Beautiful vacation homes in historic Woodstock VT

Step into your Vermont vacation home for a weekend, a week or a month.  Gray Barns Properties welcomes you home to our very special vacation rental properties. Each home is thoughtfully designed and furnished to make your time in Woodstock comfortable, relaxing and fun!

From the redwood hot tub at Dana Road House and the brook-side deck at Falcon House, to the expansive luxury and indoor pool at The Aerie, you’ll enjoy calling our properties home.

All our properties are ideally sited, just minutes to the heart of Woodstock village. Gray Barns offers vacation homes perfectly suited to host large groups and events, a gathering of family and friends or a romantic Vermont getaway.

Our vacation homes are locally owner managed and meticulously maintained to the highest standards. Expect luxury linens, a fully equipped chef’s kitchen and gracious living spaces throughout each of our properties.

Welcome home. Unwind. Create memories to last a lifetime.

Our Houses Feature

You can expect all of our houses to have these amenities.

  • Fully equipped chef’s kitchen
  • High quality bedding & linens
  • Gracious indoor & outdoor dining
  • Spotlessly clean, beautifully furnished
  • High speed internet. WiFi, cable/satellite TV

What Our Guests Say

The house had very nice linens and everything needed to make us feel right at home. The owner kept in touch with us to make sure we had everything we needed. It was very nice and peaceful. We loved going to the Quechee Gorge and to Woodstock. I would highly recommend this property to others. – Lisa L.T.

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Gray Barns Properties
Average rating:  
 2 reviews
by Kat Gray on Gray Barns Properties
Biased owner review

An entirely biased owner generated review here. Just want to say how grateful we are to our wonderful guests. It's a lot of hard work to open our homes as vacation rentals, but it's all worth it and +++ when our guests experience a special vacation in our beautiful town. We look forward to welcoming you 'home' to Vermont !

by Whitney on Gray Barns Properties
January 2019 at Falcon House

Kat was great, responded to all messages very quickly and was very helpful answering our questions. My husband and I came up to Vermont with another couple to go skiing at Killington mountain. The house was perfect and Woodstock is a lovely little town. Everything surpassed our expectations, it felt like we were staying at someone’s home - not a rental home. We found things to be laid out very thoughtfully, everything was convenient and extremely cozy. The sauna was a huge plus after skiing all day, really helpful. And everything was so clean. Would definitely stay again would recommend.