Vacation rentals in Roxbury

Architectural House Prickly Mountain

This architectural showpiece is a high-concept concrete manse featuring well-designed details from FAIA Architect David Sellers, such as a curving staircase, exposed concrete structural elements, double height ceilings and open views. PLEASE READ description carefully and ask questions prior to booking. There are 3 beds, 3 baths, open floor plan kitchen, living and dining area and small grassy yard with a view, tucked away in the forest on Prickly Mountain Rd, Warren in the Mad River Valley

Chalet in the Clouds (Sauna in the Sky!)

This Scandinavian-inspired retreat sits high in the Green Mountains, offering stunning views of Sugarbush and Lincoln Gap. Enjoy unforgettable sunsets from the sauna or wrap-around balconies and unwind in the peaceful surroundings. Whether you’re skiing, hiking, or relaxing by the wood-burning stove or outdoor gardens and fire pit, this home is the perfect getaway for nature lovers seeking comfort, tranquility, and adventure, just minutes from world-class outdoor activities and mountain resorts.

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.

Private Resort Luxury in the Heart of Vermont

Bright and spacious apartment that sleeps 4 in the heart of the central Vermont mountains. Property is 80 Acres surrounded by thousands of acres of state forest. Fully furnished with all amenities with heated indoor parking, air conditioning, and access to amazing outdoor opportunities like skiing and biking in all seasons. The property has new high speed fiber optic internet. Come enjoy all the seasons Vermont has to offer in complete comfort and ease. Reduced rates for extended stays.

Farmhouse at Stickney Farms

Enjoy our private waterfalls! Blend old-world charm with stunning scenery at this Roxbury vacation rental! Situated on 350 acres, this 1860's 4-bedroom, 2.5-bath home is great for family gatherings. With a full kitchen, an office, a deck, fire pit, rolling-hill views, and much more. Bring your pups along and explore the property’s trails or swim/fish in the brook or Third Branch of the White River, both run through the property. Plus, see how syrup is made at the working sugarbush!

Captain Tom's Cabin - Secluded Vermont Getaway

Welcome to Capt. Tom's Cabin. Nestled in the hills of Vermont with a beautiful view of the Green Mts., this 2-storey, 2 bedroom log house on 44 acres offers seclusion, serenity and privacy. Two large bathrooms, full kitchen, central heat, gas fireplace, pond and deck. Great for winter sports enthusiasts and nature lovers. Good wifi, dog-friendly with a fee. Please google and read Vermont's covid restrictions and agree to adhere to them before making a reservation.

Rural house with Horse Boarding & Riding nearby!

Travel with your horse(s)! Rural house in a very quiet neighborhood on a dirt road. You can board your horse(s) next door either in stalls or field and use the indoor riding ring. You can get lessons for you or your children. You will have the main floor and upstairs (approximately 1500 square foot) to yourself with views of forest and mountains. Fiber WiFi internet for your remote work or entertainment. Check our 5* reviews! Discounts applied for longer stays.

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*

Cozy cabin retreat

Escape to a cozy, romantic cottage tucked beside a gently flowing stream—where you’ll fall asleep to the sound of water just outside your window and wake to quiet Vermont mornings. Set in a secluded valley in central Vermont, the cottage offers a peaceful, nature-immersed stay with access to open land, trails, and dark, star-filled skies. Whether you're here to unplug, explore, or simply slow down, this is a place that invites you to settle in.

Cozy Cabin Minutes From Sugarbush

Welcome to Laughing Pines. This cozy cabin is conveniently located in Northfield, Vt 28 minutes from Sugarbush, The Mad River Valley, and 10 minutes from Norwich University. Enjoy the mountain views in a warm and rustic country setting. Come and visit whether you want to play hard or relax. NO PETS (we have allergies in the family) NO SMOKING NO FIREARMS AWD and/or snow tires recommended in the winter and spring months (Oct/Nov - April)

Moonlight Farm Studio · Hot Tub · Vermont Retreat

Welcome to Moonlight Mountain Farm — a peaceful Vermont farmstay. Unplug and recharge surrounded by woods, fields, and mountain air. This private, open-concept studio retreat is designed for couples or small groups seeking quiet, comfort, and a true rural escape — featuring an indoor hot tub, pond and mountain views, and optional outdoor sauna. Whether you’re here to ski, hike, bike, or simply slow down, this is your place to reset.

Off Grid Romantic Cabin near Sugarbush ski resort

The perfect Lovers’ Nest, tucked away on 138 private acres—just you, the forest, and a few curious visitors (hummingbirds, deer, bears). This rustic-yet-cozy 800 sq ft cabin is ideal for romantic getaways, & peaceful recharging—with just enough comfort (including Starlink) to stay connected. Just 25 minutes from Sugarbush, you’ll feel completely secluded—yet still close to the charm, food, and adventure of Vermont’s Mad River Valley.