Blue Ridge Mountains at Wintergreen Resort
📍 Wintergreen Resort, Virginia

Your Blue Ridge Mountain Escape

Three exceptional mountain properties — from cozy cabin getaways to a luxury 9-bedroom estate sleeping 24+.

3 Listings
2+2 Hot Tubs & Saunas
★ 5 Star Rated
Find Your Perfect Mountain Retreat
All properties are located at Wintergreen Resort in the Blue Ridge Mountains of Virginia, with easy access to hiking, skiing, wineries, and more.
⭐ Featured Estate
Blue Ridge Bliss
Blue Ridge Bliss
Luxury 2-Home Mountain Estate
🛏 9 BR
🚿 6 BA
👥 Up to 24
$900 – $3,000 / night
  • Two private homes, 20 seconds apart — perfect for reunions & retreats
  • 2 hot tubs, 2 saunas, 3 fireplaces & 2 full game rooms
  • 2 EV chargers, pet-friendly, summer pool access
🏡 Sleeps 16+
Pleasant Point
Pleasant Point
Forest Spa Chalet with Hot Tub & Sauna
🛏 6 BR
🚿 4 BA
👥 Up to 16
$400 – $2,000 / night
  • Designer spa chalet — hot tub & sauna with a TV you can watch from the water
  • Bunk room with slide, game room with arcade, shuffleboard & NES
  • Soaking jet tub with its own TV, pizza oven & firepit under the stars
🌲 Cozy Cabin
Quisi South
Quisi South
Forest Cabin Getaway: Hike, Soak, Play
🛏 3 BR
🚿 2 BA
👥 Up to 7
$150 – $1,000 / night
  • Upscale cabin with outdoor hot tub & sauna beneath the forest canopy
  • Multiple decks with firepit under the stars & screened game room
  • Wood-burning fireplace, soaring ceilings, 5 min to skiing
Skip the Booking Fees
Booking directly with us gives you the best experience — and often a better rate than OTA platforms.
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No OTA Surcharges

Avoid the 10–15% platform fees charged by Airbnb and VRBO when you book directly with us.

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Direct Host Access

Communicate directly with your host for faster responses and personalized recommendations.

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Secure Booking

Our booking system is powered by Hospitable — trusted, encrypted, and professionally managed.

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Flexible Policies

Pet-friendly (up to 2 dogs under 50 lbs). EV charging at both homes. Easy keyless check-in.

Wintergreen Resort, Virginia

Nestled in the Blue Ridge Mountains, Wintergreen Resort offers a rare combination of mountain adventure and peaceful retreat — all within a 2.5-hour drive from Washington DC, Charlotte, and Richmond.

⛷️ Skiing & Snow Tubing
🥾 Mountain Hiking
🍷 Wineries & Breweries
⛳ Championship Golf
🏊 Lake Monocan Beach
🧘 Spa & Wellness
🌿 Blue Ridge Parkway
🎣 Fishing & Kayaking
Wintergreen area
What To Do Around Wintergreen
World-class wineries, craft breweries, and epic mountain hikes — all within 30 minutes of your door.
01
Devil's Backbone Basecamp Brewpub

Virginia's most celebrated craft brewery, and their Basecamp Brewpub in the Meadows is just minutes away. Outdoor seating, live music, award-winning lagers, and a full kitchen. The Vienna Lager alone is worth the drive.

Visit website →
02
Three Notch'd Brewing — Rockfish Gap

A neighborhood brewery with serious craft cred. The Rockfish Gap outpost features a rotating tap list, food trucks, and a laid-back vibe. Great spot to decompress after a hike on the Blue Ridge Parkway.

Visit website →
03
Bold Rock Cidery — Nellysford

One of the East Coast's premier hard cideries, set on a 200-acre farm in Nellysford. Beautiful taproom, scenic views, and a full range of dry to semi-sweet ciders made from local Virginia apples. Stunning in fall.

Visit website →
04
Blue Toad Hard Cider

A cozy cidery tucked into the Blue Ridge foothills, known for small-batch craft ciders made from Virginia apples. Friendly, low-key, and a great find for cider lovers looking to get off the beaten path.

Visit website →
05
Blue Mountain Brewery

Perched at 2,000 feet with panoramic mountain views, Blue Mountain's brewery and farm are a must. The barrel house produces some of Virginia's finest farmhouse ales. The view from the deck is reason enough to visit.

Visit website →
01
Veritas Vineyard & Winery

The crown jewel of Nelson County wine country. Award-winning wines, a stunning mountain backdrop, and a farm-to-table restaurant worth a reservation on its own. Their Cabernet Franc and Petit Manseng are exceptional.

Visit website →
02
Afton Mountain Vineyards

One of Virginia's oldest and most respected wineries, with vines producing since the 1970s. The setting is classic Blue Ridge — pastoral, unhurried, and authentic. Their Gewürztraminer is a local favorite.

Visit website →
03
Hazy Mountain Vineyards

A boutique winery in the Blue Ridge foothills with a relaxed, off-the-beaten-path feel. Small-batch wines and breathtaking mountain views make this a hidden gem worth seeking out.

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04
Hill Top Berry Farm Winery & Meadery

Something truly unique — a family farm producing fruit wines, berry wines, and honeymead alongside traditional varietals. A charming stop for those who want to venture beyond the mainstream wine trail.

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05
Valley Road Vineyards

A farm winery with the kind of unhurried, welcoming atmosphere that makes Virginia wine country special. Great for a relaxed afternoon tasting with sweeping views of the Blue Ridge foothills.

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01
Crabtree Falls

Virginia's tallest cascading waterfall — five major cascades dropping 1,200 feet total. Observation platforms at each level. Lower falls are family-friendly; the full upper trail is a serious workout. One of the most beautiful hikes in the state. 11 miles from Wintergreen.

View on AllTrails →
02
Blue Ridge Tunnel

Walk through a 100-year-old railroad tunnel bored straight through the Blue Ridge Mountains — a one-of-a-kind experience. The historic 1,000-foot tunnel is dramatic, cool, and unlike anything else in the region. Accessible for all ages and abilities. Bring a flashlight.

Visit website →
03
Humpback Rocks

The most popular hike on the entire Blue Ridge Parkway. A steep but short 2-mile climb to a rocky summit with one of the most dramatic 360° panoramas in Virginia. Sunrise and sunset hikes are legendary. 20 minutes from Wintergreen.

View on AllTrails →
04
Spy Rock

A hidden gem with arguably the best summit view in the area — a bare rock perch on the AT with 360° views of the Shenandoah Valley, Three Ridges, and The Priest. Long but gentle grade. The one locals bring out-of-state guests for the "wow" moment.

View on AllTrails →
05
Wintergreen Resort Trails

30+ miles of maintained trails right on the mountain — step out the door and hike. From gentle morning nature walks to ridge hikes with views. Perfect for families or anyone who wants to hike before breakfast and be back in time for the hot tub.

View trail map →
Welcome to Pleasant Point
Where It All Began

We're Chris and Bianca, and every one of our properties carries a piece of our story.

We met in 2001 at a resort in Maine called Quisisana — much like the one in Dirty Dancing. Bianca was an opera singer, Chris worked in the kitchen, and we fell in love instantly. In 2007, we married at Pleasant Point resort, right next door.

Those names have stayed with us: the house we later purchased became Quisi South (a nod to Quisisana), and when we added the property across the street in 2024, it was a natural fit to call it Pleasant Point. Together they became Blue Ridge Bliss.

Not singing opera anymore, but still using her voice — if you're an RVA native, you may recognize Bianca as the Richmond Flying Squirrels PA Announcer. And if you look carefully around Pleasant Point, you might spot a few hidden squirrels she left just for you. 🐿️

We hope you create your own memories here, just as we did.

— Chris & Bianca
Owners, Wintergreen Vacation Rental