
Nelson Area Rentals
- From $217 per night (USD)
VRBO
Unique Stay! Yurt with Mountain View, 1 min to Breweries & Hiking, 5 min to Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Come for a memorable stay at the Rockfish Valley Yurt and enjoy "glamping" at its finest! Picturesque mountain views a ...
From $217 per night (USD)VRBO
- From $256 per night (USD)
Expedia
Cozy dog- friendly condo that sleeps 6 -with pools and VIEWS, minutes to slopes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a tranquil 2-bedroom condo at Wintergreen Resort! This well appointed property offers a perfect place for unw ...
From $256 per night (USD)Expedia
- From $409 per night (USD)
VRBO
Mtn Views~Fire Pit~King Bed~Lake~Breweries 1 mi!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About this space The Blue Ridge Cabin is on the 151 Brew-ridge Trail at the base of the mountain, mins to wineries, brew ...
From $409 per night (USD)VRBO
- From $348 per night (USD)
VRBO
Spacious home for relaxation in Roseland. 30 min from hiking trails, wineries.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Stay peacefully in Roseland at this 4-bedroom farmhouse on a working cattle and sheep farm. With a full dining room and ...
From $348 per night (USD)VRBO
- From $444 per night (USD)
VRBO
Overlook 180 degree views w/Peloton!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy some of the best views at Wintergreen from this updated Overlook condo. Take in beautiful sunrises from the privat ...
From $444 per night (USD)VRBO
- From $240 per night (USD)
Expedia
Altitude Adjustment-It's Pumpkin Spice Time!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This is a newly renovated condo with new flooring and furniture . Great place to come and relax after a day of hiking, ...
From $240 per night (USD)Expedia
- From $456 per night (USD)
VRBO
Slopes @ Tyro
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
We have a spacious, slope side, 3 level home with a convenient ski out basement. The resort & its surrounding areas offe ...
From $456 per night (USD)VRBO
- From $674 per night (USD)
Expedia
Our Mountain Getaway
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Come make Our Mountain Getaway your own! This is a very private home surrounded by beautiful mountain views with lots of ...
From $674 per night (USD)Expedia
- From $494 per night (USD)
VRBO
Cliffs Edge-A Contemporary Mountain Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredi ...
From $494 per night (USD)VRBO
- From $299 per night (USD)
Expedia
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this cozy condo in Wintergreen Resort. The sunrises are spectacular and the views glorious! This charming prop ...
From $299 per night (USD)Expedia
- From $427 per night (USD)
VRBO
Privacy and Views in Wintergreen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to our cozy Wintergreen home, located on one of the most private lots in the area. You'll truly feel at peace wi ...
From $427 per night (USD)VRBO
- From $743 per night (USD)
Expedia
Branch and Barrel: Hot Tub & Sauna + Mtn Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Branch and Barrel, the perfect quiet getaway right off the Nelson 151 Brew Trail. This stunning 1891 farmh ...
From $743 per night (USD)Expedia
- From $88 per night (USD)
VRBO
Experience the Magic at our Luxury 2 Bdrm, w/Majestic Blue Ridge Mountain Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
TERRIFIC place for Traveling Health Care Professionals, Relocating Professionals, Digital Nomads, Short term Contractors ...
From $88 per night (USD)VRBO
- From $658 per night (USD)
VRBO
The Moose Lodge-Hot Tub/Game Room/Fire Pit/Grill/Walk to Slopes-0.7mi to Lodge
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Welcome to The Moose Lodge at Wintergreen – Your Mountain Escape Awaits! Gather your family and friends and make unforg ...
From $658 per night (USD)VRBO
- From $363 per night (USD)
VRBO
WTG Luxe Cliff House Retreat: Hike, Sip, Relax
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the perfect getaway at Boho Cliff House, a stunning 3BR, 2BA home nestled in the heart of Wintergreen Resort. I ...
From $363 per night (USD)VRBO
- From $211 per night (USD)
Expedia
Blue Ridge Montebello Cabin 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the beauty of Montebello from this cozy 1-bedroom cabin. The bedroom features a comfortable queen bed, perfect ...
From $211 per night (USD)Expedia
- From $609 per night (USD)
VRBO
Escape to a modern A-frame retreat with mountain views, a hot tub, cozy cinema lounge, and easy access to Nelson 151, Shenandoah National Park, hiking trails, wineries, and breweries.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Peak Retreat, a luxury A-frame perched high above the Blue Ridge Mountains with sweeping panoramic views and a ...
From $609 per night (USD)VRBO
- From $227 per night (USD)
Expedia
Blue Ridge Montebello Cabin 2
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Consider this charming cabin your home away from home while you visit Montebello. With 2 cozy bedrooms featuring a king ...
From $227 per night (USD)Expedia
- From $286 per night (USD)
VRBO
Pool Access: Scenic Condo in Wintergreen Resort!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Year-Round Mountain Retreat | Seasonal Shuttle to Lift | Blue Ridge Backdrop Mornings come with a view at this Wintergr ...
From $286 per night (USD)VRBO
- From $1043 per night (USD)
Expedia
Wintergreen 5BR with Hot Tub, Sauna, Firepit
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Marigold on the Mountain! Located in the heart of Wintergreen, Marigold features a hot tub and cedar barrel s ...
From $1043 per night (USD)Expedia
- From $1132 per night (USD)
VRBO
Mountain Views, Hot Tub, Impeccable Design
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Chasing Altitudes, a designer-decorated Wintergreen home with fantastic year-round views. The multiple decks ...
From $1132 per night (USD)VRBO
- From $1473 per night (USD)
Expedia
Modern Luxe House Hot Tub 20ppl
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 20
Escape to this luxurious 7BR/6.5BA farmhouse retreat, perfectly nestled in the heart of the Blue Ridge Mountains. With s ...
From $1473 per night (USD)Expedia
- From $273 per night (USD)
VRBO
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wake up to the fresh mountain air in a condo on the edge of the mountain. The most breathtaking sunrises and views of th ...
From $273 per night (USD)VRBO
- From $321 per night (USD)
VRBO
Charming 2-bedroom condo in beautiful Wintergreen Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Your family will be close to everything when you stay at this centrally-located retreat. Nestled in the sought after Wi ...
From $321 per night (USD)VRBO
- From $252 per night (USD)
VRBO
Willow Haven: Cozy cabin in delightful Afton
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Consider this cabin your home away from home while you visit Afton. Nestled in the heart of this enchanting city, our we ...
From $252 per night (USD)VRBO
- From $621 per night (USD)
Expedia
Faber Farmhouse: Hot Tub Near & Wineries/Breweries
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
🛌 Sleeps 9 | 💦 NEW Hot Tub | 🍷🍺 Central to Wineries & Breweries Below is a breakdown of the 3-story, newly-renovate ...
From $621 per night (USD)Expedia
- From $231 per night (USD)
VRBO
Prime WTG Location - Summer Fun at Swoopside Hideaway - Outdoor Pools
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stay at the heart of Wintergreen Resort at Swoopside Hideaway, a wonderful 2BR, 1.5BA condo perched right on the Eagles ...
From $231 per night (USD)VRBO
- From $574 per night (USD)
VRBO
Foxwood at Stoney Creek • Wintergreen + Wine Trail Base • Mtn Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Spacious 4BR/3BA home in Stoney Creek at Wintergreen on 1.4 peaceful acres. Enjoy a screened-in porch with skylights and ...
From $574 per night (USD)VRBO
- From $394 per night (USD)
VRBO
Mountain Views in Wintergreen
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Dogwood Retreat! This spacious Wintergreen home features two levels of decks. On the upper deck, you'll love ...
From $394 per night (USD)VRBO
- From $169 per night (USD)
Expedia
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your cozy getaway awaits in Afton at this marvelous cottage. With 1 queen bed, WiFi, heating, and a hair dryer, guests w ...
From $169 per night (USD)Expedia
- From $392 per night (USD)
VRBO
Wintergreen Mountain Top Escape: Steps to Golf, Hiking & High-Country Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
• Things to know (we want you to relax, not waste your time!) • 4 bedrooms (sleeps 10) • 3 Full baths • No pets • Yes, v ...
From $392 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Highridge 06 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Highridge Mountain Getaway Enjoy a relaxing mountain escape in this 2-bedroom, 2-bath condo in the Highridge community ...
From $507 per night (USD)Expedia
- From $1090 per night (USD)
VRBO
Family-friendly 10-bedroom B&B near Wintergreen golf & ski. Great for groups!
- Bedrooms:
- 3
- Bathrooms:
- 10
- Sleeps:
- 24
Located 30 miles south of Charlottesville, VA, Acorn Inn is a convenient rendezvous spot between northern and southern s ...
From $1090 per night (USD)VRBO
- From $799 per night (USD)
Expedia
Wintergreen Luxury, Breathtaking Views
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Stargazer, one of Wintergreen's premier properties. The views are second-to-none throughout the home, and esp ...
From $799 per night (USD)Expedia
- From $457 per night (USD)
VRBO
Secluded Mountain Cabin Firepit 12ppl
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
In the heart of Fortune’s Cove, surrounded by 800 acres of hiking trails, this secluded mountain home offers the perfect ...
From $457 per night (USD)VRBO
- From $336 per night (USD)
Expedia
Timbers Lodge 31 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
First floor slope side unit with walkout ski in and ski out access. Located in the Timbers complex near the Blackrock Vi ...
From $336 per night (USD)Expedia
- From $297 per night (USD)
VRBO
Mountain Inn Lodge 77 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn King Bed Loft Retreat Make your Wintergreen stay comfortable and convenient in this cozy loft-style guest ...
From $297 per night (USD)VRBO
- From $1308 per night (USD)
VRBO
Oh Deer NEW LUXURY-renovated, hot tub/sauna, views
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 18
OH DEER! Welcome to your perfect escape in the Blue Ridge Mountains! Nestled just steps from the slopes of Wintergreen ...
From $1308 per night (USD)VRBO
- From $973 per night (USD)
VRBO
Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Welcome to The Wintergreen Cozy! Reconnect and unwind in this 5-bed, 3-bath mountain retreat, perfect for large/multipl ...
From $973 per night (USD)VRBO
- From $267 per night (USD)
Expedia
Timbers Studio 48 With Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers King Bed Mountain Retreat Make yourself at home in this inviting hotel-style guest room at the Timbers complex, ...
From $267 per night (USD)Expedia
- From $738 per night (USD)
VRBO
NEW Warren’s Woods! Lovely 5BD, 3BA Wintergreen home. Hot Tub! NEW SPRING RATES!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Wintergreen Resort is waiting for you at this 5-bedroom house. Each room offers an unique sleeping experience, from a ki ...
From $738 per night (USD)VRBO
- From $440 per night (USD)
VRBO
Brand new 3-bedroom house at the base of the Blue Ridge Mountains
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bucolic and chic— Take in all Nelson County’s Rockfish River Valley and “Brew Ridge Trail” (Rt. 151) have to offer in th ...
From $440 per night (USD)VRBO
- From $731 per night (USD)
VRBO
Dobie 36 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dobie Cozy Mountain Escape Enjoy a memorable mountain getaway in this inviting 3-bedroom, 3-bath condo at Dobie, conven ...
From $731 per night (USD)VRBO
- From $731 per night (USD)
Expedia
Dobie 48 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dobie Spacious Mountain Retreat Escape to Wintergreen in this spacious 3-bedroom, 3-bath condo at Dobie, ideally locate ...
From $731 per night (USD)Expedia
- From $343 per night (USD)
VRBO
Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to this cozy four-season mountain retreat tucked away on a private wooded lot in the heart of Wintergreen Resort. ...
From $343 per night (USD)VRBO
- From $520 per night (USD)
Expedia
Mntn View Hot Tub Foosball Fireplace Multi-Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
4min drive to Wintergreen skiing. Adventure and relaxation await at this mountain top Wintergreen Resort home! With 4 be ...
From $520 per night (USD)Expedia
- From $2082 per night (USD)
VRBO
Dragon's Back, 9BR 10BA in Wintergreen
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 18
Welcome to Dragon’s Back, one of Virginia's premier mountain chalets. With 6200 sq ft and some of the best views in the ...
From $2082 per night (USD)VRBO
- From $1259 per night (USD)
Expedia
Luxe Wellness+Family Fun • Hot Tub|Massage Chair|Sauna|3 Game Rooms|Heated Patio
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Escape to Chateau Greenstone, the Wintergreen retreat where wellness & family fun shine. Something for EVERYONE: Adults ...
From $1259 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Timbers 11 With Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Timbers One-Bedroom King Condo Enjoy a relaxing mountain retreat in this inviting one-bedroom condo at the Timbers, con ...
From $354 per night (USD)VRBO
- From $465 per night (USD)
Expedia
Three Ridges 05 With Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Three Ridges Ski-Access Retreat Enjoy a comfortable mountain getaway in this 2-bedroom, 2-bath condo in the Three Ridge ...
From $465 per night (USD)Expedia
- From $420 per night (USD)
VRBO
Lofty Pursuits: Spectacular View + EV Charger
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Loft Pursuits! This cliff-hanging cabin amidst arboreal oasis featuring deck with view of Three Ridges. Unwin ...
From $420 per night (USD)VRBO
- From $310 per night (USD)
Expedia
Three Little Bears: Walk to Ski & Swim
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FIRST FLOOR: LIVING ROOM - NEW sectional sofa, smart TV, wood-burning fireplace (firewood provided), board gams and ki ...
From $310 per night (USD)Expedia
- From $467 per night (USD)
VRBO
New Build! Log Cabin with Hot Tub in Wintergreen
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
Welcome to Loggin' Off, a log cabin built in 2024 in the heart of Wintergreen. This 6 bedroom home sleeps 15 and feature ...
From $467 per night (USD)VRBO
- From $317 per night (USD)
VRBO
Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Bring the whole family or your friends to this cozy cabin with lots of room for fun and relaxation. Check out the local ...
From $317 per night (USD)VRBO
- From $168 per night (USD)
VRBO
Luxury 1-BR Suite near Nelson 151 | Pet-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience upscale comfort in this 1-bedroom retreat featuring a king bed, queen sleeper sofa, full kitchen, and private ...
From $168 per night (USD)VRBO
- From $168 per night (USD)
Expedia
Pet-Friendly King Suite w/ Desk & Smart Entry
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience laid-back comfort in this inviting 1-bedroom suite featuring a king bed, queen sleeper sofa, and an in-suite ...
From $168 per night (USD)Expedia
- From $505 per night (USD)
VRBO
Amazing Mountain Views, Hot Tub and Close to Wineries and Breweries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Sit back, relax, and soak in the views. The Rockfish Retreat is nestled in the foothills of the Blue Ridge Mountains, ri ...
From $505 per night (USD)VRBO
- From $216 per night (USD)
Expedia
Wintergreen Condo w/ Pool: Near Hike & Market!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Walk to Wintergreen Conference Center | Near Hiking Trails | Community Pool Access Experience the best of the mountains ...
From $216 per night (USD)Expedia
- From $604 per night (USD)
VRBO
Three Ridges 27 With Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Three Ridges Charming Mountain Escape Make yourself at home in this charming 3-bedroom, 2-bath condo at Three Ridges, i ...
From $604 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Three Ridges 64 With Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Three Ridges Mountain Getaway Escape to the mountains in this 1-bedroom, 1-bath condo in Three Ridges at Wintergreen Re ...
From $339 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Treetop Mountain Escape - Fireplace, Views & Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wake up above the treetops in this beautifully updated top-floor condo at Wintergreen Resort — Virginia’s premier four-s ...
From $225 per night (USD)VRBO
- From $643 per night (USD)
Expedia
Antlers Aweigh with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Antlers Aweigh is located above a Wintergreen hiking trail, making this home a great launch pad for all your mountain ad ...
From $643 per night (USD)Expedia
- From $462 per night (USD)
VRBO
Serenity Cabin-Woodland Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Serenity Cabin: Your Perfect Woodland Retreat Nestled among the trees, this recently renovated timber-framed ...
From $462 per night (USD)VRBO
- From $339 per night (USD)
Expedia
Northridge 07 With Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Retreat in Northridge Escape to the mountains in this 1-bedroom, 2-bath condo in Northridge, located in Winter ...
From $339 per night (USD)Expedia
- From $731 per night (USD)
VRBO
Dobie 24 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dobie Spacious Mountain Getaway Experience a relaxing Wintergreen getaway in this spacious 3-bedroom, 3-bath condo at D ...
From $731 per night (USD)VRBO
- From $676 per night (USD)
Expedia
Almost Heaven
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Welcome to 'Almost Heaven"! A cozy, A-frame in the heart of Wintergreen Resort. This 3-bedroom, 3-bath retrea ...
From $676 per night (USD)Expedia
- From $555 per night (USD)
VRBO
Trail Magic- Sk-in & Ski-out
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Trail Magic | Ski-In/Ski-Out Lodge at Wintergreen Resort with Hot Tub Experience the magic of the mountain ...
From $555 per night (USD)VRBO
- From $239 per night (USD)
VRBO
All Downhill From Here
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Enjoy everything you need atop Virginia's <strong>Wintergreen Resort</strong>. This newly renovated condominium is lo ...
From $239 per night (USD)VRBO
- From $667 per night (USD)
VRBO
Highlands 24 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Highlands Spacious Mountain Retreat Escape to the peaceful mountain setting of this spacious 3-bedroom, 3-bath condo in ...
From $667 per night (USD)VRBO
- From $338 per night (USD)
Expedia
Gum Tree #1 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Relaxing Mountain Escape at Wintergreen Resort Enjoy a peaceful getaway in this 1-bedroom, 1-bath condo at Wintergreen ...
From $338 per night (USD)Expedia
- From $1204 per night (USD)
VRBO
Wintergreen Luxury, Best Views in VA!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Welcome to Blackrock Manor, a one-of-a-kind luxury chalet in Wintergreen that sleeps 16. Experience spectacular mountain ...
From $1204 per night (USD)VRBO
- From $507 per night (USD)
Expedia
Ledges 66 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ledges Mountain Getaway Make yourself at home in this 2-bedroom, 2-bath condo in Ledges, nestled in Wintergreen's sceni ...
From $507 per night (USD)Expedia
- From $359 per night (USD)
VRBO
Vistas 87 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Vistas Cozy Mountain Escape Enjoy a peaceful getaway in this 1-bedroom, 2-bath condo in Vistas, nestled in Wintergreen' ...
From $359 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Vistas 75 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Vistas Mountain Retreat Escape to the mountains in this 1-bedroom, 2-bath condo in Vistas, located in Wintergreen's sce ...
From $360 per night (USD)Expedia
- From $501 per night (USD)
VRBO
Overlook 08 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Overlook Mountain Getaway Unwind in this 2-bedroom, 2-bath condo in Overlook at Wintergreen Resort, nestled in the scen ...
From $501 per night (USD)VRBO
- From $838 per night (USD)
VRBO
Spacious 3BR 3BA Pet Friendly Resort Condo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Escape to our spacious 3-bed, 3-bath mountain condo, perfect for families or groups. Enjoy cozy evenings by the gas fire ...
From $838 per night (USD)VRBO
- From $507 per night (USD)
VRBO
Ledges 78 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ledges Valley View Retreat Take in beautiful valley views from this top-floor, end-unit condo in Ledges at Wintergreen ...
From $507 per night (USD)VRBO
- From $465 per night (USD)
Expedia
Tanners Ridge 21 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tanners Ridge Mountain Escape Enjoy a relaxing retreat in this 2-bedroom, 2-bath condo in Tanners Ridge, located in Win ...
From $465 per night (USD)Expedia
- From $507 per night (USD)
VRBO
Overlook 29 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Overlook Scenic Mountain Retreat Take in the beauty of Wintergreen from this 2-bedroom, 2-bath condo in the Overlook co ...
From $507 per night (USD)VRBO
- From $667 per night (USD)
Expedia
Ledges 72 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Ledges Spacious Mountain Escape Enjoy a relaxing Wintergreen getaway in this spacious 3-bedroom, 3-bath condo at Ledges ...
From $667 per night (USD)Expedia
- From $667 per night (USD)
VRBO
Ledges 52 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Ledges Peaceful Mountain Retreat Escape to a peaceful mountain getaway in this spacious 3-bedroom, 3-bath condo at Ledg ...
From $667 per night (USD)VRBO
- From $465 per night (USD)
Expedia
Laurelwood 48 with Wintergreen Advantage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Laurelwood Mountain Escape Escape to the mountains in this inviting 2-bedroom, 2-bath retreat in Laurelwood at Wintergr ...
From $465 per night (USD)Expedia
- From $604 per night (USD)
VRBO
Northridge 06 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Northridge Tranquil Mountain Retreat Escape to the tranquility of Wintergreen Resort in this spacious 3-bedroom, 3-bath ...
From $604 per night (USD)VRBO
- From $604 per night (USD)
Expedia
Stoneridge 81 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stoneridge Cozy Mountain Escape Enjoy a relaxing mountain getaway in this spacious 3-bedroom, 3-bath condo at Stoneridg ...
From $604 per night (USD)Expedia
- From $604 per night (USD)
VRBO
Stoneridge 70 with Wintergreen Advantage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stoneridge Spacious Mountain Retreat Settle into a spacious mountain getaway in this 3-bedroom, 3-bath condo at Stoneri ...
From $604 per night (USD)VRBO
- From $467 per night (USD)
Expedia
Little Haven Cottage: Walk to Meade Tasting
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to the serenity of the Blue Ridge Mountains with a stay at our cozy, well-appointed cottage located directly on t ...
From $467 per night (USD)Expedia
- From $341 per night (USD)
VRBO
Cool Mountain Breezes on The Slopes- It's Pumpkin Spice Time!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Your Wintergreen Resort adventure begins at this marvelous 3-bedroom home with a 2-levels of decks. With 2 king beds, 2 ...
From $341 per night (USD)VRBO
- From $284 per night (USD)
Expedia
Mountain Inn Studio 93 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mountain Inn Main-Floor King Retreat Enjoy a stylish and comfortable stay in this hotel-style guest room on the main fl ...
From $284 per night (USD)Expedia
- From $527 per night (USD)
VRBO
4 Bedroom mountain cabin in the relaxing Wintergreen Resort with AC & Fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Heaven on 11 is a comfortable 4 BR / 3 BA house with 3 Queen Beds, and a Twin trundle bed, sleeps 8, with two bedrooms o ...
From $527 per night (USD)VRBO
- From $419 per night (USD)
Expedia
Newly Built Designer Home in Wintergreen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Welcome to Onyx Hill, a custom built 4-bedroom, 3.5-bathroom home nestled within the picturesque Wintergreen Resort! Eve ...
From $419 per night (USD)Expedia
- From $646 per night (USD)
VRBO
The Snow House New Hot Tub Pet Friendly Creek PacMan
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 13
Hot Tub Coming Dec. 2025*** We added a beautiful 8 seater hot tub for our deck overlooking the serene deck and creek be ...
From $646 per night (USD)VRBO
- From $1028 per night (USD)
Expedia
Fully Loaded 8BR in Wintergreen! Sleeps 23
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 23
Welcome to Crawfords Escape, a designer-decorated 8BR 4500 sf chalet in scenic Wintergreen that sleeps 23. Outside, enjo ...
From $1028 per night (USD)Expedia
- From $526 per night (USD)
VRBO
Newly Remodeled 4BR/4.5BA Golf Front Townhome. Pet Friendly!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Completely Remodeled Golf Front Townhome | Walk to Ski Shuttle Stop, Spa & Fitness Center | Pet-Friendly Experience the ...
From $526 per night (USD)VRBO
- From $472 per night (USD)
Expedia
The Honey Den - Your Family's Summer Retreat - Outdoor Pools, Nature, Adventure
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
Welcome to The Honey Den - a warm 5BR, 4.5BA mountain home designed for slow mornings, golden-hour decks, and easy toget ...
From $472 per night (USD)Expedia
- From $506 per night (USD)
VRBO
Escape to Wintergreen Resort! Our pet & kid-friendly 2BR/2BA townhome is steps from skiing, dining & the Market. Hike, ski, swim, or sip at nearby wineries & breweries—adventure awaits year-round!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wintergreen Resort is a fantastic, all season destination, with adventures for everyone! We are a pet and kid friendly, ...
From $506 per night (USD)VRBO
- From $405 per night (USD)
VRBO
Family-favorite rental nestled in the woods at the top of the Wintergreen Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
The Blue Ridge Mountains are calling you to this 3-level, 4 bed/3 bath home for an epic getaway! A family-favorite renta ...
From $405 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Ledges 50 with Wintergreen Advantage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ledges Mountain Escape Enjoy a peaceful retreat in this 1-bedroom, 1-bath condo in Ledges, nestled in Wintergreen's sce ...
From $360 per night (USD)VRBO
- From $374 per night (USD)
Expedia
Incredible Cabin with Beautiful Indoor and Outdoor Living Spaces in Virginia
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to your perfect escape at this incredible resort in VA! Just 3 minutes from the ski slopes and snow tubing, our ...
From $374 per night (USD)Expedia
- From $594 per night (USD)
VRBO
Summer Golf - Walk to Ski | Sleeps 12 | Pets OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
✨ Luxury Wintergreen Retreat | Stoney Creek Golf Access | Ski, Golf, Pet-Friendly | Sleeps 12 Escape to the mountains a ...
From $594 per night (USD)VRBO
- From $650 per night (USD)
Expedia
Charming Cabin Rental near Wineries and Hiking Trails in Afton, Virginia
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our home away from home in the rolling hills of Afton, VA! We love to experience new restaurants, wineries, b ...
From $650 per night (USD)Expedia




































































































