
Apartment holiday rentals in Wintergreen Resort
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Top-rated apartment rentals in Wintergreen Resort
Guests agree: these apartments are highly rated for location, cleanliness and more.

Endless Mountain Top Views from All The Way Up!
Our warm and inviting condo combines amazing proximity to hiking with to-die-for views of the Blue Ridge Mountains and the horizon 75 MILES distant! Our condo sits a mere 400-yd walk from the closest hiking trail and also has direct access to the ridge line walking area - perfect place for a morning stroll! This updated and modern mountain themed space features: ✸ Newly renovated! ✸ Stocked modern kitchen! ✸ Two full bathrooms! ✸ Helix Hospitality Mattresses!! ✸ Cozy Fireplace w/ wood provided!

Spacious lower level Airbnb! READ SUMMARY!
Hello everyone! I’m not going to try to convince you to stay at this Airbnb but instead address the issues that guests have complained about in reviews. This listing is priced accurately and cheap because there isn’t much besides 2 king beds, bathroom, washer/dryer. There is a bit of noise from upstairs when people walk around but usually no later than 11 PM. Please keep in mind when reviewing that you’re not paying very much to stay here. If you’re going to complain, please stay elsewhere.

Cozy stay with scenic views on a horse farmette
Cozy apartment with beautiful views on a horse farmette on the most scenic road in the county. Located within 15 miles from Charlottesville and only 6 miles from Shenandoah National Park and the Blue Ridge Parkway, this vacation rental is the perfect spot if you are looking for places to hike, scenic drives or visit the many wineries, breweries or cideries located in close proximity. The apartment is situated over the garage and has its own separate entrance offering guests plenty of privacy.

Wintergreen Getaway
Relax with the whole family at this peaceful place to stay. Enjoy morning coffee and evening cocktails on the deck fronting the golf course. You will love the location and features! Walking distance to spa, The Wintergreen Nature Foundation, and Fire & Frost. Convenient to slopes, Chestnut Springs pool and Upper Shamokin Falls. A great place to relax after a full day of hitting nearby slopes or hiking trails, and exploring Nelson 151's winery and brewery attractions. Stairs to access. WiFi!

Studio Apt. in Wine/Brewery Country/on 151
Clean & bright studio apartment with full kitchen & full bath. Less than 1 mile from Blue Mt. Brewery and Flying Fox Vineyard. Cardinal Point Vineyard, Afton Mountain Vineyard, Silverback Distillery, Valley Road Vineyard & Veritas Vineyard all between 2-5 miles away. Right on 151 also known as "alcohol alley". Tons of breweries, distilleries, ciderys & vineyards all up and down the road. The setting is peaceful. Apt. has fiber internet and Apple TV. Pets welcome for 30 dollars per pet.

Lovingston Get-Away Lovingston, VA
Guesthouse for ADULTS ONLY/ NO kids/pets located in Lovingston, VA. There are wineries, breweries, and distilleries. We have the Wintergreen Ski Resort. The Music Festival in October. Crabtree Falls and Humpback Rock for hiking. In Nelson Co., the Blue Ridge Parkway and Skyland Drive began. Nearby is UVa's Rotunda, Monticello, Appomattox, DC, Schuyler (the Waltons). Nelson hosts peach and apple festivals each year. The beautiful foliage to be seen in the fall and winter snowy mountains.

Crabtree Falls Mountain Hollow Guesthouse
Get back to nature in a river front apartment nestled in the Blue Ridge Mountains. Adjacent to the owner's home, above a rarely used garage, the 70-acre well-maintained property offers mountain forests and a pond view with outdoor experiences for star gazing, and campfires. Escape electronic devices to explore area attractions, waterfalls, hiking trails, scenic drives, and fishing. This new rental is craftsman built with wood interior. We also love hosting our other cabin, Parr's Camp.

Blue Ridge Bliss - For family & friends to enjoy!
Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

Luxury Condo: Stunning Slope Views, Sauna, Dogs-Ok
Welcome to the view from above the clouds! Our two-floor penthouse condo right on the ridge at Wintergreen Resort has stunning views of the mountains and ski slopes. On warm days, you can soak in the sun and dine al fresco on the enormous wraparound deck. On chilly nights, there’s a wood-burning fireplace for cozying up. And no matter the weather, you can soothe your muscles in the state-of-the-art infrared sauna. Whether you’re looking for peace or adventure, this is the place!

Mountain View Nest
From the moment you walk in, this condo offers endless opportunities to relax and retreat. The sweeping mountain views over the back deck provide the ideal setting for a romantic getaway, a girls weekend, or much needed time to recharge. This one bedroom/bathroom unit with a king sized bed, fully stocked kitchen, and artistic decor is located on the third floor of the Ledges. It is the perfect location for those who ski, hike, golf, or taste the flavors from local wineries.

The Meadows of White Mountain
A newly finished space with all of the amenities and stylish attributes to have a peaceful and comfortable home away from home. The Meadows of White Mountain sit nestled into the hillside and is central to the areas many attractions. A quiet and private property. The Meadows is comfy and secluded, and in the winter months when the trees are bare the view opens up to the beautiful western mountain range. We look forward to sharing this wonderful space with you!

Loft w/ Seasonal Private Covered Heated Pool
Sneak away to this cozy mountain loft—your perfect couples’ retreat in Virginia’s wine and beer country. Just off Route 29, you’re minutes from vineyards, trails, and local brews. The space is clean, comfy, and made for easy, no-stress stays. Cool off in the private pool (shared with one cottage), then sip something local as the sun sets. Quiet, cute, and calling your name. Need more room? Check out our cottage for up to 6: airbnb.com/l/i33AHeKs
Popular amenities for Wintergreen Resort apartment rentals
Weekly apartment rentals

Laurelwood Hollow: Walk to Ski & Swim

Best Spot on the Wine/Brew Trail!

Cozy 1BR basement with private entry & W/D

Spacious 2 bdrm Apartment with pool!

Cozy Waynesboro Retreat w/ Patio & Washer/Dryer

Sandstone Lodge

2 Bedroom Near Brewery Parkway 151 Downtown

Ski-In/Out on Dobie! Fantastic Views! PupsOK!
Private apartment rentals

Walk to Ski! Spacious and Pup Friendly!

Big Condo*Luxe Baths*Sweeping Views*Walk2Chairlift

Walk to Market/Slopes!

The highland hideaway

Wintergreen Resort Retreat Private Pool for Guests

Spacious 2 bedroom, 2 bath condo w/ full kitchen

Luxury Guest Quarters w/Blue Ridge Mountain Views

Shenandoah Valley Atelier: NEW Waynesboro Loft
Family-friendly apartment rentals

Lovingston Get-Away Lovingston, VA

Best Spot on the Wine/Brew Trail!

Mountain View Nest

Mimosa Farm *no cleaning fee for 2+ day stays*

Earth Room Suite | Quiet Blue Ridge Retreat

Spacious lower level Airbnb! READ SUMMARY!

Endless Mountain Top Views from All The Way Up!

Blue Ridge Bliss - For family & friends to enjoy!
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $201 SGD | $203 SGD | $170 SGD | $167 SGD | $171 SGD | $180 SGD | $180 SGD | $174 SGD | $179 SGD | $166 SGD | $168 SGD | $211 SGD |
| Avg. temp | 2°C | 4°C | 8°C | 14°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 9°C | 4°C |
Quick stats about flat rentals in Wintergreen Resort

Total holiday rentals
Explore 30 holiday rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort holiday rentals start at $116 SGD per night before taxes and fees

Verified guest reviews
Over 1,540 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Wifi availability
30 of Wintergreen Resort holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wintergreen Resort rentals

4.9 Average rating
Wintergreen Resort stays are highly rated by guests – averaging 4.9 out of 5!
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- Early Mountain Winery
- Boonsboro Country Club
- The Plunge Snow Tubing Park
- Amazement Square
- Massanutten Ski Resort
- James Monroe's Highland
- Homestead Ski Slopes
- Chisholm Vineyards at Adventure Farm
- Wintergreen Resort
- Liberty Mountain Snowflex Centre
- Frontier Culture Museum
- Spring Creek Golf Club
- Blenheim Vineyards
- Farmington Country Club
- Birdwood Golf Course
- Cardinal Point Winery
- Glass House Winery
- Burnley Vineyards
- Monticello
- Meriwether Springs Vineyard and Brewery




