Readsboro Rentals

Close

Enter dates for more accurate prices

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

98 Houses

Great rentals within 20 miles that match your search

Distance approx 14.13 km from Readsboro

    0

    Classic, dog-friendly cabin in the woods w/ private deck

    Vermont / Dover

    Dover house

    3 10 min stay varies

    • 3 bedrooms
    • sleeps 10
    • min stay varies
    • Child Friendly
    • Car not necessary
    • Pet Friendly

    Price per night from

    $124

    Responds fast!
    avg. 3 hours 3 minutes

    Price per night from

    $124

    Distance approx 6.13 km from Readsboro Show on Map

      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

      $343

      Responds fast!
      avg. 41 minutes

      Price per night from

      $343

      Distance approx 7.97 km from Readsboro Show on Map

        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. 16 minutes

        Price per night from

        $172

        Distance approx 8.36 km from Readsboro Show on Map

          10

          #C184: 49 Low Land Loop C184-03

          Vermont / Wilmington

          Wilmington villa

          3 8 2 nights min

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

          Price per night from

          $413

          Price per night from

          $413

          Distance approx 8.36 km from Readsboro Show on Map

            32

            NEW LISTING! Eclectic & art-filled home w/stunning mountain view & master suite

            Vermont / Wilmington

            Wilmington house

            4 10 2 nights min

            • 4 bedrooms
            • sleeps 10
            • 2 nights min
            • Child Friendly
            • Car not necessary

            Price per night from

            $124

            Price per night from

            $124

            Distance approx 7.7 km from Readsboro Show on Map

              10

              #84: 18 Spring Court 084-01

              Vermont / Wilmington

              Wilmington villa

              3 6 2 nights min

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

              Price per night from

              $275

              Price per night from

              $275

              Distance approx 7.7 km from Readsboro Show on Map

                10

                #627: 31 Howes Loop 627-02

                Vermont / Wilmington

                Wilmington villa

                5 12 2 nights min

                • 5 bedrooms
                • sleeps 12
                • 2 nights min
                • Ask about children
                • Ask about pets

                Price per night from

                $722

                Price per night from

                $722

                Distance approx 12.53 km from Readsboro

                (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

                  Distance approx 7.7 km from Readsboro Show on Map

                    10

                    #B109: 19 View Road B109-04

                    Vermont / Wilmington

                    Wilmington villa

                    3 7 2 nights min

                    • 3 bedrooms
                    • sleeps 7
                    • 2 nights min
                    • Ask about children
                    • Pet Friendly

                    Price per night from

                    $172

                    Price per night from

                    $172

                    Distance approx 15.6 km from Readsboro

                    (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

                      $571

                      Responds fast!
                      avg. 1 hour 28 minutes

                      Price per night from

                      $571

                      Distance approx 13.46 km from Readsboro

                      (2) Excellent 

                        0

                        Ski-in/ski-out condo with shared pool, hot tub & sauna - great location!

                        Vermont / Dover

                        Dover house

                        3 10 min stay varies

                        • 3 bedrooms
                        • sleeps 10
                        • min stay varies
                        • Swimming pool
                        • Child Friendly
                        • Car not necessary

                        Price per night from

                        $113

                        Responds fast!
                        avg. 3 hours 3 minutes

                        Price per night from

                        $113

                        Distance approx 7.7 km from Readsboro Show on Map

                          10

                          #C230: 129 East Brook Crossing C230-03

                          Vermont / Wilmington

                          Wilmington villa

                          3 7 2 nights min

                          • 3 bedrooms
                          • sleeps 7
                          • 2 nights min
                          • Ask about children
                          • Pet Friendly

                          Price per night from

                          $413

                          Price per night from

                          $413

                          Distance approx 9.42 km from Readsboro

                          (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

                            $120

                            Responds fast!
                            avg. 1 hour 18 minutes

                            Price per night from

                            $120

                            Distance approx 7.74 km from Readsboro Show on Map

                              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

                              $366

                              Price per night from

                              $366

                              Distance approx 8.83 km from Readsboro

                                10

                                #585: 12 Lilla Lane 585-02

                                Vermont / Wilmington

                                Wilmington house

                                3 12 2 nights min

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

                                Price per night from

                                $241

                                Price per night from

                                $241

                                Distance approx 7.7 km from Readsboro Show on Map

                                  10

                                  #B40: 99 North Road B040-03

                                  Vermont / Wilmington

                                  Wilmington villa

                                  3 7 2 nights min

                                  • 3 bedrooms
                                  • sleeps 7
                                  • 2 nights min
                                  • Ask about children
                                  • Pet Friendly

                                  Price per night from

                                  $413

                                  Price per night from

                                  $413

                                  Distance approx 13.07 km from Readsboro

                                    10

                                    Mount Snow 6BR+ Indoor Hot Tub, Sauna, Pool Table, FANTASY Ski Home

                                    Vermont / Dover

                                    Dover house

                                    6 18 3 nights min

                                    • 6 bedrooms
                                    • sleeps 18
                                    • 3 nights min
                                    • Child Friendly
                                    • Private garden

                                    Price per night from

                                    $914

                                    Price per night from

                                    $914

                                    Distance approx 10.37 km from Readsboro

                                    (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 14.56 km from Readsboro

                                        20

                                        Karin's Place

                                        Green Mountains / Bennington

                                        Bennington house

                                        7 30 2 nights min

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

                                        Price per night from

                                        $1,542

                                        Price per night from

                                        $1,542

                                        Distance approx 7.7 km from Readsboro Show on Map

                                          10

                                          #274: 28 Old Witness Tree Lane 274-01

                                          Vermont / Wilmington

                                          Wilmington villa

                                          3 6 2 nights min

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

                                          Price per night from

                                          $275

                                          Price per night from

                                          $275

                                          Distance approx 9.17 km from Readsboro

                                            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

                                            $684

                                            Price per night from

                                            $684

                                            Distance approx 9.01 km from Readsboro

                                              10

                                              #A59: 88 Howes Loop A059-02

                                              Vermont / Wilmington

                                              Wilmington villa

                                              3 8 2 nights min

                                              • 3 bedrooms
                                              • sleeps 8
                                              • 2 nights min
                                              • Ask about children
                                              • Pet Friendly

                                              Price per night from

                                              $241

                                              Price per night from

                                              $241

                                              Distance approx 10.63 km from Readsboro

                                              (5) Excellent 

                                                28

                                                Condo on Haystack/Hermitage Ski Mountain

                                                Vermont / Wilmington

                                                Wilmington condo

                                                3 8 2 nights min

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

                                                Price per night from

                                                $342

                                                Price per night from

                                                $342

                                                Distance approx 10.27 km from Readsboro

                                                (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

                                                  $325

                                                  Price per night from

                                                  $325

                                                  Distance approx 7.71 km from Readsboro Show on Map

                                                    9

                                                    #B83: 24 Meadow View Rd B083-04

                                                    Vermont / Wilmington

                                                    Wilmington house

                                                    2 6 2 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 2 nights min
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $172

                                                    Price per night from

                                                    $172

                                                    Distance approx 18.88 km from Readsboro

                                                    (2) Average 

                                                      5

                                                      Adorable Studio apartment in Brattleboro

                                                      Vermont / Brattleboro

                                                      Brattleboro apartment

                                                      2 1 night min

                                                      • sleeps 2
                                                      • 1 night min
                                                      • Ask about children
                                                      • Pet Friendly

                                                      Price per night from

                                                      $155

                                                      Price per night from

                                                      $155

                                                      Distance approx 14.39 km from Readsboro

                                                      (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 21 minutes

                                                        Price per night from

                                                        $172

                                                        Distance approx 12.97 km from Readsboro

                                                        (1) Excellent 

                                                          16

                                                          Balsam Cottage 4BR, Hot Tub, Pool Table, Fireplace - 5 minutes to the slopes

                                                          Vermont / Dover

                                                          Dover house

                                                          4 10 2 nights min

                                                          • 4 bedrooms
                                                          • sleeps 10
                                                          • 2 nights min
                                                          • Ski
                                                          • Child Friendly
                                                          • Pet Friendly

                                                          Price per night from

                                                          $571

                                                          Price per night from

                                                          $571

                                                          Distance approx 13.96 km from Readsboro

                                                            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

                                                            $570

                                                            Responds fast!
                                                            avg. 1 hour 19 minutes

                                                            Price per night from

                                                            $570

                                                            Distance approx 15.01 km from Readsboro

                                                              9

                                                              MT SNOW NEW SKI HOME W/E-WEEK-MONTHLY or SEASON 3 BR 2 Bath 1.1 TO Mtn parking

                                                              Vermont / Dover

                                                              Dover house

                                                              3 7 4 nights min

                                                              • 3 bedrooms
                                                              • sleeps 7
                                                              • 4 nights min
                                                              • Ski
                                                              • Child Friendly

                                                              Price per night from

                                                              $457

                                                              Price per night from

                                                              $457

                                                              Distance approx 16.02 km from Readsboro

                                                                20

                                                                Casual lux near Hermitage Club & Four Columns Inn

                                                                Vermont / South Newfane

                                                                South Newfane villa

                                                                4 8 7 nights min

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • 7 nights min
                                                                • Nearest beach 10 mi
                                                                • Ski
                                                                • Ask about children

                                                                Price per night from

                                                                $1,710

                                                                Price per night from

                                                                $1,710

                                                                Distance approx 11.93 km from Readsboro

                                                                (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

                                                                  $228

                                                                  Price per night from

                                                                  $228

                                                                  Distance approx 10.29 km from Readsboro

                                                                    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. 39 minutes

                                                                    Price per night from

                                                                    $155

                                                                    Distance approx 7.7 km from Readsboro Show on Map

                                                                      10

                                                                      #389: 8 Bear Lair Lane 389-02

                                                                      Vermont / Wilmington

                                                                      Wilmington villa

                                                                      3 7 2 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 7
                                                                      • 2 nights min
                                                                      • Ask about children
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $241

                                                                      Price per night from

                                                                      $241

                                                                      Distance approx 7.7 km from Readsboro Show on Map

                                                                        10

                                                                        #210: 289 Chimney Hill Road 210-02

                                                                        Vermont / Wilmington

                                                                        Wilmington villa

                                                                        3 7 2 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 7
                                                                        • 2 nights min
                                                                        • Ask about children
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $241

                                                                        Price per night from

                                                                        $241

                                                                        Distance approx 7.63 km from Readsboro Show on Map

                                                                          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. 39 minutes

                                                                          Price per night from

                                                                          $189

                                                                          Distance approx 10.1 km from Readsboro

                                                                            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

                                                                            $211

                                                                            Price per night from

                                                                            $211

                                                                            Distance approx 12.15 km from Readsboro

                                                                            (6) Excellent 

                                                                              16

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

                                                                              Vermont / Dover

                                                                              Dover apartment

                                                                              2 8 2 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 8
                                                                              • 2 nights min
                                                                              • Child Friendly
                                                                              “A CONDO TO KEEP COMING BACK TO!” We've rented this condo with friends many times in the past several years, and it's one of our favorites. Steve is very pleasant to deal with, the condo is clean, sleeps many people comfortably, and overlooks the mini

                                                                              Price per night from

                                                                              $399

                                                                              Responds fast!
                                                                              avg. 3 hours 45 minutes

                                                                              Price per night from

                                                                              $399