Vacation rentals in Roxbury

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

The Barnbrook House

Come relax in the serenity of the quiet countryside. This home boasts beautiful views, a large stone fireplace, and stained glass windows throughout the home. Enjoy the comforts of home with a full kitchen, amenities, and beds with 1500 thread count sheets while exploring the interesting features of this one of a kind house. Sit by the spring fed pond overlooking the property laced with apple trees. The home has direct access to short walking trails and is close to VAST trails for snowmobiling.

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 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.

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.

Upper Yurt Stay on VT Homestead

We are located in the hills of central VT, close to good hiking, skiing and swimming. Disconnect to reconnect! Our homestead is based on permaculture landscape design. Relax by the living pool, unwind in the traditional sauna, or kick back in an Adirondack chair looking out at the hills of VT. We have an ideal environment for digital detox. This is one of two listings at our place. We can accommodate groups of six by booking: Lower Yurt Stay on VT and Tiny house on VT homestead

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!

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.

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!

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.

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.