Family-friendly vacation rentals in Chittenden

Mountain Getaway Pet friendly

Escape to our charming getaway, ideally located in Rutland just 20 minutes from the world-famous Killington Ski Resort! Whether you're here for skiing, snowboarding, hiking, or simply enjoying the serene beauty of Vermont, our home offers the perfect base for all your adventures. Our home offers a cozy and welcoming environment, perfect for families, couples, and groups of friends. You'll love the combination of comfort, convenience, and proximity to the best of Killington's outdoor adventures.

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front or 4 wheel drive vehicles with good all season or snow tires required in the winter. Not suitable for toddlers or young children.

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! Winter: MUST have AWD/4x4 for winter access on dirt road and driveway. Snow tires recommend. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the beauty Vermont has to offer!

Charming tiny house with great VT location!

Curious about tiny home living!? This newly constructed 180 sq ft. house will let you experience comfort in charming farmhouse/cottage style. (Shiplap walls anyone?) Only 25 min to Killington, and 12 min from Mtn Top Inn, Downtown Rutland, or Brandon VT makes the location very convenient. Situated on over 2 acres of private back yard, overlooking beautiful Sugar Hollow Brook in the heart of Pittsford, Vermont. Walking distance to village general store, library and the Pittsford trail system.

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

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.

Remote Cozy Yurt with Sunset Views

Enjoy some time in a secluded yurt nestled in a quiet valley with spectacular sunset views. It comfortably sleeps 4, but can accommodate more. There is a bathhouse with an outdoor shower, compost toilet, and sink. Complete with propane stovetop, grill, and all necessary kitchenware. Stays in colder months will enjoy the warmth and comfort of a wood stove. Guests can also enjoy a small trail system on property for exercise or leisure. We hope you will come enjoy this peaceful retreat!

New Firepit, Great Location, Dog Friendly, Kitchen

Welcome to @MendonMtGetaway - my warm & cozy VT retreat! With 3 bedrooms, comfy living room, full kitchen, washer/dryer, AND office space - I hope you'll feel at home right away. You are in a wonderful location here. Turn left & you are just minutes down the road from ski heaven - Killington and Pico Mountains! Turn right, and you're just minutes from cute & historic Rutland. Either way you’ll find tons of great outdoor activities & hiking, and lots of local shops and restaurants.

The Swallows Nest in a wildlife preserve

NEW THIS YEAR: High speed internet, Heat pumps for heat and AC throughout the house, and a new refrigerator/ freezer Secluded and beautiful, at the end of a gravel dead end road, the Swallow’s Nest is part of our organic farm and wildlife refuge. You’ll find serenity here with huge open vistas. We are two miles from the town of Brandon. Brandon has restaurants, shops, art galleries and music venues. Check out what’s happening in Brandon at the Brandon area chamber of commerce.

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

The Guest House at Sky Hollow

This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Convenient Vermont Getaway

Conveniently located near the top ski and mountain bike attractions, incredible trails, resorts, and the towns of Woodstock, Middlebury, Killington, Pico, and Rutland. This historic property has been in existence since 1832 and has been lovingly maintained with a backdrop of the Adirondacks beyond the picturesque pasture. This one bedroom apartment is located downstairs in the two story duplex.