Family-friendly vacation rentals in Appalachian Mountains

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Moonlit Chalet

Not just a room with a view....but a whole home with VIEWS and lots of property for privacy and the experience of "A Picture Perfect Mountain Chalet" Relax and Enjoy Long-Range Mountain Views from the Living Room and Decks of this Stunning 2 Bed / 2 Bath Home. Modern Kitchen Opens to Stone Faced Fireplace & expansive Windows, lots of outdoor space to enjoy with nature, Recently Remodeled for the modern yet rustic appeal, on 25+ acres with hiking trails onsite- near Waynesville and Asheville.

Best views in Highland County !

Located in the pristine Mill Gap Valley. At night you can reach out and touch the stars. National Forrest is close by too. Enjoy the peace and tranquility that can only be offered in Highland county. The farm along with our Maple Syrup is certified Organic. From our apple trees to our hay and pastures. We are Organic! If you would like a tour of our farm or maple operation, let us know! By September 2020, there will be a new outdoor living area with a hot tub and dining.

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

Stone House 1807. Comfort, Peace and Nature.

Historic 200 yr old stone cottage, on three floors, renovated to a high standard, creating a very comfortable and peaceful retreat, whilst retaining soul and character. Extreme cleanliness is a priority. Quality bedding assures a good nights sleep. The bathroom offers a rain shower and soaking tub. The kitchen is fully equipped and fresh produce is available from the neighboring organic farm in season. Good hiking trails are accessible from the house.

Treehouse on Walker Pond, Private Hot Tub, Canoes

The treehouse is at the very edge of Walker Pond. You and your guest are welcome to enjoy our 40 acres of forest/wetland, go canoeing in our canoe, soak in the custom made cedar hot tub, hang out at the fire pit/garden area, or just enjoy having a private holiday. The treehouse is located just 5 minutes from downtown Newport and is 22 minutes to Jay Peak Ski Resort.

Sunrise Spring Glamp

Yesterday, It was a forgotten dairy farm... Today it's a sanctuary to free your spirit. We're delighted to share this beautiful spot with guests. The glamp is a part of a bigger initiative to build a community, intent on innovating a culture that fosters the human spirit rather than extinguishing it. Find Frontier of Life on fb to learn more.

Architectural wonder in the woods

Unique experience, secluded. Enjoy a weekend or a few days eco-friendly retreat in an architectural, geometric masterpiece on 30 preserved acres just minutes from all that Rhinebeck and the Hudson Valley have to offer. The house is an open plan, and though it has zero bedrooms, it can sleep 4!