Vacation rentals in Roxbury

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Top-rated vacation rentals in Roxbury

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Treehouse in Moretown
4.98 out of 5 average rating, 112 reviews

4-Season Treehouse @ Bliss Ridge; Best Views in VT

thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Equipped w. a fabulous yotel fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original Dr. Seuss treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works!

Top guest favorite
An aerial view showcases the vibrant fall foliage surrounding the farmhouse and grounds. A swimming pond reflects the colorful trees, while green pastures and woods create a serene landscape. The picturesque property is set against a backdrop of rolling hills adorned with autumn colors.
Farm stay in Roxbury
4.96 out of 5 average rating, 217 reviews

Moonlight Mountain Farm Vermont Studio w Hot Tub

Welcome, this is a Farmhouse. Our idyllic Farmstay offers a private, spacious, modern studio within a beautiful 1840's farmhouse in rural Roxbury, Vermont. Including a dedicated, private sunroom atrium indoor Hot Tub. Roam our ambling 20 acre property offering a swimming pond, woodland paths, open pastures, and small farm. Explore the headwaters of the Dog River. Revel in Vermont's finest skiing, hiking, biking, beer, and food just up and down the road. Outdoor sauna available for added fee.

Guest favorite
A wooden cabin is set against a backdrop of colorful autumn foliage. The exterior features multiple large windows and a spacious deck with seating arrangements, including two lounge chairs. A grill and stacked firewood are visible on the deck, inviting outdoor gatherings.
Cabin in Roxbury
4.97 out of 5 average rating, 265 reviews

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.

Top guest favorite
A spacious green field stretches towards a tree line, dotted with colorful wildflowers. A modern home is nestled among the trees, with large windows reflecting the bright blue sky and scattered clouds above.
Apartment in Roxbury
4.99 out of 5 average rating, 153 reviews

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.

Guest favorite
A bright studio apartment includes a comfortable black sofa and a small dining area with two stools. Natural light fills the space through a large window, which is adorned with light curtains. Warm wooden walls complement the smooth, light-colored flooring.
Apartment in Braintree
4.96 out of 5 average rating, 135 reviews

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!

Top guest favorite
A two-story log house is set among trees with snow covering the ground. A wide wooden deck features multiple chairs, and a door is visible on the base level. The structure showcases earthy tones and has a circular window above the entrance, enhancing its rustic appearance.
Home in Roxbury
4.92 out of 5 average rating, 221 reviews

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.

Guest favorite
A tiny house stands surrounded by greenery under a clear blue sky. A bright green door contrasts with the wooden exterior, while colorful prayer flags add a cheerful touch. A front porch features a rocking chair and a small table with chairs, inviting outdoor relaxation.
Tiny home in Randolph
4.87 out of 5 average rating, 224 reviews

Tiny House on Vermont 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 three listings at our place. We can accommodate groups of six by booking: Lower Yurt Stay and Upper Yurt on VT Homestead

Top guest favorite
A cozy living area is highlighted by warm wood paneling and large windows allowing natural light. A stylish record player is placed on a small table near a comfortable seating arrangement featuring a light sofa and wicker chairs. A decorative rug and a small stove add to the inviting ambiance.
Cabin in Roxbury
4.98 out of 5 average rating, 186 reviews

Cozy cabin retreat

This is the cozy, romantic cottage you've been dreaming of! Fall asleep to the sound of the stream outside the window. Enjoy sledding, snowshoeing, or XC skiing around the meadow, or use this as a convenient base for all your Vermont adventures. Nestled in a hidden valley in the center of Vermont, the cottage is conveniently located a short drive from many ski areas, award-winning Montpelier and Randolph restaurants, the bustle of the Mad River Valley and I-89.

Top guest favorite
A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.
Tiny home in Warren
4.99 out of 5 average rating, 271 reviews

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*

Top guest favorite
The exterior of the Little House is showcased, featuring a wooden facade and a gray door. The structure is framed by vibrant autumn foliage, with leaves in shades of yellow, orange, and red. A wooden deck leads up to the entrance, surrounded by a serene forest atmosphere.
Cottage in Waitsfield
4.97 out of 5 average rating, 151 reviews

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!

Guest favorite
The exterior of a historic farmhouse features a blend of brick and white siding. The structure is surrounded by green grass and mature trees. A private entrance is visible, along with a seating area with chairs. The roof showcases a modern metal design, enhancing the traditional architecture.
Apartment in Randolph
4.98 out of 5 average rating, 223 reviews

Historic Wayside Farm - a working dairy farm

Located on a historic Vermont farm. The apartment is located on the first and second floor of our large home. This is an ideal place if you want to explore everything Vermont has to offer. We are centrally located, just a short drive away from area ski resorts, hiking trails, mountain bike networks, breweries and more. We are a certified organic dairy farm. The cows can be found grazing the surrounding hillsides.

Top guest favorite
A charming two-story white building features a black metal roof and multiple windows with shutters. A covered porch extends across the front, decorated with vibrant flower baskets. Surrounding greenery contributes to the rural setting, with the presence of a neighboring structure visible in the background.
Apartment in Hancock
4.95 out of 5 average rating, 169 reviews

Suite in the Green Mountains

We have a first-floor,two-room suite with its own entrance in our home, located on an official Vermont Scenic Highway, in the middle of the Green Mountains. The suite has a large sitting room with a kitchenette; a bedroom with queen bed and A/C; and bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".

Popular amenities for Roxbury vacation rentals

When is the best time to visit Roxbury?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ701ﺩ.ﺇ690ﺩ.ﺇ643ﺩ.ﺇ613ﺩ.ﺇ643ﺩ.ﺇ602ﺩ.ﺇ628ﺩ.ﺇ665ﺩ.ﺇ599ﺩ.ﺇ661ﺩ.ﺇ606ﺩ.ﺇ650
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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Roxbury?

    Yes! Work meets play with ease at over 30 vacation rentals in Roxbury featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Roxbury have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Roxbury. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Roxbury?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with free parking, over 20 homes with wifi, over 10 homes with air conditioning, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Roxbury?

    Roxbury has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Roxbury have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Roxbury. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Roxbury have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Roxbury. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Roxbury?

    Experience the best of Roxbury with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Roxbury have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Roxbury. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Roxbury

  • Total vacation rentals

    Explore 50 vacation rentals in Roxbury

  • Nightly prices starting at

    Roxbury vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

  • Verified guest reviews

    Over 3,160 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Roxbury vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Roxbury rentals

  • 4.9 Average rating

    Roxbury stays are highly rated by guests—averaging 4.9 out of 5!

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