per night from

                                                        $367

                                                        Distance approx 16.26 km from Charlemont

                                                          8

                                                          New Timberframe House Rental in the Berkshire Mountains, Masschusetts

                                                          Berkshires / Hinsdale

                                                          Hinsdale house

                                                          3 6 2 nights min

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

                                                          Price per night from

                                                          $166

                                                          Price per night from

                                                          $166

                                                          Distance approx 12.21 km from Charlemont

                                                            11

                                                            OWL'S NEST LODGING

                                                            Massachusetts / Conway

                                                            Conway apartment

                                                            1 3 1 night min

                                                            • 1 bedroom
                                                            • sleeps 3
                                                            • 1 night min
                                                            • Beach / lakeside relaxation
                                                            • Ski
                                                            • Suitable for children age 5+

                                                            Price per night from

                                                            $189

                                                            Price per night from

                                                            $189

                                                            Distance approx 6.97 km from Charlemont Show on Map

                                                            (9) Excellent 

                                                              11

                                                              Charming Affordable Home for groups up to 14

                                                              Massachusetts / Shelburne Falls

                                                              Shelburne Falls house

                                                              7 14 2 nights min

                                                              • 7 bedrooms
                                                              • sleeps 14
                                                              • 2 nights min
                                                              • Ask about children
                                                              • Car not necessary
                                                              • Ask about pets
                                                              “Beautiful house in beautiful village!” Thank you for the use of your beautiful house. It was perfect for our wedding weekend. Everyone was very comfortable and had a great time. Looking forward to coming back again in the future.

                                                              Price per night from

                                                              $573

                                                              Responds fast!
                                                              avg. 1 hour 28 minutes

                                                              Price per night from

                                                              $573

                                                              Distance approx 17.25 km from Charlemont

                                                                24

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

                                                                Vermont / Wilmington

                                                                Wilmington house

                                                                3 10 min stay varies

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

                                                                Price per night from

                                                                $189

                                                                Responds fast!
                                                                avg. 32 minutes

                                                                Price per night from

                                                                $189

                                                                Distance approx 15.71 km from Charlemont

                                                                  24

                                                                  Rustic Goshen Cabin w/ Fire Pit, BBQ & Great Deck!

                                                                  Hampshire County / Goshen

                                                                  Goshen log cabin

                                                                  2 8 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 8
                                                                  • min stay varies
                                                                  • Child Friendly
                                                                  • Air conditioning
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $241

                                                                  Responds fast!
                                                                  avg. 2 hours 49 minutes

                                                                  Price per night from

                                                                  $241

                                                                  Distance approx 14.79 km from Charlemont

                                                                    18

                                                                    Penthouse at Brandt House B&B

                                                                    Massachusetts / Greenfield

                                                                    Greenfield b and b

                                                                    1 4 2 nights min

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

                                                                    Price per night from

                                                                    $286

                                                                    Price per night from

                                                                    $286

                                                                    Distance approx 19.64 km from Charlemont

                                                                      26

                                                                      NEW! Family Home w/Game Room - 3 Mi to Jiminy Peak

                                                                      Berkshires / Hancock

                                                                      Hancock house

                                                                      4 20 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 20
                                                                      • min stay varies
                                                                      • Ski
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $287

                                                                      Responds fast!
                                                                      avg. 18 minutes

                                                                      Price per night from

                                                                      $287

                                                                      Distance approx 11.87 km from Charlemont

                                                                      (1) Excellent 

                                                                        21

                                                                        Lake House in Berkshires

                                                                        Berkshires / North Adams

                                                                        North Adams cottage

                                                                        1 2 2 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 2 nights min

                                                                        Price per night from

                                                                        $121

                                                                        Responds fast!
                                                                        avg. 1 hour 18 minutes

                                                                        Price per night from

                                                                        $121

                                                                        Distance approx 18.1 km from Charlemont

                                                                          9

                                                                          Cozy farmhouse, walk to campus & town

                                                                          Berkshires / Williamstown

                                                                          Williamstown house

                                                                          2 5 2 nights min

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

                                                                          Price per night from

                                                                          $361

                                                                          Price per night from

                                                                          $361

                                                                          Distance approx 12.88 km from Charlemont

                                                                            37

                                                                            Meadowhurst Farm- Queen Rm 1.6 Miles from Mass MoCA

                                                                            Berkshires / Clarksburg

                                                                            Clarksburg room

                                                                            1 2 1 night min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 1 night min
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $81

                                                                            Price per night from

                                                                            $81

                                                                            Distance approx 17.29 km from Charlemont

                                                                              10

                                                                              #B16: 15 West Rd B016-01

                                                                              Vermont / Wilmington

                                                                              Wilmington log cabin

                                                                              2 10 2 nights min

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

                                                                              Price per night from

                                                                              $275

                                                                              Price per night from

                                                                              $275