Holiday rentals with a patio in Addison County

Charming Barn Guesthouse Near Middlebury College

Come stay at our lovely renovated barn guesthouse in the Green Mountains of Vermont near Middlebury College. Perfect spot for a quiet retreat or home base for your outdoor adventure! 3 min. to Rikert Nordic Center, 9 min. to Middlebury SnowBowl. 40 min. to Sugarbush. 1 hr to Killington. Sleeps 1-6 people on 3 floors: entry level living area and laundry; mid-level with kitchen, bedroom, and bathroom ; upstairs loft bedroom suite with seating area (futon, chairs, bookcase, and TV), and desk.

Cedar Shingle Home on Scenic Road w Hot Tub

Nestled on a tranquil, tree-lined acre, this charming cedar shingle retreat blends modern comfort with timeless character. Cozy up by the fire pit or unwind in the hot tub beneath the stars. The fully-equipped chef’s kitchen is perfect for savoring Vermont’s bounty, while the new screened porch & deck offer ideal spaces for dining or lounging. With a fire pit, two grills, & peaceful surroundings, this serene getaway feels like a private oasis, yet is conveniently close to everything you need.

Lake Dunmore Getaway — Foliage Views & Ski Retreat

About this space Perched directly on the shores of Lake Dunmore, our lakefront getaway transforms into a four-season escape when the temperatures drop. In autumn, enjoy foliage views over the water, crisp mornings on the deck, and easy drives to Vermont’s most scenic byways. When winter arrives, we’re your basecamp for adventure — just 30 minutes to Middlebury Snow Bowl, 45 minutes to Killington or Sugarbush, and minutes to local snowmobile trails, ice fishing spots, and Middlebury College.

Off Grid Secluded Cabin on 37 Acre Farm

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.

Moonlight Woods - Gardener's Log Cabin

Escape to a cozy log cabin on 10 wooded acres. With a covered front porch, seasonal outdoor bath tub, large fire pit, fully stocked kitchen, hotel amenities, high speed Wi-Fi internet and Smart TV. Secluded yet nearby to ski areas, hiking, swimming holes, restaurants, breweries, apple picking and more. Just .5 miles off of RT 100, 22 min to Sugarbush, 20 min to Mad River Glen, and 39 min to Stowe Mtn Resort. 13 min to Waitsfield or Waterbury, 23 min to Montpelier, and 43 min to Burlington.

Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage is located in the heart of Middlebury on a peaceful side street. Completely renovated, AC & heat everywhere, lots of comfy beds, great deck with grill and fire ring, fast WiFi, king bedroom for the parents, fun guest room with 1 queen, 1 full & 1 twin, full bath & 1/2 bath. Walk to restaurants, shops, grocery stores, and even the College! Incredibly well designed home can comfortably accommodate a couple or a crowd! Brand new 55" Smart TV, new beds, linens, sofas, etc.

Vermont Alpine Cabin

Nestled among the ferns and trees, this one bedroom, with office, 1950s cabin is the “Romantic Cozy Cabin” you have been searching for. With a peek-a-boo view of the mountains this property provides calm and tranquility in your very own private retreat. Start your mornings off by watching the sunrise from the front porch with your morning beverage among Vermont’s stunning nature. Retire in front of the gas “wood burning” stove reading, doing a puzzle, or watching a good movie.

Mountain View Retreat

This clean, quiet, ground-level apartment enjoys an out-of-town feel and expansive mountain views while being conveniently located to the town of Middlebury, Middlebury College, the Green Mountain National Forest, the Middlebury College Snow Bowl and the Rikert Nordic Center, and more. This 1 bedroom/1 bath apartment features an open living concept and a fully equipped kitchen and is just 1.5 miles from restaurants and grocery stores and 2 miles from the college.

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*