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Vacation Rentals in Wintergreen, Virginia

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about Wintergreen

Wintergreen, Virginia Vacation Rentals and Tourism

It’s hard to emphasize just one “pro” to staying in Wintergreen vacation rentals. That’s because the famed Wintergreen resort is in full steam throughout the year. See the stunning view from up top the Blue Ridge Mountains by golfing on Devils Knob Golf Course, relaxing at the Wintergreen Spa, or of course skiing! No matter what season you visit Virginia’s darling mountain town, Wintergreen rentals are here to shelter you and your family.

Pack some skis or perhaps a snowboard and head to a Wintergreen ski condo, or get your golf gear ready and find a Wintergreen vacation rental near the golf course. Wintergreen vacation rentals will appease every age group and every type of traveler, but that also means they’re popular. It’s best to plan out your Wintergreen, VA vacation well in advance.

From skier-friendly Wintergreen condo rentals to rustic Wintergreen cabin vacation rentals, you’re sure to find your choice accommodations right here. Wintergreen vacation homes are in demand, so there happen to be lots to choose from!

Wintergreen Vacation Rental Deals

Spread across 11,000 acres, the Wintergreen area is the premier winter getaway in Virginia. With amazing skiing and winter sports, you are sure to find something that will captivate you here. And if you stay in one of our Wintergreen discounted vacation rentals you can have fun and save money doing it. And with our discounted rates and Wintergreen last minute deals, you are sure to get the best value out of your vacation here. So come and see what Wintergreen and create memories that will last you a lifetime.

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

Wintergreen things to do

 

Wintergreen Winery

Awesome wines, beautiful setting, amazing hospitality ... how could you go wrong? It is a must visit trip to Virginia wine country. Take the back roads...read more

 

Veritas Winery & Vineyard

Gorgeous location for a wedding! My friends had their wedding here and it was a beautiful location. The ceremony was outside. There were white chairs set...read more

 

Hill Top Berry Farm & Winery

Definitely worth a visit, especially if your looking for something different. We left with a bottle of their Virginia peach wine. Just like a fresh peach!read more

 

Flying Fox Vineyard

The wines were good and the lesson on tanins and why they're important was very informative. The host was quite good at explaining the finey parts of the...read more

 

Pollak Vineyards

If you saw 8 potential customers walk in your door, who are paying for a tasting, wouldn't you treat them in a way that makes them want to buy from...read more

 

Afton Mountain Vineyards

Very beautiful area to enjoy, but I'm just so tired of going to tastings and being served by pretentious servers. I ignored it and even accepted as a novice...read more

 

Allen Creek Nature Preserve

Allen Creek Nature Preserve is located on the corner of Stoney Creek East and Towhee Court next to one of the holes of Stoney Creek Golf Course. Parking is...read more

 

Lovingston Winery

Holy hidden gem awesomeness! Okay, I must admit, after looking a host of David R.'s price-centric reviews, I thought he just might be biased on this place...read more

 

Cardinal Point Vineyard & Winery

I revisited this place last weekend after my initial visit several years ago. This place has definitely increased in quality. We tried a all the wines,...read more

 

Mountain Cove Vineyards

The oldest winery open to the public in the state (open since 1973). Lots of land to spread out. Gazebo, tent for events, and mountains on all sides....read more

 

Appalachian Trail - Rockfish Gap Trailhead

There are few places in the world that can elicit a feeling of pure joy, nervousness and excitement as much as the Appalachian Trail. A few years back I...read more

 

Anytime Fitness

Not sure what Emilie A.'s issues are. This place rocks! The staff are the most educated and knowledgable in Waynesboro and are always willing to help!...read more

 

South River Fly Shop

Awesome independent fly shop! Tom and Kevin are both incredibly knowledgeable and friendly. If you're in Waynesboro, stop in and get what you need.read more

 

P. Buckley Moss Museum

I'm a fan of the simple american art that P. Buckley Moss provides. Her museum serves as a gallery to showcase her art and a few times a year she will sit...read more

 

Democracy Vineyards

We have another winner in Nelson Country, that hip area between Charlottesville and Lynchburg that is now home to at least 8 wineries and four breweries....read more

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DEAL!! Hot Tub/Steps to Eagles Swoop/WiFi/Grill/Ski In/Guest Pass
Wintergreen House Rental Picture
  • House Rental Deals and Discounts $50 off = $1,150 per week
  • bedrooms 3
  • community Wintergreen Resort
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $200 - $450 /nt
    $1,200 - $1,300 /wk
 
 
 
 
 

89 reviews write a review

DEAL!! Timbers Ski In/Ski Out
Wintergreen Studio Rental Picture
  • Studio Rental Deals and Discounts free night valued at USD $100
  • bedrooms 1
  • community Timbers
  • rental type Studio
  • sleeps 2
  • baths 1
  • rates (USD) $100 - $200 /nt
    $500 - $800 /wk
 
 
 
 
 

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Wintergreen Family Vacation Home with WiFi & Resort Passes
Wintergreen House Rental Picture
  • bedrooms 3
  • community Wintergreen Resort
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $200 - $250 /nt
    $1,250 - $1,400 /wk
    $3,250 - $3,250 /mth
 
 
 
 
 

30 reviews write a review

The Wintergreen Chalet
Wintergreen House Rental Picture
  • bedrooms 6
  • community Wintergreen Resort
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD) $299 - $699 /nt
    $1,999 - $2,999 /wk
 
 
 
 
 

17 reviews write a review

Cozy Home with Beautiful Views, Ski In/Out
Wintergreen House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $125 - $375 /nt
    $750 - $1,500 /wk
 
 
 
 
 

90 reviews write a review

4 Season Get Away
Wintergreen Condo Rental Picture
  • bedrooms 2
  • community Eagles Court Condos
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $175 - $175 /nt
    $700 - $1,400 /wk
    $1,200 - $3,000 /mth
 
 
 
 
 

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Skimoor - Ski-In/Ski-Out (1st Floor)
Wintergreen Condo Rental Picture
  • bedrooms 2
  • community Eagles Court
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $250 - $300 /nt
    $1,050 - $2,100 /wk
 
 
 
 
 

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SkiDobie - Beautiful views & easy access to the Dobie Slopes
Wintergreen Condo Rental Picture
  • bedrooms 3
  • community Dobie Condo
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,750 - $2,550 /wk
    $3,500 - $4,000 /mth
 
 
 
 
 

2 reviews write a review

A Beautiful Mountain Getaway
Wintergreen Condo Rental Picture
  • bedrooms 3
  • community Wintergreen Resort
  • rental type Condo
  • sleeps 8
  • baths 3
  • rates (USD) $250 - $300 /nt
    $1,650 - $2,000 /wk
 
 
 
 
 

1 reviews write a review

Shadow Mountain Rentals
Wintergreen Cabin Rental Picture
  • bedrooms 2
  • community Crabtree Falls
  • rental type Cabin
  • sleeps 8
  • baths 2
  • rates (USD) $135 - $210 /nt
    $1,250 - $1,250 /wk
    $4,400 - $5,000 /mth
 
 
 
 
 

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Fantastic Views from House & Deck, Close to Slopes & Lodge!!
Wintergreen House Rental Picture
  • bedrooms 4
  • community Wintergreen
  • rental type House
  • sleeps 14
  • baths 2
  • rates (USD) $1,600 - $1,900 /wk
 
 
 
 
 

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