Family-friendly holiday rentals in Orange County

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Fairytale cabin at The Wild Farm

Lay in bed and look out the huge picture window at the farm. You might see cats climbing trees, hummingbirds, snowflakes falling, lightning storms and many more beautiful moments. We have a Wolf, don't be alarmed she is as friendly as can be and will greet you and escort you to the cabin. If you like nature, animals, walking in the forest, cuddling up by the wood stove, then this is the place for you. The cabin is surrounded by gorgeous perennial gardens. We look forward to hosting you!

Off Grid Tiny House

This sweet little house is great for those who want to get away from it all. It's like camping but with many more creature comforts. Hot and cold running water and a fantastic hot outdoor shower! The house does not come with sheets and towels but if you need that, please let me know and I’ll make that happen for a small fee ($15)! Great for kids! Plenty of mountain biking and hiking from your front door. Lots to explore. Nature right outside your door! 10% veteran discount.

Tiny House on Vermont Homestead

We are located in the hills of central VT, close to good hiking, skiing and swimming. Disconnect to reconnect. Our homestead is based on permaculture landscape design.Relax by the living pool, or kick back in an Adirondack chair looking out at the hills of VT. We have an ideal environment for digital detox. This is one of three listings at our place. We can accommodate groups of six by booking: Lower Yurt Stay and Upper Yurt on VT Homestead

Private Barn On a Hilltop in Fairlee, Vermont

This carefully renovated barn is located in the hills of Fairlee, five minutes from I-91. A stand-alone private space with two spacious living areas and decks overlooking ponds and the mountains. You're welcome to bring your dog; please note there is a $75 pet fee for the length of your stay. With direct access to extensive hiking trails and minutes from Lake Morey and the Lake Morey Country Club there's lots of fun things to do.

Windswept Acres Sugarhouse

Looking for a Rustic adventure? ...the Sugar House is your stop. Well water no longer comes via a hand pump (we just added running hot and cold water!) but there is still an outhouse in the back. A favorite of many of our "regulars" with a great view of the sunrise. You are on 55 acres with two ponds for swimming, fishing, and paddling, plenty of hilltops to hike to and soak in panoramic views... and plenty of privacy.

A Simple Cabin at Four Springs Farm

Privately located walk-in camping sites are part of this beautiful working organic farm on a west-facing Vermont hillside. Guests will be dazzled by star-studded skies, treated to spectacular sunsets, and entertained by the two young farm cats. The farm is mosquito free but has millions of fireflies in summer. Have fun exploring. It's nature's playground at her best!!!

Luna Cabin - Private brookside cabin on homestead

Step away from it all into the quiet mountains of old Vermont where you'll find our tiny cabin nestled on the banks of our brook. Sway in the hammock by the private fire pit or head inside to curl up on the couch and revel in a sublime, uninterrupted view of the forest. This space beckons you back to simplicity, where you can breath deeply and let your soul smile.

Private Tiny House Retreat

The Hemlock Tiny House provides a cozy place to stay in wooded Vermont. You have the Tiny House to yourself, along with a private patio. Must be able to climb ladder to access lofted bed. No kitchen. Well-behaved animals allowed 1 Queen-sized lofted bed 1 Fold-down sofa bed (good for someone who can sleep anywhere or child)