Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Sleeps 125 BR2 BA


Sitting on a plateau above the Williams River you'll find the 'Smokeshire Hilltop Farmhouse,' a 5-bedroom, 2-bathroom vacation rental home in Chester. This 3,000-square-foot classic farmhouse sits on a working farm and offers travelers an escape, as well as beautiful grounds at any time of the year.


  • Pets Allowed
  • Central Heating
  • Free Parking
  • Wireless Internet (WIFI)
  • Washer
  • Kitchen


Location Details

Grab your skis and spend an unforgettable day at Okemo Mountain. With 120 trails conveniently situated 17 minutes from the property, Okemo has slopes for rookie riders, Olympic hopefuls, and everyone in between!  You are also within a 1-hour drive of 5 other ski areas, Killington, Stratton, Magic Mountain, Bromley and Mount Snow. Mix it up!

Experience small-town New England with a trip to one of the neighboring towns. Located within 8 miles of Ludlow and Chester, this home is just a stone's throw from unique eateries like Homestyle Hostel, MoJo Café or MacLaomainn’s Scottish Pub; or Historical places like Calvin Coolidge’s Estate or Hildene the summer home of Robert Todd Lincoln. In the summer months, visit the local Farmers Markets antique shops, and craft fairs. Of course, there is always the famous Vermont Brewery Passport Challenge.

Take advantage of your wilderness surroundings by exploring the area's many logging roads and trails. Perfect for hiking, snowshoeing, and cross-country skiing, these trails allow visitors to see the wild side of the Green Mountain State.

Some of the trails on the farm meet up with VAST (Vermont Association of Snow Travelers) maintained trails, making them safe places to snowmobile or mountain bike.


25 reviews
  • Awesome stay!!


    Fantastic. Very peaceful. Loved seeing the horses and sheep in the distance. Blueberry picking onsite, hiking trails out the door, kids playing in the shallow river down the hill. Echo lake and going up the chairlift at okemo were awesome. Fire pit was perfect. Attentive and friendly host. Overall we absolutely loved our stay and plan to go back!

    *This review was originally posted on Vrbo

    Ben l.
    Published August 16, 2022
  • Serene, peaceful, lovely


    Donna and Peter could not be better hosts! They have the most bucolic, peace-filled setting with lambs and horses that you can see from your bed in the morning! The house is clean, comfortable, cozy, there is a very well-equipped kitchen and a fantastic patio, and firepit in the backyard. Right down the road is the Williams River, it was shallow enough for the 3year old to play in all morning. Hiking all around, farm markets, festivals, delicious berries, and the peace and quiet that calm your heart.

    Our family loves it here, we are always sad to go, no matter how much time we've spent on this beautiful farm.

    Thanks to Donna and Peter for sharing this very special place.

    Published June 29, 2021
  • Wonderful house in a great location


    We had a great time at your beautiful farm house. It was the perfect distance to Okemo for some early season skiing. Having the large grounds with sheep and horses right outside made for an enjoyable day staying in. Thank you for hosting us!

    Published May 11, 2021
  • Best winter of our lives


    Our family spent the winter at the Farmhouse this year. It was magical from start to finish. Snow, sledding, skating, bonfires, sheep, horses and a lovely dog named Jen. Peter and Donna are marvelous hosts, sharing their space, their knowledge, their warmth and their kindness. Our family of 11 loves this house, loves this farm and feel truly blessed to be able to spend time in this special place.

    If you are lucky enough to stay here, you are lucky enough indeed.

    Published April 1, 2021
  • Highly Recommended


    We had a wonderful stay at Donna's house over the X'mas holidays. The house is cozy, well stocked and perfect for a large family. Donna is a gracious host, available for questions and responsive. We highly recommend this house to anyone looking for a winter getaway.

    Peggy Tseung
    Published January 4, 2021
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Booking Details

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Property ID: 404693
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