Exceptional vacation rental homes

in historic Woodstock, Vermont

Step into your Vermont vacation home for a weekend, a week or a month.  Gray Barns Properties welcomes you home to our beautiful,  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 resort style living of Windfall at Quechee Lakes. You’ll enjoy calling our properties home.

All our properties are ideally sited, very private yet just minutes to the heart of Woodstock village. Gray Barns offers vacation homes perfectly suited to host 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.

#notetoself while finishing round 2 of snow shoveling❄️
Pretty sure that was me who said “So happy it’s snowing again, we need it!!” 🙋🏼‍♀️
#vermontstrong #802 #winter #winterwonderland #shoveling #lovemynewsnowtires #4runner
Ready to welcome the New Year @windfallvt !
🥂Table is set
🔥Fire is lit
🌟Porch light is on
Come on in and be welcome🍍
DM me if you'd like to stay at this cozy condo, just listed it on @airbnb
#vermont #vermontvacation #vacationrental #welcomehome #vermontbyvermonters #skihouse #quechee #hygge #hyggehome #airbnbsuperhost
A beautiful late autumn day @danaroadhouse 
#vermontfall #autumnvibes #cozy by the fire #airbnb #welcomehome
A beautiful Vermont autumn  day made even more special with @graybarnspottery stunning artisan pottery 
🍂 so grateful for these amazing gifts 😌
#vermontlife #vermontfoliage #artisanpottery #vermontermade #autumnvibes #grateful

Our Houses Feature

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

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

What Our Guests Say

What can I say? This home is the perfect sanctuary for our city dwelling family of 5. The layout and design of the home is absolutely stunning. Kat is highly responsive and a warm host. No detail is forgotten. Great amenities- the towels are soft, the views are relaxing, the kitchen has everything you would need. We would definitely return in a heartbeat. Walking the mile or so to the Woodstock farmers market was a highlight! And we had that fireplace going whenever we were home, although the Nest control for the heating was another easy way to stay nice and toasty. Absolutely beautiful stay. Do yourself a favor and book this place! – Dec 2021

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Average rating:  
 2 reviews
 by Khris
Peaceful Vacation Home

We picked The Aerie because it offered a private indoor pool, no noisy neighbors, gorgeous mountain views, and two master suites. We were surprised and delighted by all the other special touches the owners provided: lots of soft throws for snuggling with books, firewood for the outdoor fire, an assortment of games and puzzles, and pretty much anything else we forgot to pack. The drive to the local ice cream shop was five minutes away, and the town, Woodstock, is as pretty as a New England postcard. My only complaint is that it rained a couple of days, but I don't suppose Kat has a lot of control over that. 🙂

We wish we could create the perfect weather for you too Khris! We thank you for your gracious comments and are delighted you , your family and friends enjoyed your time at the Aerie this spring. Woodstock is truly a special place, it's our pleasure to share this treasure with you!

 by Whitney
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.