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From $250 per night (USD)
VRBO
Hanging Rock Cabin -
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Part of Love Ridge Mountain Lodging. Named for a popular nearby hiking and mountain biking trail. Completely renovated c ...
From $250 per night (USD)
VRBO
From $326 per night (USD)
Expedia
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Rosie's Retreat (FKA: Ro's Retreat) Come enjoy this cozy 3 bedroom/3 bath condo located on the 18th hole of Devils Knob. ...
From $326 per night (USD)
Expedia
From $422 per night (USD)
VRBO
Coastal Farmhouse Getaway!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Take it easy at this unique and tranquil getaway. This fully renovated historic farmhouse sits on 4 acres on Windmill Po ...
From $422 per night (USD)
VRBO
From $138 per night (USD)
Expedia
Nona's Cottage-Waynesboro/Shenandoah Valley, VA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Centrally located to hiking and sight seeing in the Blue Ridge Mountains and Skyline Drive. Within minutes of wineries, ...
From $138 per night (USD)
Expedia
From $150 per night (USD)
VRBO
Queen City Twin of Staunton VA
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
This Staunton, VA Twin Unit has a distinct vibe and mid century modern feel. Located just 1 mile to Gypsy Hill Park and ...
From $150 per night (USD)
VRBO
From $152 per night (USD)
Expedia
Queen City Twin 2 of Staunton VA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This Staunton, VA Twin 2 Unit has a modern, but warm feel. Located just 1 mile to Gypsy Hill Park and less than 2 miles ...
From $152 per night (USD)
Expedia
From $179 per night (USD)
VRBO
Ready for Ski Season! Book NOW!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Great location! This 1 bedroom, 1 bathroom condo is on the mountain within Wintergreen Resort. Wintergreen Natu ...
From $179 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Hilltop Escape >1 mile from North River Close to North River, Hone Quarry
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hilltop Escape Situated on 7.5 acres, Close to North River, Bridgewater College, Hone Quarry This beautifully appointed ...
From $292 per night (USD)
Expedia
From $122 per night (USD)
VRBO
Downtown Waynesboro, Close to 151, Blue Ridge Parkway, Close to Augusta Health and UVA
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy this cozy abode, ideal for singles or a couple looking for an affordable and convenient spot to enjoy the sites! ...
From $122 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
Bedrooms:
2
Bathrooms:
4
Sleeps:
5
Enjoy your getaway in a peaceful setting in this unique cabin built in 1840 with built addition, walk-around porch and d ...
From $235 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Smoky Bear Cabin
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious 3 BR/2BA cabin, located a walk away from the ski slopes. Ski all day and relax at night by the jacuzzi hot tub ...
From $220 per night (USD)
VRBO
From $453 per night (USD)
VRBO
Stunning Wintergreen Resort Home: Ski & Golf!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Prepare to make lifelong memories on the mountain when staying at this beautiful Wintergreen Resort vacation rental! Whe ...
From $453 per night (USD)
VRBO
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VRBO
3 Bedroom Condo
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Cozy three bedroom condo located in Three Ridges. Two minute walk to slopes and the resort lodge and restaurants. Perfe ...
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VRBO
From $369 per night (USD)
Expedia
Life is better at the Cabin
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This stunning log cabin style home is the ultimate exclusive getaway to nature, relaxation, and fun for you and your lov ...
From $369 per night (USD)
Expedia
From $670 per night (USD)
VRBO
Horizen House
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
HoriZEN House - Beautiful Mountain Home! HoriZEN house is the perfect place to relax, unwind and find your inner zen. ...
From $670 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Peacefield: Farmhouse in the Shenandoah Valley
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
NEW LISTING. Hosted by Amos and Carol, this entire handcrafted & beautifully updated home welcomes families & travelers ...
From $329 per night (USD)
Expedia
From $384 per night (USD)
VRBO
Dogs OK Pool Tennis Grill Pack 'n Play Golf Hiking
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Circle-up around the firepit on the back deck under the star-lit sky, or cozy up on the comfy sofa around the indoor fir ...
From $384 per night (USD)
VRBO
From $557 per night (USD)
Expedia
Modern Wintergreen Cabin with Hot Tub, Sauna
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Welcome to Blue Ridge Hollow! This designer-decorated cabin in the heart of Wintergreen has one of the best outdoor spac ...
From $557 per night (USD)
Expedia
From $105 per night (USD)
VRBO
Mid-Century Downtown Staunton Loft
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
When 3 is a crowd, try a romantic hideaway for 2. Just uphill from the downtown restaurants. A mid-century loft in a 19 ...
From $105 per night (USD)
VRBO
From $343 per night (USD)
Expedia
Leaf-Peeping at Oak Ledge! Trails+Tastings+Peace
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover our peaceful retreat at Oak Ledge, a charming 3BR, 2.5BA cabin just steps from Wintergreen Resort! Newly renova ...
From $343 per night (USD)
Expedia
From $758 per night (USD)
VRBO
4 BD Modern Design | Golf Course View | Arcade
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to the Castor Cabin - an impeccably decorated home in the heart of Wintergreen! This recently renovated space an ...
From $758 per night (USD)
VRBO
From $1595 per night (USD)
Expedia
Insane Mountain Views - New Listing
Bedrooms:
9
Bathrooms:
7
Sleeps:
18
One of the largest homes in Wintergreen with 7 bedrooms and 10 bathrooms. The floor-to-ceiling windows offer a sunrise ...
From $1595 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Beautiful 4-season Mountain Home- New Listing
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
You’ll be ideally positioned a minute walk away from the Highlands Ski Lift and Wintergreen Spa. The back deck has a gre ...
From $378 per night (USD)
VRBO
From $564 per night (USD)
VRBO
Private Blue Ridge Mountain Retreat/ Modern home immersed in natural beauty!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Peaceful, private retreat nestled in the beauty of the Blue Ridge Mountains. Unplug from the intrusions of modern life, ...
From $564 per night (USD)
VRBO
From $226 per night (USD)
VRBO
Wintergreen Resort Vacation Rental w/ Pool Access!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
No matter the season, you’ll have easy access to endless outdoor adventures when you stay at this cozy Wintergreen Resor ...
From $226 per night (USD)
VRBO
From $152 per night (USD)
Expedia
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Pet-Friendly One Bedroom Condo on a Scenic Golf Course Indulge in relaxation at this tranquil Wintergreen haven. No mat ...
From $152 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Open floor plan close to skiing, hiking, and dining.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Situated on Devil's Knob golf course, close to restaurants, hiking, skiing, and tubing, you'll find there's plenty to do ...
From $290 per night (USD)
VRBO
From $247 per night (USD)
Expedia
The red house
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This newly renovated(June 2023,) four bedroom two bath home is a five minute walk to historical downtown Staunton. On Sa ...
From $247 per night (USD)
Expedia
From $648 per night (USD)
VRBO
Serene Wintergreen Retreat, Nestled in the Trees
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to our cozy Wintergreen cabin in the trees! You'll truly feel at peace with nature on the three levels of decks ...
From $648 per night (USD)
VRBO
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Expedia
Valley Extended Suites - Executive Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Valley Extended Suites is surrounded by several beautiful areas to discover and explore within the Shenandoah Valley. We ...
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Expedia
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VRBO
Valley Extended Suites - Standard Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Valley Extended Suites is surrounded by several beautiful areas to discover and explore within the Shenandoah Valley. We ...
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VRBO
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Expedia
Valley Extended Suites - Studio Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Valley Extended Suites is surrounded by several beautiful areas to discover and explore within the Shenandoah Valley. We ...
Click For Pricing
Expedia
From $401 per night (USD)
VRBO
Entire Mid-Century Modern Farmhouse-Style Cottage hosted by Heather
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Charming 3BR Farmhouse Near Wineries & Blue Ridge Tunnel Freshly updated with farmhouse charm, The Little Farmhouse is a ...
From $401 per night (USD)
VRBO
From $746 per night (USD)
Expedia
Inviting Wine Cottage Hosted By Heather
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Spacious 5BR Wine Country Retreat w/ Fire Pit & Views Clean and full of mid-century charm, The Wine Cottage is a 5BR/3BA ...
From $746 per night (USD)
Expedia
From $418 per night (USD)
VRBO
Walk Downtown~Game Room~Gym~Fire Pit~Hammock!
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Step back in time at this centrally-located historic home! Walk to downtown restaurants, Wayne Theater & River Trail fro ...
From $418 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Clean and cozy loft! Right at Mountain Inn!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Cozy Mountain Inn loft with tree-top views. Close to everything with easy access to shops, restaurants and events. Perfe ...
From $193 per night (USD)
Expedia
From $591 per night (USD)
VRBO
Upscale and Family-Friendly in Wintergreen
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Welcome to Sutton's Roost, a designer-decorated home in the heart of Wintergreen. A perfect spot for groups or families, ...
From $591 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Fox'em Falls
Bedrooms:
0
Bathrooms:
0
Sleeps:
0
About this space Fox'em Falls is ready to host your group with 3 bedrooms, 2 full baths, a kitchen, dining area, cozy fa ...
From $301 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Ski-in/out Birds Eye View Fireplace DogOK King Bed
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Spend your days hiking the area’s 30+ miles of trails, completing the ninja warrior course, soaring down a zip line at ~ ...
From $330 per night (USD)
VRBO
From $330 per night (USD)
Expedia
North Central Loft: Sauna + Walk Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
FIRST FLOOR: ENTRY WAY - Daybed, nightstand with lamp, cubical storage SECOND FLOOR: LIVING ROOM - Couch, arm chairs ...
From $330 per night (USD)
Expedia
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VRBO
Elson's Overlook
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
About this space Stunning mountain views await you at this peaceful retreat. We welcome you to Elson's Overlook where yo ...
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VRBO
From $298 per night (USD)
Expedia
Luxury Condo in the Sky! Finest in Wintergreen!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just ...
From $298 per night (USD)
Expedia
From $651 per night (USD)
VRBO
Stunning Views, Hot Tub, Impeccable Design
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to Ryder's Ridge, a designer-decorated home on a quiet street in Wintergreen with amazing mountain views! Watch ...
From $651 per night (USD)
VRBO
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Expedia
Explore & Relax in Wintergreen!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Create family memories year round at this bright & open condo! Hit the spa next door, play a round of golf, hike down th ...
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Expedia
From $263 per night (USD)
VRBO
Farmhouse at the foot of the Blue Ridge Mountains
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Updated, pet-friendly farmhouse with extra-large fenced in yard, located in Waynesboro - 10 minutes from Skyline Drive ...
From $263 per night (USD)
VRBO
From $222 per night (USD)
VRBO
Wintergreen Resort Vacation Rental w/ Balcony!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the beauty of Wintergreen Resort, VA, and indulge in a memorable stay at this 2-bedroom, 2-bathroom vacation re ...
From $222 per night (USD)
VRBO
From $181 per night (USD)
VRBO
Queen City Hideaway - walk downtown, newly reno, classic, and cozy with views!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our charming short-term rental in downtown Staunton, Virginia! Nestled in the heart of this historic city, ou ...
From $181 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Cozy Craftsman: Newly Renovated/Downtown Staunton
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Cozy Craftsman is a newly renovated home located on the north end of Staunton, less than 1 mile to downtown and less tha ...
From $235 per night (USD)
Expedia
From $185 per night (USD)
VRBO
Shenandoah Valley Atelier: NEW Waynesboro Loft
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Shenandoah Valley Atelier is downtown Waynesboro's newest short-term rental. Located on the top floor of the Shenandoah ...
From $185 per night (USD)
VRBO
From $809 per night (USD)
Expedia
The Getaway at Wintergreen Resort
Bedrooms:
6
Bathrooms:
7
Sleeps:
23
Welcome to Escape to Blue Ridge Haven on Wintergreen Resort, your peaceful mountain getaway! Whether you're looking for ...
From $809 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Pet-Friendly Wintergreen Resort Condo w/ Patio!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Your dream mountain getaway awaits at this Wintergreen Resort vacation rental where you can enjoy sunny days or snowy sl ...
From $303 per night (USD)
VRBO
From $286 per night (USD)
VRBO
Lovely Apartment on theHill
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Completely renovated cozy 2 bedroom apartment short walk to Staunton’s historic downtown Woodrow Wilson Museum, Shakespe ...
From $286 per night (USD)
VRBO
From $307 per night (USD)
VRBO
2min to Ski! DogsOK Wood Stove Grill Fire Pit Hike
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Plucked from a German fairytale, this thoughtfully-designed oasis features intricate wainscoting and slate floors. Sense ...
From $307 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Serenity Ridge, Hot Tub, Views, Vineyards-Gameroom PRIVATE
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
About this space Serenity Ridge offers the perfect escape on your own little secluded ridge in the country. This home fe ...
From $284 per night (USD)
Expedia
From $447 per night (USD)
VRBO
2min to Ski Hot Tub EV Charger Mountain View DogOK
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 $447 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Gypsy Haven: Walk Downtown + Sunroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come play at the irresistible Gypsy Haven! There are almost too many special touches to list – from the extravagant weig ...
From $159 per night (USD)
Expedia
From $159 per night (USD)
VRBO
The Urban Cowboy Suite: Walk Downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Indulge yourself in our plush Urban Cowboy Suite on your next trip to Staunton! You’ll love the thoughtful details, the ...
From $159 per night (USD)
VRBO
From $156 per night (USD)
Expedia
The Pop Inn: Family Destination, Walk Dwntwn
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The design of the Pop Inn will pull you in, but the luxurious comfort and remarkable amenities will make you want to ext ...
From $156 per night (USD)
Expedia
From $192 per night (USD)
VRBO
The Overlook: Walk Downtown + City Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Live like a local on your next visit to Staunton Virginia! This newly remodeled apartment featuring mid-century modern d ...
From $192 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Grey Pine Lodge | Queen Comfort | BEST Location & Amenities!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Grey Pine Lodge is the boutique motel experience you're looking for! BEST LOCATION -Across the street from the popular ...
From $204 per night (USD)
Expedia
From $226 per night (USD)
VRBO
Grey Pine Lodge | King Deluxe | BEST Location & Amenities!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Grey Pine Lodge is the boutique motel experience you're looking for! BEST LOCATION -Across the street from the popular ...
From $226 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Grey Pine Lodge | King Deluxe | Pet-Friendly! | BEST Location & Amenities!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Grey Pine Lodge is the boutique motel experience you're looking for! This is a pet-friendly room category. Please indic ...
From $223 per night (USD)
Expedia
From $211 per night (USD)
VRBO
Grey Pine Lodge | King Classic | BEST Location & Amenities!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Grey Pine Lodge is the boutique motel experience you're looking for! BEST LOCATION -Across the street from the popular ...
From $211 per night (USD)
VRBO
From $236 per night (USD)
Expedia
Grey Pine Lodge | Queen/Queen | Pet-Friendly! | BEST Location & Amenities!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Grey Pine Lodge is the boutique motel experience you're looking for! This is a pet-friendly room category. Please indic ...
From $236 per night (USD)
Expedia
From $209 per night (USD)
VRBO
Grey Pine Lodge | King Classic | Pet-Friendly! | BEST Location & Amenities!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Grey Pine Lodge is the boutique motel experience you're looking for! This is a pet-friendly room category. Please indic ...
From $209 per night (USD)
VRBO
From $231 per night (USD)
Expedia
Grey Pine Lodge | Queen/Queen | BEST Location & Amenities!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Grey Pine Lodge is the boutique motel experience you're looking for! BEST LOCATION -Across the street from the popular ...
From $231 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Grey Pine Lodge | King Classic ADA Accessible | Pet-Friendly! | BEST Location & Amenities!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Grey Pine Lodge is the boutique motel experience you're looking for! This is a pet-friendly room category. Please indic ...
From $261 per night (USD)
VRBO
From $201 per night (USD)
Expedia
The Nest: Cozy Staunton Apartment + Walk Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Need a quiet respite? Relax into The Nest’s mid-century modern décor for a luxurious getaway. LIVING ROOM: sleeper sof ...
From $201 per night (USD)
Expedia
From $870 per night (USD)
VRBO
Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly
Bedrooms:
3
Bathrooms:
6
Sleeps:
16
Welcome to "Above the Clouds", your year-round retreat in the heart of Wintergreen. Our spacious house, nestled just min ...
From $870 per night (USD)
VRBO
From $166 per night (USD)
Expedia
The Bohemian Suite: Walk Downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Add a little free-spirited adventure to your travels with a stay in our Bohemian Suite! Whether you’re in town for busin ...
From $166 per night (USD)
Expedia
From $158 per night (USD)
VRBO
The Serendipity Suite: Walk Downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Serendipity means finding something wonderful when you aren't expecting it, and that is exactly what you will feel the m ...
From $158 per night (USD)
VRBO
From $164 per night (USD)
Expedia
The Bons Amis Suite: Walk Downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Bons Amis Suite means “The Good Friends Suite” in French. It has been lovingly furnished, decorated, and named in ho ...
From $164 per night (USD)
Expedia
From $466 per night (USD)
VRBO
The Pool House: Hot Tub + Pool + 15 mins downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
The Pool House is an open-concept space with a lofted bedroom. Below you will find a detailed layout of each space and i ...
From $466 per night (USD)
VRBO
From $166 per night (USD)
Expedia
The Shenandoah Suite: Walk Downtown!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Shenandoah Suite is an upbeat tribute to our beloved Shenandoah Valley! Designed to embrace you with the valley’s fe ...
From $166 per night (USD)
Expedia
From $337 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 $337 per night (USD)
VRBO
From $423 per night (USD)
Expedia
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 $423 per night (USD)
Expedia
From $356 per night (USD)
VRBO
Cozy Cabin in the Wintergreen Retreat Collection of Fine Homes
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Escape to bespoke, rustic luxury in the heart of Wintergreen Resort! Come enjoy our beautifully decorated, authentic l ...
From $356 per night (USD)
VRBO
From $305 per night (USD)
Expedia
5 Bedroom Home, 13 mins away from Skyline Drive
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
Bring the whole family to this great place with lots of room for fun. 5 Bedrooms, 2 full bathroom, 2 half bathrooms, a 1 ...
From $305 per night (USD)
Expedia
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VRBO
Mountain Top Getaway
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Enjoy the leaves, the snow, the skiing, the seasonal views in this top floor quiet 3 bedroom / 3 bath mountain retreat. ...
Click For Pricing
VRBO
From $514 per night (USD)
VRBO
5 min from slopes. Luxury Wintergreen Mt Home + All the Amenities!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Come escape to our luxury Mountain Home where you can enjoy year around! Our 3100 sq ft home offers 4 bdr & 3.5 bth, sle ...
From $514 per night (USD)
VRBO
From $538 per night (USD)
VRBO
5-Star, 4BR/4BA Rustic Lodge w/ HotTub! Great for couples weekend.
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Looking for rustic, mountain lodge perfect for a Guy or Gals weekend or a wedding/family gathering? We have you covered! ...
From $538 per night (USD)
VRBO
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Expedia
Spacious suite near DOWNTOWN
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cozy, private and spacious suite located in a tranquil and beautiful neighborhood. The place is just minutes to Historic ...
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Expedia
From $217 per night (USD)
VRBO
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 $217 per night (USD)
VRBO
From $270 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 $270 per night (USD)
VRBO
From $306 per night (USD)
VRBO
Newtown Retreat: Award-Winning Renovation + Ideal Location
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Prepare an elaborate meal in the spacious, fully equipped kitchen. Relax on the front porch as the sun sets behind the n ...
From $306 per night (USD)
VRBO
From $390 per night (USD)
Expedia
The Cardinal House: Historic Home on Tree Streets
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Located in the beautiful tree streets of downtown Waynesboro, The Cardinal House is a stunning 5 bed, 3 bath house with ...
From $390 per night (USD)
Expedia
From $1375 per night (USD)
VRBO
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 $1375 per night (USD)
VRBO
From $919 per night (USD)
Expedia
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 $919 per night (USD)
Expedia
From $393 per night (USD)
VRBO
HOT TUB! Soak into the Heart of Nelson County / Hosted by Heather
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Papa’s Cottage is a warm and inviting retreat in the heart of Afton, just minutes from popular vineyards, the Blue Ridge ...
From $393 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Cozy Getaway | Near Veritas & Blue Ridge Tunnel | Modern Comforts
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Meme’s Cottage is a peaceful Afton retreat surrounded by vineyards, mountain views, and scenic trails. Inside, you’ll fi ...
From $302 per night (USD)
Expedia
From $937 per night (USD)
VRBO
Luxury Designer Home, Dome and Top amenities
Bedrooms:
3
Bathrooms:
6
Sleeps:
16
Welcome to Wintergreen - Mountain View Retreat! Discover the latest listing in Wintergreen – a spacious mountain retreat ...
From $937 per night (USD)
VRBO
From $375 per night (USD)
Expedia
4min to Ski: Hot Tub Dogs OK PacMan Foosball Grill
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
4min to ski, walk to trails! Endless activities: apple picking, breweries/wineries, hiking, lake, horseback, golf, tenni ...
From $375 per night (USD)
Expedia
$3min to Ski! Mntn View Fireplace 55\TV w/ Disney+$
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VRBO
3min to Ski! Mntn View Fireplace 55\"TV w/ Disney+
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
3 min to Wintergreen ski slopes. Relax & enjoy the Blue Ridge Mountains in the heart of Wintergreen Resort! Perfect for ...
Click For Pricing
VRBO
$5 min to Ski: Hot Tub EV Charger Golden Tee 60\TV$
From $473 per night (USD)
Expedia
5 min to Ski: Hot Tub EV Charger Golden Tee 60\"TV
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 $473 per night (USD)
Expedia
From $508 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 $508 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Downtown Luxe: Luxury Vintage + Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
LIVING ROOM: sleeper sofa, accent chairs, smart TV EAT-IN-KITCHEN: fully stocked kitchen with oven, fridge, microwave, ...
From $254 per night (USD)
Expedia
From $458 per night (USD)
VRBO
Mountain House Overlooking Rockfish Valley
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unique octagonal house offering incredible views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 ...
From $458 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Cozy Lodge with view- Wintergreen Ski Chalet - 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 $428 per night (USD)
Expedia
From $218 per night (USD)
VRBO
Whimsical Creekside Cabin
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Escape to our cabin in the Blue Ridge Mountains! Fall asleep to sounds of Little Mary’s Creek, enjoy your coffee on the ...
From $218 per night (USD)
VRBO
From $850 per night (USD)
Expedia
4min to Ski! Mntn View Hot Tub EV Charger Grill
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
4min drive to Wintergreen skiing. Secluded farmhouse-style with views in every room. Hiking, breweries/vineyards, fishin ...
From $850 per night (USD)
Expedia

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