Family-friendly holiday rentals in Rochester

Bill’s Barn Rochester Vermont 3 Bdrm entire house

Our place is a 1980's barn/woodshop that never housed animals that has been converted into a lovely three bedroom home.We are 20 minutes from Rikert 2019 hosts of the Bill Koch Festival and the Middlebury College Snow Bowl.The place is light and airy with southern and eastern sun.The main living room has 13 foot ceilings with lots of couches, arm chairs and places to hang out, read and or relax.We are in the heart of the Green Mountains with skiing and colleges, an easy drive from the house.

Stock Farm Hideaway


Discover a hidden gem in Vermont! Nestled within 125 acres of farmland, this centrally located guest suite offers tranquility and beauty. Connected to the main home, it ensures your privacy with a private entrance. Wake up to the sweet melodies of birds and sip your favorite coffee while observing wildlife. Embark on walks along the serene property, all while relishing the views. Located on a charming dirt road, it's just a short drive to Randolph's restaurants. Your idyllic escape awaits!

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the National Forest. Home with deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from town. 35 min to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. Snow tires or chains needed from Dec.-March. Please note that we cannot help you if your car gets stuck en route to the house.

Cozy Cabin Studio

Relax in this peaceful quiet space! This studio apartment is above a shared garage/entrance with the home owner. The homeowner and her daughter and 2 over friendly dog live on the property. The cabin is on 5 acres with a beautiful yard and pond that you can enjoy. The studio is 5 minutes from the town; local restaurants, train station, theater are some of the few attractions. The highway is 7 minutes away. 3 miles dirt road The Vermont hills and trails await your adventure!

Cottage in the Heart of the Green Mountains

Welcome to quintessential Vermont! Come stay at my cozy yet spacious, rustic yet modern, much-beloved Red Acre Cottage. Red Acre Cottage is nestled on a scenic ridge in the idyllic town of Rochester, just east of the Green Mountains and right off of Vermont Scenic Byway Route 100, one of the state's prettiest roads. Red Acre Cottage is an easy drive to Killington/Pico, Sugarbush, Mad River Glen, Rikert Nordic Center/Blueberry Hill XC skiing, Suicide Six, and Stowe Mountain.

Hancock hideaway

Skiing, snow biking 10 minutes away at Middlebury Snow Bowl and Rikert crosscountry. Sugarbush and Killington half hour drive. Snowshoeing and hiking right behind house in the Green Mountain National Forest. Easy drive to river swimming holes and lakes. Excellent restaurants in Waitsfield and Middlebury - about half hour. Good restaurant, cafe, small grocery store, in Rochester, 4 miles. Great location, beautiful views, lovely little house, totally private, romantic.

The SugarMaple Treehouse @ Vermont ReTREEt

Nestled amidst the Green Mountain National Forest, this glamping style treehouse is cradled by three maple trees and stands as a haven above the ground. It was hand crafted by us to offer a reTREEt in the heart of central Vermont. We are centrally located between Killington and Sugarbush with plenty of outdoor activities to enjoy. The treehouse now has a bath house with a limited kitchenette just steps away from the treehouse.

Funky, family-friendly cabin

Our funky, fun house is nestled in the woods, with a waterfall and brook rushing by outside the large wall of windows. Situated in the Green Mountains, this is the perfect place to relax and play. The large open-floor plan is perfect for families with school-age children. Families with infants and toddlers may not find our home as friendly, as the waterfall, loft and attached farm buildings may create some safety challenges.

The McKinley House

In the village of Rochester. Walk to bakery, cafe, tavern, grocery, and town green. Hiking, biking and Nordic ski trails! Thirty minutes to SugarBush, Pico, Middlebury, and Killington. Located in the heart of the Green Mountain National Forest. We are dog friendly but we require a conversation about it before you can show up with your dog. We charge $100 pet fee for your stay.