
Nelson Area Rentals
- From $277 per night (USD)
VRBO
Roseland Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This 3-bedroom house is perfect for your escape to Roseland. Inside, guests find a nice mix of sleeping options, includi ...
From $277 per night (USD)VRBO
- From $416 per night (USD)
Expedia
Ski-In Ski-Out Blue Ridge Views at Wintergreen Resort
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to Wintergreen Highland Haven, a beautifully renovated 3-bedroom condo offering incredible Blue Ridge M ...
From $416 per night (USD)Expedia
- From $453 per night (USD)
VRBO
Hot Tub, EV charger, 3 bedroom, Game room, Renovated Kitchen, 4 min to slopes
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to The Fern House, your peaceful mountain retreat in the heart of Wintergreen Resort. Nestled among the trees on ...
From $453 per night (USD)VRBO
- From $429 per night (USD)
Expedia
Sunset Views, Hot Tub, and Firepit in Wintergreen!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Ferncliff, an impressive 3 story mountain home in the heart of Wintergreen with year-round sunset views! Enjo ...
From $429 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Cozy County Cottage- Pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom house is perfect for your escape to Afton. Guests will enjoy two king beds and 2 twin beds, making it eas ...
From $385 per night (USD)VRBO
- From $298 per night (USD)
Expedia
Ski in Style @ Sapphire Squirrel
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Adventure awaits at The Sapphire Squirrel in Wintergreen Resort! Located on Squirrel Tree Lane, our cozy 3-bedroom, 2- ...
From $298 per night (USD)Expedia
- From $286 per night (USD)
VRBO
At the Mountain Mist Retreat, we believe that a true getaway starts with a restful night and a seamless morning. Our 5-bedroom, 4-bathroom layout is thoughtfully designed to provide the perfect gathering.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to Wintergreen Mountain Mist Retreat, a newly renovated five-bedroom, four-bath mountain home high in the Blue Ri ...
From $286 per night (USD)VRBO
- From $430 per night (USD)
Expedia
Rockwell Ridge | Inn with Afton Mountain Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Rockwell Ridge Retreat, a refined mountain getaway in the heart of Nelson County—just off Route 151 and steps ...
From $430 per night (USD)Expedia
- From $213 per night (USD)
VRBO
Rockwell Ridge | Garden Suite with Full Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Garden Suite, a beautifully updated studio suite at Rockwell Ridge—just off Route 151 and steps from Veri ...
From $213 per night (USD)VRBO
- From $210 per night (USD)
Expedia
Rockwell Ridge | Dogwood Suite with Clawfoot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Dogwood Suite, a beautifully updated 1-bedroom, 1-bath suite at Rockwell Ridge—just off Route 151 and ste ...
From $210 per night (USD)Expedia
- From $747 per night (USD)
VRBO
Rockwell Ridge | Private Retreat w/ Mountain Views
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 20
Welcome to Rockwell Ridge Retreat—your exclusive private mountain retreat in the heart of Nelson County, just off Route ...
From $747 per night (USD)VRBO
- From $214 per night (USD)
Expedia
Rockwell Ridge | Chestnut Suite with Lux Bathroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Chestnut Suite, a beautifully updated 1-bedroom, 1-bath suite at Rockwell Ridge—just off Route 151 and st ...
From $214 per night (USD)Expedia
- From $708 per night (USD)
VRBO
Rockwell Ridge | Estate with Afton Mountain Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to Rockwell Ridge Estate—your private mountain estate in the heart of Nelson County, just off Route 151 and step ...
From $708 per night (USD)VRBO
- From $542 per night (USD)
Expedia
Rockwell Ridge | Lodge for Your Blue Ridge Getaway
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Rockwell Ridge Lodge, your private Blue Ridge getaway in the heart of Nelson County—just off Route 151 and st ...
From $542 per night (USD)Expedia
- From $672 per night (USD)
VRBO
The Black Walnut - Your Own Private Resort
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to The Black Walnut, a resort unto itself. This sprawling designer-decorated property is over 6000 sq ft on near ...
From $672 per night (USD)VRBO
- From $595 per night (USD)
Expedia
Shenandoah Ridge 04 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Shenandoah Ridge Mountain Retreat Enjoy a relaxing mountain getaway in this spacious 3-bedroom, 3½-bath condo in Shenan ...
From $595 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Tanners Ridge 37 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Charming Mountain Retreat at Wintergreen Resort Enjoy a peaceful escape in this 1-bedroom condo in Tanners Ridge, nestl ...
From $339 per night (USD)VRBO
- From $584 per night (USD)
Expedia
Walk to SKi Slopes and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to Squirrel Away, a charming 3-bedroom chalet just a two-minute walk from Tyro ski access! Spend your ...
From $584 per night (USD)Expedia
- From $390 per night (USD)
VRBO
The Haven at Wintergreen Resort | Luxury 2BR Condo, 2 Kings & Golf View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Haven at Wintergreen Resort is an upscale 2BR/2BA top-floor end-unit condo overlooking the 18th green of Devils Knob ...
From $390 per night (USD)VRBO
- From $105 per night (USD)
VRBO
Inspiring Mtn Views, Cozy 1 Bdrm/Studio 1/4 mile to Shenandoah Pk, Dogs Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Very quiet, serene, peaceful country setting, surrounded by acres of forests. Just 1/4 mile to Shenandoah Park, Appalach ...
From $105 per night (USD)VRBO
- From $228 per night (USD)
VRBO
Cozy Condo in Peaceful Wintergreen Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind in Wintergreen Resort at this gorgeous condo. With two bedrooms featuring a king bed and two queen beds, guests f ...
From $228 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Willow Haven-Charming 2-bedroom cabin in delightful Afton with AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Afton, this brilliant 1-bedroom/1-loft cabin offers guests a cozy retreat with 1 full bed and 1 king bed. Enj ...
From $321 per night (USD)Expedia
- From $548 per night (USD)
VRBO
Eagles Court 41 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Eagles Court Cozy Mountain Retreat Enjoy a cozy mountain escape in this 2-bedroom, 1½-bath condo in Eagles Court at Win ...
From $548 per night (USD)VRBO
- From $505 per night (USD)
Expedia
Overlook 22 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Overlook Cozy Mountain Retreat Enjoy a relaxing mountain getaway in this 2-bedroom, 2-bath condo at Overlook, convenien ...
From $505 per night (USD)Expedia
- From $946 per night (USD)
VRBO
Fore Seasons: 2 Homes + Game Room | Nelson 151
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 14
MAIN HOUSE (sleeps 8): The first floor features a living room with smart TV, fully stocked kitchen, formal dining space, ...
From $946 per night (USD)VRBO
- From $965 per night (USD)
VRBO
The Mountain House at 12 Ridges Vineyard, unparalleled escape
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Perched high above Virginia’s Blue Ridge Mountains, The Mountain House at 12 Ridges Vineyard offers an unforgettable lux ...
From $965 per night (USD)VRBO
- From $81 per night (USD)
VRBO
Peaceful, Luxury Studio/1 Bdrm. w/Expansive Blue Ridge Mtn. Views. Dog Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*FALL SPECIAL: $150 BONUS TO YOU! *Serene, quiet setting with stunning Mountain Views just 3 minutes to I-64. *Built i ...
From $81 per night (USD)VRBO
- From $564 per night (USD)
Expedia
Prime Location! 5 Min to National Park & Wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Escape to Afton Ridge Cabin, a newly renovated mountain retreat in the Blue Ridge Mountains. Enjoy stunning pa ...
From $564 per night (USD)Expedia
- From $683 per night (USD)
VRBO
Private Mountain Getaway Wintergreen Resort
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
Summary: Unplug and unwind at 'Sunny Bear 'at Wintergreen Resort, VA. A peaceful mountain retreat tucked away yet close ...
From $683 per night (USD)VRBO
- From $445 per night (USD)
Expedia
Relaxing Wintergreen Mountain Home-close to the ski slopes, hiking, hanging out
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy mountain retreat in Wintergreen Resort, near the Appalachian Trail, and 30+ miles of Wintergreen Nature trails. Clo ...
From $445 per night (USD)Expedia
- From $424 per night (USD)
VRBO
Pickleball - Hot Tub - River/Hike - 4 King Beds
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to your private luxury retreat-where upscale comfort meets the beauty of the outdoors. Tucked far off the beaten ...
From $424 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Oasis in the Blue Ridge Rt. 151 Brew Ridge Trail-Cozy Cottage in the mountains
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to the Glass Hollow Cottage! Come make yourself at home and enjoy the rustic charm of our custom hand-built cott ...
From $180 per night (USD)Expedia
- From $248 per night (USD)
VRBO
Cabin Charm in the Blue Ridge Mountains/151 Brew Ridge Trail in secluded hollow
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Welcome to the Glass Hollow Cabin! Come make yourself at home & enjoy the rustic charm of our beautiful newly renovated ...
From $248 per night (USD)VRBO
- From $381 per night (USD)
Expedia
Pet-Friendly Retreat Walk to Slopes & Village!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Bear Paw is a newly renovated, pet friendly two bedroom, two bath condo located in the Three Ridges community ...
From $381 per night (USD)Expedia
- From $906 per night (USD)
VRBO
LuxuryIHot tubISaunaICold PlungeIGame RoomIViews
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Luxury 4100+ sqft designer resort-style home in Wintergreen with top and unique amenities: • 6 bedrooms, 4.5 baths, 12 ...
From $906 per night (USD)VRBO
- From $529 per night (USD)
VRBO
5-star property in Wintergreen Resort under new management!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Stay close to the mountain lodge and all the best activities the mountains and Wintergreen Resort has to offer! The clas ...
From $529 per night (USD)VRBO
- From $623 per night (USD)
VRBO
Mountain Retreat: Year-Round Getaway, Pup Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy mountain home just 4 minutes from the slopes with 3 bedrooms (2 kings, 1 queen), 2 full bathrooms, a large stone fi ...
From $623 per night (USD)VRBO
- From $372 per night (USD)
Expedia
Modern Farmhouse w/ Hot Tub, Yard. Pet Friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Tupelo, a designer-decorated Blue Ridge home on one acre at the base of the mountain. Located between the Blu ...
From $372 per night (USD)Expedia
- From $353 per night (USD)
VRBO
Tranquil Vacation Rental Nestled in the Shenandoah Mountains of Howardsville, Virginia
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This peaceful vacation rental is nestled in the foothills of the magnificent Shenandoah Mountains in Howardsville, Virgi ...
From $353 per night (USD)VRBO
- From $744 per night (USD)
Expedia
Shenandoah Ridge 05 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Shenandoah Ridge Spacious Mountain Escape Escape to the mountains in this spacious 4-bedroom, 4-bath condo at Shenandoa ...
From $744 per night (USD)Expedia
- From $744 per night (USD)
VRBO
Shenandoah Ridge 27 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Stonewall Court Spacious Mountain Retreat Enjoy a spacious mountain getaway in this inviting 4-bedroom, 4-bath condo at ...
From $744 per night (USD)VRBO
- From $252 per night (USD)
VRBO
Wintergreen Couples Retreat: Fireplace, Hiking, Wineries & Blue Ridge Parkway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to the Blue Ridge Mountains and unwind in this cozy 1-bedroom Wintergreen retreat, perfect for couples, anniversa ...
From $252 per night (USD)VRBO
- From $951 per night (USD)
VRBO
Wildbriar Lodge • Luxe 6BR, 6,100 SqFt • Theater, 2xGameRoom, Karaoke, Sleeps 22
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 22
Welcome to Wildbriar Lodge at Wintergreen Resort, hosted by Getawaypad. NEW LISTING!!! NEWLY RENOVATED! WEEKLY DISCOUN ...
From $951 per night (USD)VRBO
- From $943 per night (USD)
Expedia
Brew Trail Retreat: Hot Tub, Scenic Mountain Views, Game Rooms, Pet&Kid Friendly
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to your private mountain retreat in Nellysford, a spacious 6-bedroom, 4.5 bath escape designed for unforgettable ...
From $943 per night (USD)Expedia
- From $330 per night (USD)
VRBO
Hot Tub | King Suites | Outdoor Fireplace & Lounge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Highland House—your private retreat nestled among rolling hills, sweeping farm views, and the kind of qui ...
From $330 per night (USD)VRBO
- From $348 per night (USD)
Expedia
Farmhouse Central to Nelson 151 + Walk to Brewery!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come explore the Blue Ridge Mountains in style at this elegantly designed Afton farmhouse, complete with wooded views, a ...
From $348 per night (USD)Expedia
- From $668 per night (USD)
VRBO
The Vineyard House at 12 Ridges Vineyard, breathtaking views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in the heart of 12 Ridges Vineyard, this stunning vineyard house offers a one-of-a-kind Blue Ridge Mountain esca ...
From $668 per night (USD)VRBO
- From $736 per night (USD)
Expedia
Gorgeous 4-bedroom penthouse condo with building elevator at Wintergreen!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the beauty of Roseland from this fabulous 4-bedroom condo. With three king beds and one queen bed, guests find ...
From $736 per night (USD)Expedia
- From $627 per night (USD)
VRBO
Luxury Mountain Cabin Rental on Rockfish Gap River near Charlottesville, Virginia
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This luxury mountain cabin rental is located on the Rockfish Gap River in Nellysford—the perfect location for a getaway ...
From $627 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Stylish Mountain Retreat Close to Trails & Tastings
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
"Mountain Memories" is our cozy, renovated chalet that is just a 5-minute walk to the slopes, lodge, and dining. The tra ...
From $299 per night (USD)VRBO
- From $923 per night (USD)
VRBO
Gorgeous Views. Resort-Style Amenities Await
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to Loves Afton Cabin! Gather your loved ones and escape to our secluded 17.5-acre retreat, with breathtaking mou ...
From $923 per night (USD)VRBO
- From $379 per night (USD)
Expedia
Spacious 3 Br • Hot Tub • Easy Wine Country Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Note: You'll have the entire property to yourself. This listing is for the upper floor. There is also a 6BR full-house l ...
From $379 per night (USD)Expedia
- From $189 per night (USD)
VRBO
Ideal Location: 1-bedroom condo. Top of Wintergreen Resort. Easy walk all around
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This comfortable 1 bedroom (king size bed) 1 bathroom condo has everything you need to enjoy your stay in the Blue Ridge ...
From $189 per night (USD)VRBO
- From $449 per night (USD)
Expedia
Welcome to Serenity Slope! Wintergreen Resort 4 bd 2 ba home-great all seasons!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
As you enter the inviting foyer, it opens up to 3 bedrooms with TVs and charging stations in each room. There is also a ...
From $449 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Fairway Woods 25 With Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fairways Woods Mountain Getaway Escape to the mountains in this 2-bedroom, 2-bath condo in Fairways Woods, nestled in W ...
From $465 per night (USD)VRBO
- From $521 per night (USD)
VRBO
The perfect Blue Ridge mountain getaway awaits at Wintergreen resort!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your perfect mountain getaway at Wintergreen Resort! Nestled in the Blue Ridge Mountains, our home offers an ...
From $521 per night (USD)VRBO
- From $716 per night (USD)
VRBO
Brand-New Listing! Newly Updated 4BR/4BA Condo with Stunning Mountain Views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to your mountain retreat at Wintergreen Resort! This newly updated 4-bedroom, 4-bathroom condo offers stunning m ...
From $716 per night (USD)VRBO
- From $433 per night (USD)
Expedia
Luxury Stay w/ Fenced Yard, Hot Tub, Mountain View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sleeps 4 | Dog Friendly | NEW Hot Tub | Fire Pit OFFICE - Queen sleeper sofa (linen & pillows provided) and desk with o ...
From $433 per night (USD)Expedia
- From $619 per night (USD)
VRBO
Luxury Ski-in/Ski-out Chalet with Mountain Views at Wintergreen Resort
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Alpine Ascent – Luxury Ski-In/Ski-Out Chalet with Mountain Views at Wintergreen Resort Welcome to Alpine Ascent, where ...
From $619 per night (USD)VRBO
- From $1094 per night (USD)
Expedia
Afton Peak
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Summary: Discover AFTON PEAK, a brand-new luxury A-Frame designed for unforgettable mountain getaways! Don’t let this A ...
From $1094 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Hilltop Hideaway - Wintergreen 5BR with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Hilltop Hideaway! Located in the heart of Wintergreen, Hilltop Hideaway features a hot tub, 2 propane firepit ...
From $500 per night (USD)VRBO
- From $424 per night (USD)
Expedia
Fall in Love in this Cute Cabin Rental with for Two in Love, Virginia
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Named after the nearby summit beside Three Ridges, Bee Mountain is a cozy open-plan cabin perfect for couples. Relax in ...
From $424 per night (USD)Expedia
- From $725 per night (USD)
VRBO
Dobie 21 With Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Dobie Mountain Retreat Settle into a comfortable mountain escape in this spacious 3-bedroom, 3-bath condo at Dobie, con ...
From $725 per night (USD)VRBO
- From $755 per night (USD)
Expedia
Experience luxury mountain living with breathtaking Blue Ridge views, a hidden speakeasy, hot tub, fire pit, and premium amenities just minutes from Skyline Drive, Shenandoah National Park, and Nelson 151.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perched atop the Blue Ridge above Nelson County, Skyline Retreat is built around the view. Guests come for panoramic vis ...
From $755 per night (USD)Expedia
- From $524 per night (USD)
VRBO
Modern cabin, hot tub, mtn views, fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Ash House is a modern cabin located on Route 151 in Nelson County, close to Wintergreen Resort, Shenandoah National ...
From $524 per night (USD)VRBO
- From $541 per night (USD)
Expedia
Grand Wintergreen Resort Home w/ Hot Tub!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
3,450 Sq Ft | Game Room | Blue Ridge Parkway & National Forest Access Behind Home Year-round mountain fun awaits at thi ...
From $541 per night (USD)Expedia
- From $979 per night (USD)
VRBO
Escape to Breathtaking View Retreat at Wintergreen a stunning 3-bedroom, 4-bath mountain home with three incredible decks, cozy fireplace, grill and patio area, and breathtaking Blue Ridge views perfect for families and kids!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Welcome to Breathtaking View Retreat at Wintergreen, where mountain elegance meets peace and fun for all ages. This spac ...
From $979 per night (USD)VRBO
- From $309 per night (USD)
Expedia
Designer Look: Mountain View Pool Tennis One Level
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 10
SINGLE LEVEL home, no steps. Our contemporary mountain homestead sits amidst aboral oasis with mountain views. Work remo ...
From $309 per night (USD)Expedia
- From $250 per night (USD)
VRBO
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nestled in Wintergreen Resort, this delightful studio condo offers a perfect retreat for guests. Enjoy a fully stocked k ...
From $250 per night (USD)VRBO
- From $348 per night (USD)
Expedia
Beautiful 3 Bedroom Mountain House Private Sauna and Hottub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled among the trees, The Bear’s Perch is a cozy treetop retreat with a stone fireplace, spacious decks, and forest v ...
From $348 per night (USD)Expedia
- From $595 per night (USD)
VRBO
Rock Climb Wall, “Treehouse” Suite, Hot Tub, Blue Ridge Views, Sleeps 14
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Escape to the mountains at this 5BR/4.5BA home in Wintergreen Resort! Enjoy breathtaking Blue Ridge Mountain views, cozy ...
From $595 per night (USD)VRBO
- From $820 per night (USD)
Expedia
New! Secluded Farmhouse Pool + Firepit 14ppl
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Halfmoon Farmhouse – Luxury 6-Bedroom Mountain Retreat Near Charlottesville & Nelson 151 Welcome to Halfmoon Farmhouse, ...
From $820 per night (USD)Expedia
- From $388 per night (USD)
VRBO
Wintergreen cabin, hot tub, sauna, walk to trails
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Modern Mountain Retreat in Wintergreen Resort Walkable to the park, seasonal pool, and trails - The home's located direc ...
From $388 per night (USD)VRBO
- From $209 per night (USD)
Expedia
Amazing views! Wintergreen ground-level condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Vista Haus, a cozy 1BR / 1BA condo in the Cliffs condos at Wintergreen. The Cliffs are known for their amazin ...
From $209 per night (USD)Expedia
- From $392 per night (USD)
VRBO
Firefly on The Ridge: Mountain + Ski Slope Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled high in the Blue Ridge Mountains, this condo is ideally located within Wintergreen Resort, one of Virginia’s pre ...
From $392 per night (USD)VRBO
- From $347 per night (USD)
Expedia
Stoneridge 35 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stoneridge Mountain Escape Relax and recharge in this 2-bedroom, 2-bath condo in Stoneridge, located in Wintergreen's s ...
From $347 per night (USD)Expedia
- From $934 per night (USD)
VRBO
Oh Deer NEW LUXURY-renovated, hot tub/sauna, views
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
OH DEER! Welcome to your perfect escape in the Blue Ridge Mountains! Nestled just steps from the slopes of Wintergreen S ...
From $934 per night (USD)VRBO
- From $465 per night (USD)
Expedia
Secluded Mountain Cottage in Virginia Wine Country
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the heart of the Blue Ridge Mountains, this secluded mountain cottage offers the perfect balance of rustic ch ...
From $465 per night (USD)Expedia
- From $250 per night (USD)
VRBO
First Floor Slope Side Wintergreen Condo – Ski In / Ski Out
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Wake up to mountain views, falling snow, or rolling mist at Little Mountain Haven. Enjoy true ski-in/ski-out access with ...
From $250 per night (USD)VRBO
- From $819 per night (USD)
Expedia
Spectacular Mountain Views • Two Decks • Three Living Spaces • 1/2 Mi to slopes
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Traveling with a large group doesn't have to mean sacrificing privacy. Our 3,900-square-foot Wintergreen home has six tr ...
From $819 per night (USD)Expedia
- From $783 per night (USD)
VRBO
Spacious Mountain Escape | Pool, Spa | Sleeps 14 | Pets OK | Near Wineries |Game Room
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Tucked away in the mountains of Afton VA, this secluded 6BR retreat is designed for slow weekends, group getaways, and c ...
From $783 per night (USD)VRBO
- From $471 per night (USD)
Expedia
Wintergreen 5BR w/ Hot Tub, Sauna. Walk to slopes!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to Tyro Slopeside Vista! This chalet is located in the heart of Wintergreen, and literally across the street fro ...
From $471 per night (USD)Expedia
- From $309 per night (USD)
VRBO
Artisan's Cottage: Woodsy+Private, Central to 151
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
🛌 Sleeps 4 | 🛁 1 Bathroom | 🔥 Fire Pit | 🍷🍺 Central to Wineries & Breweries Artisan's Cottage is located at the e ...
From $309 per night (USD)VRBO
- From $621 per night (USD)
Expedia
Family Time in Love, Virginia: Mountain Cabin Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This rental's large windows and mountain views of Wintergreen and the Three Ridges Wilderness Area are the perfect place ...
From $621 per night (USD)Expedia
- From $453 per night (USD)
VRBO
Romantic Glamping Getaway in Love, Virginia's Natural Beauty
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This rental is an open floor plan cabin with a king bed in the sleeping area and a jetted tub by the gas fireplace in th ...
From $453 per night (USD)VRBO
- From $380 per night (USD)
VRBO
The Fairway Chalet / 2 BR + Loft
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our newly renovated mountain home on Wintergreen’s golf course is minutes from the slopes, trails, and breweries. Relax ...
From $380 per night (USD)VRBO
- From $317 per night (USD)
VRBO
Barrel Sauna, Hot Tub & Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the perfect quiet getaway right off the Nelson 151 Brew Trail. This stunning 1891 farmhouse has been renovate ...
From $317 per night (USD)VRBO
- From $369 per night (USD)
Expedia
Your Ski-In and Ski-Out Wintergreen Escape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Stay at Mountain Mama, a prime ski-in/ski-out condo on Eagles Swoop at Wintergreen Resort. Enjoy direct slope ...
From $369 per night (USD)Expedia
- From $670 per night (USD)
VRBO
Spacious Mountain Family Retreat-Hot Tub & Game Room
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to this spacious 5 bedroom 3 bath home located in the heart of Wintergreen, less than a mile from skiing and clo ...
From $670 per night (USD)VRBO
- From $775 per night (USD)
Expedia
Swannanoa Guest House: Stunnning Mountain Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Discover the perfect blend of modern comfort and scenic tranquility in this beautifully renovated 5-bedroom, 5-bathroom ...
From $775 per night (USD)Expedia
- From $407 per night (USD)
VRBO
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to the Swiss Chalet at Wintergreen Resort! A top-floor Laurelwood condo — one of the most walkable locations on ...
From $407 per night (USD)VRBO
- From $410 per night (USD)
Expedia
Sunrise Cabin, Centrally Located 4BR + Dog-Friendly, Sleeps 11
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to this cozy mountain cabin right in the heart of Wintergreen Resort with easy access to ski lifts, Discovery Rid ...
From $410 per night (USD)Expedia
- From $440 per night (USD)
VRBO
TRUE SKI OUT Condo Sleeps 2-5 on Eagles Swoop at Wintergreen Resort.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This 2-bedroom condo is perfect for your escape to Wintergreen Resort. Conveniently located in walking distance to the S ...
From $440 per night (USD)VRBO
- From $323 per night (USD)
Expedia
Walk to Slopes & Village at Wintergreen Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Fox Paw is a pet-friendly two-bedroom, two-bath condo nestled in the Three Ridges community at Wintergreen Res ...
From $323 per night (USD)Expedia
- From $384 per night (USD)
VRBO
2BR Bear Haven at Wintergreen - Pool Access, Hiking & Blue Ridge Fun
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Bear Haven at Wintergreen! Escape to the Blue Ridge Mountains and enjoy a relaxing stay in this updated 2-be ...
From $384 per night (USD)VRBO
- From $540 per night (USD)
Expedia
Forever Farm: Private Mtn Estate in Wine Country
- Bedrooms:
- 0
- Bathrooms:
- 3
- Sleeps:
- 8
FIRST FLOOR - Open-concept kitchen, dining area, and living room - Powder room - Laundry room with utility sink (dete ...
From $540 per night (USD)Expedia
- From $371 per night (USD)
VRBO
The Retreat at Afton Mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to the foothills of the Blue Ridge Mountains and be in the heart of it all! Stay across the street from Veritas ...
From $371 per night (USD)VRBO
- From $449 per night (USD)
Expedia
3BD & 3BA, Golf Access | Sleeps 12 | Pets OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
✨ Luxury Mountain Getaway in Wintergreen | Stoney Creek Golf Access | Sleeps 12 | Pet-Friendly Welcome to a spacious mou ...
From $449 per night (USD)Expedia
- Click For Pricing
VRBO
Original 1798 Antique Appalachian Chestnut log cabin- \"Annies Cabin\"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This adorable antique Appalachian log cabin was built by Thomas Jeffersons nephew, Peter Carr in 1798 and is made comple ...
Click For PricingVRBO
- From $418 per night (USD)
VRBO
Lovely 2-bedroom cottage in charming Wintergreen Ski Resort Community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Secluded woodland retreat with a private hot tub and peaceful views within the Stoney Creek section of Wintergreen. This ...
From $418 per night (USD)VRBO




































































































