
Holiday rentals in Roxbury
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Top-rated holiday rentals in Roxbury
Guests agree: these stays are highly rated for location, cleanliness and more.

Lower Yurt Stay on VT Homestead
We are located in the hills of central VT, close to hiking, skiing and swimming. Disconnect to reconnect! Our homestead is based on permaculture landscape design. Unwind in the traditional Finnish Sauna, relax by the living pool, 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 on VT homestead and Tiny house on VT homestead

Earthen Yurt in Green Mtn Wonderland
Secluded mountain wonderland near Vermont's best hiking, mountain biking, and swimming holes! Enjoy a 25-acre homestead all to yourself, w/two beautifully-appointed yurts & a cabin. One-of-a-kind sculpted earth design, persian rugs, organic linens, & full kitchen w/many artisan touches. Stargaze around the fire circle under a glittering dark sky. A paradise for outdoor adventurers & nature lovers; a haven for digital nomads, writers, & creatives; a refuge of lush natural beauty & deep quiet.

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!

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.

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.

Howling Wolf Farm Yurt--A Magical Glamping Retreat
Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

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!

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.

Weasley's Enchanted Treehouse @ Vermont ReTREEt
Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling perfect for any admirer of a beloved wizarding world, or anyone who just truly appreciates a 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 among the branches of several maple trees, providing a magical and secluded escape from the hustle and bustle of everyday life.

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.

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*
Popular amenities for Roxbury holiday rentals
Other great holiday rentals in Roxbury

The Vines

Quiet, Cozy Loft w/ Mountain View’s! Remote Work!

Cozy 1 bedroom guest suite in Lincoln VT

Off Grid Romantic Cabin near Sugarbush ski resort

Sky Zen - Ridgeline Retreat

Charming and Centrally Located Waitsfield Home.

Maple View

Peaceful Log Cabin in the Woods
When is the best time to visit Roxbury?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $249 SGD | $245 SGD | $228 SGD | $217 SGD | $228 SGD | $213 SGD | $215 SGD | $221 SGD | $228 SGD | $234 SGD | $215 SGD | $230 SGD |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°C | -2°C |
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.
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.
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.
Are there pet-friendly vacation rentals in Roxbury?
Four-legged friends are welcome in Roxbury. Choose from more than 20 vacation rentals for guests traveling with pets.
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.
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.
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.
Quick stats about holiday rentals in Roxbury

Total holiday rentals
Explore 50 holiday rentals in Roxbury

Nightly prices starting at
Roxbury holiday rentals start at $117 SGD per night before taxes and fees

Verified guest reviews
Over 3,160 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Roxbury holiday rentals include wifi 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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- Okemo Mountain Resort
- Sugarbush Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Lucky Bugger Vineyard & Winery
- Whaleback Mountain
- Autumn Mountain Winery
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Montshire Museum of Science
- Ethan Allen Homestead Museum
- Mt. Eustis Ski Hill
- Burlington Country Club
- Cozy Cottages & Otter Valley Winery
- Country Club of Vermont
- Leahy Center for Lake Champlain
- Storrs Hill Ski Area
- Killington Adventure Center
- Vermont National Country Club
- Lincoln Peak Vineyard
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