Family-friendly holiday rentals in Orange County

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

Family · Kitchen · Amenities

Lower Yurt Stay on VT Homestead

We are located in the hills of central VT, close to hiking, skiing and swimming. Disconnect to reconnect! Our homestead is based on permaculture landscape design. Unwind in the traditional Finnish Sauna, 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 on VT homestead and Tiny house on VT homestead

Indoor spaces · Kitchen · Value

The Vershire Fortress

Breathtaking views, mountain fresh air, and tranquility in the hill town of Vershire, VT; the Fortress looks out over the White Mountains to the East during the day and the Milky Way above at night. The property spans 6 acres that are available to all guests looking for a bit of snow-shoeing or a walk in the woods. Plus recent renovations! Designed and built by architect, Nick Fabrikant, it offers splendid open floor plans and incredible natural lighting through the many South-facing windows.

Family · Indoor spaces · Hospitality

The Guest House at Chandlery Farm

This classic Vermont farm estate has everything that description implies: end-of-the-road privacy with breathtaking views, where the only sound is the wind rustling through the leaves. The manicured gardens, stone walls and quaint but luxurious home seem plucked from classic American folklore. Guests can drink their morning coffee while soaking in views of rolling pastures and forested hills, and spend their days exploring the property's trails, and the beautiful towns and countryside nearby.

Indoor spaces · Kitchen · Getting around

Garden Retreat, Lake Fairlee, Dartmouth & Ski-way

Set in a lovely 3 acre garden setting, our Airbnb is 1/4 mile from the lake and 23 minutes from Dartmouth College or the Ski-way. This private, comfortable apartment is built onto our house with its own entrance, hardwood floors, radiant heat, large windows, full kitchen and bath, & gorgeous garden views. The wrap around loft has 3 generous semi-private sleeping areas with 2 queens + 1 twin. A queen futon is downstairs. Rental includes pass to Treasure Island Recreation area & beach: 1.5 mi..

Indoor spaces · Kitchen · Skiing

Cozy Bow House Perched in Trees w/ Hot Tub & View

The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Family · Kitchen · Layout

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.

Kitchen · Indoor spaces · Nearby

Off Grid Tiny House

This sweet little house is great for those who want to get away from it all but still have high speed WIFI. Like camping but with more creature comforts. The house has hot and cold water in the summer. We turn it off at the end of October. The house does not come with sheets and towels but we offer them for $15. Great for kids! Mountain biking and hiking locally and right out your door. Excellent swimming pond! 10% veteran discount. Spectacular and cozy in the winter. Lots to explore!

Kitchen · Indoor spaces · Check-in

Historic Wayside Farm - a working dairy farm

Located on a historic certified organic dairy farm, this lovely apartment offers guests a cozy retreat with one comfortable bedroom and a clean, well-kept bathroom. Whether you’re relaxing after a day of exploring or enjoying a quiet morning coffee, this marvelous spot provides a peaceful atmosphere. We are centrally located, just a short drive away from area ski resorts, hiking trails, mountain bike networks, breweries and more. We hope you'll enjoy your stay at our apartment.

Indoor spaces · Family · Cleanliness

Scandinavian design Chalet hiking trail + hot tub

This bright, well-designed Scandinavian-style chalet is the perfect cozy retreat. Nestled in the woods on a plot of 20+ acres, it offers scenic views and a private hiking trail leading to beautiful vistas, transforming into a winter wonderland for skiing adventures, a summer paradise for outdoor relaxation, and a vibrant canvas for leaf peeping during Vermont's stunning fall foliage season. Goodland wood burning hot tub is available 365 days a year.

Indoor spaces · Kitchen · Solo travel

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 a large pond for swimming, fishing, and paddling, plenty of hilltops to hike to and soak in panoramic views... and plenty of privacy.

Kitchen · Family · Amenities

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!!!

Family · Kitchen · Shared spaces