
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.

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.

Cute and Functional One Bedroom in Barre VT!
Enjoy a stay at this stylish experience at this centrally-located place! Three separate rooms. Large Bathroom and Kitchen and Bedroom/Living Room. The full size bed has a trundle underneath to pull out a twin size bed. The shades and curtains in the bedroom are blockout shades to keep out the lights of the night. Lots of off street parking and separate private entrance. You will be on the first floor apartment. There is an apt above the studio that is also rented to Air B and B travelers!

Garden Getaway
Second floor, 2 bedroom apt above a garage located in Williamstown VT, four miles from I-89. We live right on sight to address any and all needs. 6 miles from Millstone Trails 8 miles from Barre the Granite capital of the world. 9 miles from Norwich University 13 miles from Braggs Farm Sugar House and Gifts & Morse Farm Maple Sugarworks. 18 miles from Vermont State University Randolph Located less than hour from Killington and 24 miles to Sugarbush, and 34 miles from Bolton.

Alder Brook Cottage: A Tiny House in the Woods
From the moment you cross the cedar footbridge over Alder Brook, you'll know you're somewhere special. Featured in Boston Magazine and CabinPorn, Alder Brook Cottage is an inspired, rustic dream cabin located in the woods of Vermont's Northeast Kingdom. Surrounded by a crystal clear stream and 1400 acres of rugged forest, it is the perfect getaway for glampers looking to experience the tiny house life. Minutes away from Caspian Lake, Hill Farmstead Brewery & Craftsbury Outdoor Center.

Historic Wayside Farm - a working dairy farm
Located on a historic certified organic dairy farm, this lovely apartment offers guests a cozy retreat with one comfortable bedroom and a clean, well-kept bathroom. Whether you’re relaxing after a day of exploring or enjoying a quiet morning coffee, this marvelous spot provides a peaceful atmosphere. We are centrally located, just a short drive away from area ski resorts, hiking trails, mountain bike networks, breweries and more. We hope you'll enjoy your stay at our apartment.

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.

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*

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!

Cabin in the Woods
This cozy cabin is on a well maintained town (dirt) road a short walk to Blueberry Lake (on National Forest land, non-motorized) and is within 15 minutes of Breadloaf Wilderness Area, Sugarbush Ski Resort, Mad River Glen Ski Area, restaurants and dining, arts and crafts, sports and specialty shops. It's wooded, quiet, has a light open feeling inside.
Popular amenities for Roxbury holiday rentals
Other great holiday rentals in Roxbury

Cozy 1 bedroom guest suite in Lincoln VT

Off Grid Romantic Cabin near Sugarbush ski resort

Elegant 1-Bedroom Home in Stunning Location

Cozy VT Getaway - Fully Furnished for Longer Stays

Modern guesthouse in Mad River Valley Fernstone

Charming and Centrally Located Waitsfield Home.

Stunning Modern Retreat Overlooking The Mad River

The Beehive at Bergamot + Amor
When is the best time to visit Roxbury?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $245 SGD | $241 SGD | $225 SGD | $215 SGD | $225 SGD | $211 SGD | $212 SGD | $218 SGD | $225 SGD | $231 SGD | $212 SGD | $227 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.
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 a kitchen, over 20 homes with wifi, over 10 homes with air conditioning, over 20 homes with free parking, 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 holiday rentals in Roxbury

Total holiday rentals
Explore 50 holiday rentals in Roxbury

Nightly prices starting at
Roxbury holiday rentals start at $116 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!
Destinations to explore
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- Okemo Mountain Resort
- Sugarbush Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Dartmouth Skiway
- Whaleback Mountain
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Montshire Museum of Science
- Storrs Hill Ski Area
- Burlington Country Club
- Ethan Allen Homestead Museum
- Mt. Eustis Ski Hill
- ECHO, Leahy Center for Lake Champlain
- Vermont National Country Club
- Killington Adventure Center
- Lincoln Peak Vineyard
- Montcalm Golf Club
- Shelburne Vineyard




