Holiday houses in Waitsfield

Casa Rio Loco!

This charming guest cottage affords well appointed privacy while being centrally located in convenient proximity to all the activities the Mad River Valley has to offer. Nestled along a quiet oxbow of our namesake waterway, if you have come for the winter sports you will be a 5/7 minute drive to the Sugarbush base areas, and 10 minutes will bring you to Mad River Glen ("ski it if you can"). Explore the towns of Waitsfield and Warren Village in less than 5... Snowshoeing? Walk out the front door!

The Birch Perch! Treehouse with spa and fire pit!

Romantic Honeymoon or fun family fantasy come true this treehouse has it all! Built by The DYI Network Treehouse Guys! Every detail custom crafted in this home in the tree tops makes your ultimate Vermont experience. All just 8 minutes to the lifts at Sugarbush. Kitchenette, cast iron stove, clawfoot tub, washer/dryer, AC, & outdoor shower all encased in a whimsical perch near skiing, waterfalls, biking and hiking. Incredible hillside views from your private deck! Romantic Hot tub in the trees!

Charming and Centrally Located Waitsfield Home.

Ten acres with lovely views in the heart of the Mad River Valley. Post and Beam - open floor plan. Conveniently located, through the covered bridge, less then 2 miles from shops and restaurants in the center of Waitsfield village. Easy access to Mad River Glen, Sugarbush, numerous nordic centers, golf courses, mountain biking trails, hiking and the Mad River for swimming and fishing. Close to numerous wedding venues including our neighbors the Round Barn Inn. Owners quarters are attached.

Green Mountain Retreat close to skiing

This inviting home offers generous space, timeless charm, and all the essentials for a comfortable short- or long-term stay. Spacious 4-bedroom, 2-bath home in the heart of Waitsfield, VT—perfect for families or groups. Enjoy a comfortable living space, fully equipped kitchen, and room to unwind after a day of adventure. Minutes to Sugarbush and Mad River Glen, plus easy access to hiking, biking, swimming holes, and downtown Waitsfield’s shops and dining. Ideal for year-round Vermont getaways.

4BR Mad River Valley Chalet w/ View, Close to All

Welcome to Stars Hollow Chalet, perfect for a romantic getaway, family and friend getaways, or remote work with super-fast internet (rare in the area!). We're on the Fayston/Waitsfield line fantastically close to downtown shops, food, swimming & skiing. *Featured in Food + Wine Magazine!* Explore all the Mad River Valley has to offer right down the street, then retreat back to the chalet, switch into your slippers and cozy up on our comfy green velvet and leather couches by the fireplace.

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

Off Grid Secluded Farm Stay Cabin

In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

Warm Luxury Mid-Century Modern Chalet

Woodward Haus is a stylish MCM retreat with wood, glass, & stone design. Perfect for remote work, a romantic weekend, a multifamily gathering, a girls' weekend, or retreat. MRV offers all season fun: farmer's market, swimholes, farms, hiking, road & mtn bike, golf, climbing, tubes on the river and lake, can't be beat. The house is nestled in the woods w/ beautiful views mountains. The area's food & breweries, including Lawsons are phenomenal. 1 min to MRG & 14 min to Sugarbush. Exp Wifi

Historic District Overlooking the Mad River Studio

This beautiful apartment is located the second floor of Bridge Street's most popular building, neighboring the Covered Bridge with views of the Mad River. The setting is gorgeous, the apartment is immaculate and charming. 15 minutes from Sugarbush and Mad River Glen Ski Resorts, endless hiking trails, Mt. biking, kayaking, golfing, swimming, fishing and walking distance to Lawson's Finest Liquids Brewing Company. Please check out our reviews as they have been nothing but positive!

Sky Zen - Ridgeline Retreat

A modern mountain retreat on 30 private acres – stunning Green Mountain views. ⛰️ 🌅 Saltwater Hot Tub ☕ Espresso Machine & BBQ Grill 🛁 🚿 Spa Style Baths w/Soaking Tub 🔥 Wood Fireplace & Private Washer/Dryer This peaceful, design-forward home features floor-to-ceiling windows, original art, a gourmet kitchen, saltwater hot tub, and a screened yoga hut. Relax in style, soak in sunsets, and enjoy total privacy—just a short drive from skiing, hiking, and I-89.

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

von Trapp Farmstead Little House

Come stay in the beautiful Mad River Valley! Our guest house named the Little House is surrounded by forest and 3.5 miles from the town of Waitsfield. Located on the North East corner of our farmland you'll find yourself less than a mile from our Farm Store where you can stock up on our organic cheeses, yogurts, and meats or beer, wine, and other provisions from over 40 local producers. Enjoy a quiet vacation or a skiing, hiking, biking, or rafting adventure!