
Nelson Area Rentals
- From $189 per night (USD)
VRBO
Wintergreen Resort Condo w/ Deck, 0.3 Mi to Slopes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Plan for plenty of outdoor fun when you stay at this Wintergreen Resort vacation rental! With a vibrant interior, privat ...
From $189 per night (USD)VRBO
- From $206 per night (USD)
VRBO
- NEW - Spruce Creek Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Relax with the whole family at this peaceful cottage nestled in the heart of the blue ridge mountains. Short distance to ...
From $206 per night (USD)VRBO
- From $222 per night (USD)
VRBO
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Step into the allure of our fantastic Wintergreen near-slope condo, just a leisurely 4-min stroll away from the heart of ...
From $222 per night (USD)VRBO
- From $354 per night (USD)
Expedia
All-Season Fun! Wintergreen Resort Condo w/ Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 15
Rare find! True ski-in/ski-out at Wintergreen Resort! Make the most of your next Virginia mountain getaway at Slipper Sl ...
From $354 per night (USD)Expedia
- From $471 per night (USD)
VRBO
Blackwood Chalet: Hot Tub + 0.3 mile from Slopes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
OUTDOORS: Private deck with hot tub, propane fire pit (4 chairs), and front porch ski closet. INDOORS: *NEW* 55" Roku S ...
From $471 per night (USD)VRBO
- From $1173 per night (USD)
Expedia
New! Farmhouse Epic Covered Porch FirePit
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Extremely Secluded! 320 acres of trails, streams, fishing pond, and relaxation. Reconnect with family and friends. Hig ...
From $1173 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Blue's Barn: Central to Wineries & Breweries
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
DOWNSTAIRS: Dining Room: counter height dining table with 4 stools Living Room: queen sleeper sofa, two side chairs, ...
From $313 per night (USD)VRBO
- From $340 per night (USD)
Expedia
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
2min drive to Wintergreen skiing. Modern-meets-mountain vibe in this 4-season chalet nestled in the treetops. Hot tub, ...
From $340 per night (USD)Expedia
- From $499 per night (USD)
VRBO
Spacious, private, four-season mountainside home close to Wintergreen and hiking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 17
Three Ridges is a spacious, private, four-season, mountain-side home with 21 acres on the quiet side of Nelson County. A ...
From $499 per night (USD)VRBO
- From $634 per night (USD)
Expedia
Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to "Above the Clouds", your year-round retreat in the heart of Wintergreen. Our spacious house, nestled just min ...
From $634 per night (USD)Expedia
- From $297 per night (USD)
VRBO
The Cottage @ Afton Mountain- Close to Wineries!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Cottage at Afton Mountain! Located in the heart of 151 Wine Country, just one minute from Veritas and th ...
From $297 per night (USD)VRBO
- From $374 per night (USD)
Expedia
Twin Ponds: King Beds, Hot tub, Gameroom, 75\" TV, Foosball, Air Hockey, PingPong
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
About this space Welcome to Twin Ponds, a beautifully appointed & fun-filled mountain house in Wintergreen Resort's Ston ...
From $374 per night (USD)Expedia
- From $627 per night (USD)
VRBO
Escape the Heat • 10° Cooler Mtn Oasis • Hot Tub • Fire Pit • 4 Ensuite BRs
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PROPERTY OVERVIEW: Escape the summer heat at 3,800 feet in the Blue Ridge Mountains! Often up to 10° cooler than the va ...
From $627 per night (USD)VRBO
- From $238 per night (USD)
Expedia
Wintergreen Ski Resort Condo w/ Golf Access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Days spent shredding the slopes and cozy nights by the fireplace await when you stay at this charming 2-bedroom, 2-bathr ...
From $238 per night (USD)Expedia
- From $355 per night (USD)
VRBO
Wintergreen Resort Getaway w/ Deck, Mountain View!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
Enjoy easy access to all of the excitement Wintergreen Resort has to offer at this charming Roseland vacation rental! Lo ...
From $355 per night (USD)VRBO
- From $646 per night (USD)
Expedia
The Brew Ridge Trail's Most Unique Home. Sleeps 12
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Surely you've heard about the "Almost World-Famous Boogie Nights Manor". The Boog has remained the #1 rated STR property ...
From $646 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Walking Distance to Ski Slopes! Cozy Condo that sleeps 4!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just 3-5 minutes walk to the Slopes, Ski Check in, the Market, Restaurants, Shops and Entertainment, our newly renovated ...
From $214 per night (USD)VRBO
- From $1378 per night (USD)
Expedia
Heaven On Earth ~ Wintergreen Mountain
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Nestled amid the pristine beauty of the towering mountains, Heaven On Earth provides the perfect alpine escape for those ...
From $1378 per night (USD)Expedia
- Click For Pricing
VRBO
Wintergreen Oasis - PRIVATE POOL & SAUNA
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
This Wintergreen Oasis is a private home nestled in the Stoney Creek area of Wintergreen Resort. This 1.3 acre property ...
Click For PricingVRBO
- Click For Pricing
Expedia
The Wintergreen Treehouse
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Relax and enjoy your time secluded in nature on roughly four acres of land right down the road from Paul's Creek, many h ...
Click For PricingExpedia
- From $654 per night (USD)
VRBO
Hot Tub & Views | Mid Century Modern Wonder
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Welcome to this beautiful, mid-century modern mountain home! You will fall in love with the open floor plan, chef’s kitc ...
From $654 per night (USD)VRBO
- From $1474 per night (USD)
Expedia
Dream Big in the Blue Ridge Mountains
- Bedrooms:
- 8
- Bathrooms:
- 10
- Sleeps:
- 25
Bring everybody together in our Blue Ridge Mountain 10,000 square foot home. The home is located in Nellysford`s Stoney ...
From $1474 per night (USD)Expedia
- Click For Pricing
VRBO
Graceland - A Magnificent Estate on 14 Acres
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
This 14 Acre private estate is designed and built with the highest quality materials and thoughtfulness in every square ...
Click For PricingVRBO
- From $302 per night (USD)
Expedia
The Blue Llama | Pets OK | Llama Loft | Fire Pit | Fenced Yard | Off Nelson 151
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to our blue-tiful Blue Llama vacation rental located at the heart of Nelson County in Nellysford, Virginia. Insp ...
From $302 per night (USD)Expedia
- From $618 per night (USD)
VRBO
100 FT to SLOPES! 4bd 3bth Ski-in ski- out Dobie Condo - walk to Mountain Inn
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Best Location! Year-round - walk to Mountain Inn Ski-In/Ski-Out Slopeside family-sized Dobie Condo with loft RIGHT NEXT ...
From $618 per night (USD)VRBO
- From $398 per night (USD)
Expedia
Relax in a charming cottage near Nelson 151 featuring a private hot tub, cozy gathering spaces, and easy access to Virginia's wineries, breweries, hiking trails, and Blue Ridge scenery.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Papa’s Cottage is a private two-bedroom home in Afton, Virginia, offering a comfortable and relaxed stay near Nelson 151 ...
From $398 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Relax in a charming cottage near Nelson 151 featuring inviting living spaces and easy access to Virginia's wineries, breweries, hiking trails, and beautiful Blue Ridge scenery.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in Virginia wine country, Meme’s Cottage is a peaceful Afton getaway designed for relaxing stays near Nelson 151 ...
From $365 per night (USD)VRBO
- From $385 per night (USD)
Expedia
Hot Tub Pool Pac Man Foosball Dogs OK Tennis Golf
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
4min to ski, walk to trails! Endless activities: apple picking, breweries/wineries, hiking, lake, horseback, golf, tenni ...
From $385 per night (USD)Expedia
- From $460 per night (USD)
VRBO
Hot Tub Sauna EV Charger Golden Tee Pool Tennis
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
5min to ski slopes! New hot tub and EV charger. Perfect for 2-3 families. After day of adventures, gather for sunset on ...
From $460 per night (USD)VRBO
- From $404 per night (USD)
Expedia
Sip 'n Dip: Hot Tub Foosball Pool Table Ping Pong
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Easy access to Wintergreen Resort, hiking trails, tennis, golf, and breweries/wineries. Great for families and groups. ...
From $404 per night (USD)Expedia
- From $676 per night (USD)
VRBO
Cozy House at Wintergreen with hot tub/firepit/fireplace & all amenities included and pool access!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our cozy 4-bedroom, 3.5-bathroom home in Wintergreen Resort, VA. Enjoy a spacious living room with a fireplac ...
From $676 per night (USD)VRBO
- From $702 per night (USD)
VRBO
Historic Farm Renovated with Comfort, Mountain Views, Hot Tub, Pond, & Animals!
- Bedrooms:
- 8
- Bathrooms:
- 11
- Sleeps:
- 26
Lovingly maintained and beautifully updated, this 1840s farmhouse is the treasure you’ve been looking for! Every room is ...
From $702 per night (USD)VRBO
- From $487 per night (USD)
VRBO
Cozy Wintergreen Ski Chalet -hot tub-Walk to slopes & family friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "The Brown Bear Lodge", your year-round retreat in the heart of Wintergreen Ski Resort- just a short walk fro ...
From $487 per night (USD)VRBO
- From $1820 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 12
- Bathrooms:
- 11
- Sleeps:
- 30
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $1820 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $359 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $359 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $359 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $359 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain v ...
From $359 per night (USD)VRBO
- From $183 per night (USD)
Expedia
Your Perfect Blue Ridge Mountain Hideaway near 151
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About this space A six-figure tiny home in the epicenter of VA's Brew Ridge Trail. FORBES listed this model as the most ...
From $183 per night (USD)Expedia
- From $488 per night (USD)
VRBO
Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Drive up Fox Sparrow Lane through a tunnel of Blue Ridge trees, and the cabin appears between the pines. Inside: soaring ...
From $488 per night (USD)VRBO
- From $792 per night (USD)
Expedia
Little Bear: 4br/ 4ba, mountain & valley view. Pet friendly!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Little Bear! We'd love to provide you with a comfortable stay and clear views so you can enjoy the beauty of ...
From $792 per night (USD)Expedia
- From $331 per night (USD)
VRBO
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the heart of Wintergreen, This charming slope side 2-bedroom/ 2-bath. (sleeps six) condo steps from the ski ...
From $331 per night (USD)VRBO
- From $358 per night (USD)
Expedia
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Blackrock Escape! Our home is the perfect getaway for couples and small families. *Sleeps 4: Two King beds ...
From $358 per night (USD)Expedia
- From $267 per night (USD)
VRBO
Wintergreen Condo -Steps to Ski and restaurants
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the perfect blend of comfort and adventure at our Wintergreen Resort condo. Nestled amidst the pristine beauty ...
From $267 per night (USD)VRBO
- From $787 per night (USD)
Expedia
Mountain Mindset: Pup Friendly + Trail
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Downstairs Living Room: Smart TV, 2 couches, accent chairs (comfortable seating for 7-8). Sitting Room: 4 lounge chair ...
From $787 per night (USD)Expedia
- From $731 per night (USD)
VRBO
Eagles Court 24 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Eagles Court Classic Mountain Retreat Enjoy a classic Wintergreen mountain getaway in this inviting 3-bedroom, 2-bath c ...
From $731 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Three Ridges 84 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Three Ridges Mountain Escape Enjoy a relaxing retreat in this 1-bedroom, 1-bath condo in Three Ridges at Wintergreen Re ...
From $339 per night (USD)Expedia
- From $744 per night (USD)
VRBO
Shenandoah Ridge 07 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Shenandoah Ridge Spacious Mountain Retreat Make yourself at home in this spacious 4-bedroom, 4-bath condo at Shenandoah ...
From $744 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 68 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Loft Mountain Escape Enjoy a peaceful retreat in this comfortable loft-style guest room at the Mounta ...
From $297 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 54 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Pet-Friendly Loft Retreat Escape to the mountains in this cozy loft-style guest room at the Mountain Inn, ...
From $297 per night (USD)VRBO
- From $870 per night (USD)
Expedia
Shenandoah Ridge 01 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Shenandoah Ridge Spacious Five-Bedroom Retreat Escape to the mountains in this expansive 5-bedroom, 4½-bath condo at Sh ...
From $870 per night (USD)Expedia
- From $596 per night (USD)
VRBO
Northridge 09 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Northridge Spacious Mountain Getaway Make yourself at home in this spacious 3-bedroom, 3-bath condo in Northridge at Wi ...
From $596 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Overlook 04 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Overlook Mountain Retreat Enjoy a peaceful mountain escape in this 2-bedroom, 2-bath condo in Overlook at Wintergreen R ...
From $507 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 79 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Escape Make the most of your Wintergreen getaway in this inviting loft-style guest room at t ...
From $297 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 63 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Pet-Friendly King Loft Enjoy a relaxing mountain getaway in this inviting loft-style guest room at the Mou ...
From $297 per night (USD)Expedia
- From $744 per night (USD)
VRBO
Shenandoah Ridge 09 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Shenandoah Ridge Spacious Mountain Escape Enjoy a spacious mountain escape in this 4-bedroom, 4-bath condo at Shenandoa ...
From $744 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 52 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Cozy Loft Retreat Enjoy a charming mountain getaway in this cozy loft-style guest room at the Mountain Inn ...
From $297 per night (USD)Expedia
- From $829 per night (USD)
VRBO
Overlook 48 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Overlook Spacious Mountain Retreat Enjoy a spacious mountain escape in this inviting 4-bedroom, 4-bath condo at Overloo ...
From $829 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Cliffs 26 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cliffs Mountain Getaway Relax and enjoy the mountain setting in this 2-bedroom, 2-bath condo in Cliffs, located in Wint ...
From $507 per night (USD)Expedia
- From $507 per night (USD)
VRBO
Overlook 05 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Overlook Cozy Mountain Escape Escape to the mountains in this 2-bedroom, 2-bath condo in Overlook at Wintergreen Resort ...
From $507 per night (USD)VRBO
- From $504 per night (USD)
Expedia
Highlands 05 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Highlands Mountain Escape Escape to the mountains in this 2-bedroom, 2-bath condo in Highlands at Wintergreen Resort, n ...
From $504 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 78 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Retreat Settle into a peaceful mountain escape in this cozy loft-style guest room at the Mou ...
From $297 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 62 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Two-Double Loft Escape Plan a relaxing Wintergreen getaway in this charming loft-style guest room at the M ...
From $297 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 61 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Two-Queen Loft Retreat Make your next Wintergreen getaway comfortable and convenient in this loft-style gu ...
From $297 per night (USD)VRBO
- From $744 per night (USD)
Expedia
Trillium Place 01 with Wintergreen Advantage
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 8
Trillium Spacious Mountain Retreat Escape to the mountains in this spacious 4-bedroom, 3-bath condo at Trillium, locate ...
From $744 per night (USD)Expedia
- From $604 per night (USD)
VRBO
Stoneridge 69 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stoneridge Pet-Friendly Mountain Retreat Enjoy a memorable mountain getaway in this spacious 3-bedroom, 3-bath condo at ...
From $604 per night (USD)VRBO
- From $744 per night (USD)
Expedia
Shenandoah Ridge 16 with Wintergreen Advantage
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 8
Shenandoah Ridge Relaxing Mountain Retreat Experience a relaxing mountain getaway in this spacious 4-bedroom, 4-bath co ...
From $744 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 58 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Getaway Escape to the mountains in this comfortable loft-style guest room at the Mountain In ...
From $297 per night (USD)VRBO
- From $550 per night (USD)
Expedia
Fairway Woods 36 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fairway Woods Cozy Mountain Escape Unwind in the peaceful mountain setting of this 3-bedroom, 2-bath condo in Fairway W ...
From $550 per night (USD)Expedia
- From $870 per night (USD)
VRBO
Shenandoah Ridge 13 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Shenandoah Ridge Spacious Mountain Escape Make the most of your Wintergreen getaway in this spacious 5-bedroom, 4-bath ...
From $870 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Mountain Inn Lodge 55 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Double-Bed Loft Retreat Enjoy a relaxing stay in this inviting loft-style guest room at the Mountain Inn, ...
From $297 per night (USD)Expedia
- From $870 per night (USD)
VRBO
Stonewall Court 21 with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Stonewall Court Five-Bedroom Mountain Escape Settle into a spacious mountain retreat in this 5-bedroom, 4½-bath condo a ...
From $870 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Timbers Studio 08 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Escape Enjoy a comfortable mountain getaway in this inviting hotel-style guest room at the ...
From $270 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Timbers Studio 05 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Pet-Friendly King Retreat Enjoy a comfortable hotel-style guest room in the Timbers complex, conveniently locat ...
From $313 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Mountain Inn Studio 96 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Main-Floor King Getaway Settle into a welcoming hotel-style guest room on the main floor of the Mountain I ...
From $270 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Laurelwood 44 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Laurelwood Mountain Escape Escape to the mountains in this 1-bedroom, 1-bath condo in Laurelwood at Wintergreen Resort, ...
From $339 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Mountain Inn Studio 97 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Pet-Friendly King Retreat Enjoy a relaxing mountain getaway in this charming hotel-style guest room on the ...
From $270 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Timbers Studio 07 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Retreat Settle into a welcoming hotel-style guest room in the Timbers complex, convenientl ...
From $313 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Highlands 37 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Highlands Mountain Retreat Settle into a cozy 1-bedroom, 2-bath condo in Highlands, tucked away in Wintergreen's scenic ...
From $360 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Highridge Court 24 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Highridge Court Mountain Escape Enjoy a cozy retreat in this 1-bedroom, 2-bath condo in Highridge Court, nestled in Win ...
From $360 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Laurelwood 84 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Laurelwood Mountain Getaway Enjoy a cozy retreat in this 1-bedroom, 1-bath condo in Laurelwood at Wintergreen Resort, i ...
From $339 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Cliffs 21 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Cliffs Mountain RetreatCliffs Mountain Retreat Escape to the mountains in this 1-bedroom, 1-bath condo in Cliffs, locat ...
From $360 per night (USD)VRBO
- From $267 per night (USD)
Expedia
Timbers Studio 06 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Retreat Settle into a cozy hotel-style guest room in the Timbers buildings, conveniently l ...
From $267 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Three Ridges 91 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Three Ridges Cozy Mountain Retreat Make yourself at home in this 2-bedroom, 2-bath condo in the Three Ridges community ...
From $465 per night (USD)VRBO
- From $843 per night (USD)
Expedia
Nancy's Edelweiss with Wintergreen Advantage
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
This lovely 6-bedroom home is located on a quiet cul-de-sac and only minutes away from the Mountain Inn & main ski area. ...
From $843 per night (USD)Expedia
- From $747 per night (USD)
VRBO
Chestnut Springs with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This beautiful five bedroom home is conveniently located less than one mile from the Devil’s Knob Golf and Tennis Center ...
From $747 per night (USD)VRBO
- From $643 per night (USD)
Expedia
Bull City Bungalow with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our Bull City Bungalow! Bull City Bungalow is a fully renovated and tastefully decorated 4 bedroom, 3 ½ bath ...
From $643 per night (USD)Expedia
- From $510 per night (USD)
VRBO
Bear Necessities with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Start your adventure and step into Bear Necessities. A picturesque three-bedroom home in the rolling landscape of Winter ...
From $510 per night (USD)VRBO
- From $643 per night (USD)
Expedia
Blackrock Vista with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
4-Bedroom Home / Sleeps 8 Home Features • 3008 Square Feet • Complete modern kitchen with full-size refrigerator, stove, ...
From $643 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Timbers Studio 43 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Retreat Relax in a welcoming hotel-style guest room at the Timbers complex, ideally locate ...
From $313 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Timbers Studio 14 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Queen Bed Hotel-Style Retreat Make yourself comfortable in this inviting hotel-style guest room at the Timbers ...
From $270 per night (USD)Expedia
- From $642 per night (USD)
VRBO
Whispering Elm with Wintergreen Advantage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Whispering Elm is located at the top of the mountain in close proximity to fabulous hiking, skiing, the Devil’s Knob Gol ...
From $642 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Timbers Studio 18 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Hotel-Style Getaway Settle into a welcoming hotel-style guest room at the Timbers complex, ideally loc ...
From $270 per night (USD)Expedia
- From $746 per night (USD)
VRBO
Serendipity with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
With only 2 steps to access entry to the house, it is easily accessible for your convenience. A beautiful, large deck is ...
From $746 per night (USD)VRBO
- From $313 per night (USD)
Expedia
Timbers Studio 13 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
"Timbers King Bed Mountain Retreat Make yourself comfortable in this inviting hotel-style guest room at the Timbers com ...
From $313 per night (USD)Expedia
- From $267 per night (USD)
VRBO
Timbers Studio 38 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers Pet-Friendly King Retreat Escape to a welcoming hotel-style guest room at the Timbers complex, ideally situated ...
From $267 per night (USD)VRBO
- From $504 per night (USD)
Expedia
Whispering Pines with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the fresh mountain air and picturesque forested surroundings when you stay at Whispering Pines, a secluded 3-bedro ...
From $504 per night (USD)Expedia
- From $746 per night (USD)
VRBO
Orchard House with Wintergreen Advantage
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
A Beautifully Appointed Mountain Retreat at Wintergreen Orchard House is a distinctive five-bedroom, six-and-a-half-bath ...
From $746 per night (USD)VRBO
- From $504 per night (USD)
Expedia
Black Dog Treehouse with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Do you hear that? The mountains are calling, and this is your perfect home away from home. The Black Dog Treehouse is a ...
From $504 per night (USD)Expedia




































































































