Cabin holiday rentals in Wintergreen Resort

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

Value · Family · Accuracy

Gameroom~Mtn View~Fireplace~Main Level King~Grill!

The Blue Ridge Cabin is at the base of the mountain on the “151 Brewridge Trail”, just mins to wineries, breweries, hiking, skiing, golfing & lake fun. Experience a mountain vaca in this fun bear-themed cabin on 2 private acres, tucked away yet close to it all! Enjoy 12+ wineries & breweries within 15mins, 1/2 mi to Devils Backbone Brewery, 1 mi to Bold Rock Cider, 10 mins to Appalachian Trail, Shenandoah Nat. Park & Wintergreen Ski Resort! Charlottesville/Waynesboro 30mins. A perfect home base!

Value · Family · Hiking

3 Levels · 3 Scenic Decks · Game Room · Hot Tub

Wake up to Blue Ridge views and start the day with coffee on the deck. Rockstar Ridge sleeps 12 across 3 levels, with 5 bedrooms, 3.5 baths, and 2 wood-burning fireplaces for cozy evenings. Soak in the private hot tub, fire up the gas grill, and gather in the music-themed game room with a pool table, foosball, arcade, and a Victrola music player. You'll also find a fully stocked kitchen, a wine and coffee bar, a washer and dryer, and a workspace. Wintergreen Resort is just 6 minutes away.

Family · Value · Kitchen

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Welcome to our luxurious tiny house nestled in the heart of Nelson County, Virginia. This enchanting retreat, surrounded by the majestic Blue Ridge Mountains, offers an unparalleled experience in a landscape dotted with wineries, breweries, distilleries, and sprawling farmland. This luxury tiny house was built in 2022 and is available for couples, solo travelers, or a small family wanting to explore this beautiful stretch of the Blue Ridge Mountains. FREE Electric Vehicle Charger on-site.

Value · Family · View

The Bear Dance Cabin at Wintergreen Resort

Tucked back in the woods in the Wintergreen Resort, we're on the top of Wintergreen Mountain, elevation just under 4k, near all the resort's amenities. Our family built on Wintergreen Mountain after learning how unique and beautiful the seasons are here. The cabin quickly became a new member of the family and we can’t imagine not having her in our lives now. Ten years after building we decided to provide short term rental and the experience has been beyond what we had ever imagined. Enjoy!

Location · Value · Condition

Cedar Base Camp

Enjoy everything in the area to enjoy your holiday in this cozy cabin at the top of Wintergreen. You will have plenty of room with three bedrooms and a loft. Meals can be prepared and enjoyed with the well appointed kitchen and propane grill on the deck. Everyone will love the rustic bathroom with tin tub, or the European style rain shower in the master bathroom. Relax after an exciting day in the private hot tub. Hiking is down the street and the resort is just down the mountain.

Family · Location · Layout

Serene Wintergreen Retreat, Nestled in the Trees

Welcome to our cozy Wintergreen cabin in the trees! You'll truly feel at peace with nature on the three levels of decks and great privacy. The interior has been fully renovated with modern finishes. The light-drenched living room with a wall of windows brings the sense of nature inside. Outside, enjoy the hot tub, covered dining for 10, firepit, and grill/pizza oven area. We are close to skiing and some of the best hiking trails, wineries, and breweries in Virginia. Plus, pet friendly!

Value · Family · View

Stylish 7BR/16 pp Wintergreen Resort Home Ski/Hike

7BR/ 6.5B perfect mountain getaway! Tucked away in the woods & situated on 1/2 acre lot, this peaceful escape is less than 5 min from skiing, hiking, spa, pool, tennis & activity center w/i Wintergreen Resort. This spacious home feat. new ss appl, new furniture, HW flrs, granite cntrs, deck w/new grill, open flr plan, 75” tv, new outdoor furniture, new washer/dryer, darts, games/puzzles & new ping pong table. 6 BRs have en-suite baths & 4 have tvs; very private for large grps.

Location · Family · Accuracy

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

Value · Location · Layout

Modern Cabin with Hot tub and Sauna

Welcome to Blue Ridge Hollow! This designer-decorated cabin in the heart of Wintergreen has one of the best outdoor spaces in the area. Relax in the hot tub or cedar barrel sauna, then enjoy a meal at the oversized outdoor table or sip wine around the firepit. The updated kitchen is fully stocked and open to the living room and sun-drenched dining room. 3 bedrooms are masters, the others share a bathroom, and the downstairs game room can be a 6th bedroom. Plus, pet friendly!

Location · Value · Pets

Lakefront Cabin w Stunning Curated Decor & Hot Tub

✨ A Marvelous Night for a Moondance Awaits ✨ Welcome to Moondance—a lakeside log cabin with serious style and mountain soul. Designer interiors, cozy fireplaces, an après-ski game room, and dreamy views set the stage. Whether you're sipping wine on the deck or roasting s’mores under string lights, this is where memories are made. Minutes to wineries, Wintergreen, and the Blue Ridge Parkway. Relax, reconnect, and maybe do nothing at all. We support that.

Family · Value · Long stay

Relax Among the Trees at the Canopy House

Escape to The Canopy House, a spacious light-filled 4 bedroom retreat at Wintergreen Resort, just 5 minutes from the slopes and walkable to scenic trails. Perfect for families and groups, enjoy 2 king ensuites, a queen bedroom, bunk room, stocked kitchen, fireplace, playroom, and screened porch with fire table. Ski, hike or explore Route 151 wineries and breweries, then relax among the trees. Sleeps 8 with an EV charger available.

Location · Family · Quiet