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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

 

Hill Top Berry Farm & Winery

I was reluctant to visit this winery as I am not a real big fan of fruit wines, but this was a spectacular find. The fruit wines were not too sweet, and the...read more

 

Veritas Winery & Vineyard

9 wine tastings for $5 plus you get to keep the glass. Sit by the fireplace and take a sneak peak of the banquet room (it's gorgeous, they host lots of...read more

 

Flying Fox Vineyard

Flying fox is one of our favorite wineries around. Both their reds and whites are quite good. They also have quite reasonable prices and are always willing...read more

 

Wintergreen Winery

On a recent tip to Nelson county for a wine weekend, my husband and I tried this place, and we were not impressed at all. The view was nice, sure, but the...read more

 

Afton Mountain Vineyards

As you approach the car park, you begin to see the stunning setting for this winery overlooking the vines, a lake, and the mountains. We did a tasting of...read more

 

Pollak Vineyards

Great experience at Pollak during our wine tasting trip this February! The winery itself is spacious, clean and well-maintained with a great view of the...read more

 

Cardinal Point Vineyard & Winery

Cardinal Point is one of the best wineries in Virginia. Their selection of whites is especially notable (be sure to check out the Quattro. It's a little...read more

 

Lovingston Winery

Red wine fans, go here. Period. I've not enjoyed as many robust, rich reds at any other Virginia winery (out of several dozen I've visited). And the...read more

 

Mountain Cove Vineyards

Let me start with the positive: There was no charge for the tasting and the woman who poured our tasting was very friendly. She was, however, unable to...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

 

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

 

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

 

9 Rounds Fitness

Wow! If you are a fitness buff or just someone wanting to try something new!? Check this out! A new workout every three minutes for thirty mins straight!!...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

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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
 
 
 
 
 

91 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 /nt
    $700 - $1,400 /wk
    $1,200 - $3,000 /mth
 
 
 
 
 

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A Place to Stay in Crozet
Wintergreen House Rental Picture
  • bedrooms 1
  • community Neighborhood
  • rental type House
  • sleeps 3
  • baths 1
  • rates (USD) $110 - $120 /nt
    $500 - $600 /wk
    $1,800 - $2,000 /mth
 
 
 
 
 

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A Beautiful Mountain Getaway
Wintergreen Condo Rental Picture
  • bedrooms 3
  • community Wintergreen Resort
  • rental type Condo
  • sleeps 8
  • baths 3
  • rates (USD) $275 - $325 /nt
    $1,800 - $2,150 /wk
 
 
 
 
 

1 reviews write a review

Timbers Ski In/Ski Out
Wintergreen Studio Rental Picture
  • bedrooms 1
  • community Timbers
  • rental type Studio
  • sleeps 2
  • baths 1
  • rates (USD) $100 - $200 /nt
    $500 - $800 /wk
 
 
 
 
 

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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 /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
  • rental type House
  • sleeps 14
  • baths 2
  • rates (USD) $1,600 - $1,900 /wk
 
 
 
 
 

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Black Bear Lodge, now with guest passes!, summer special rates!
Wintergreen House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $349 - $695 /nt
 
 
 
 
 

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FANTASTICS VIEWS FROM HOUSE & DECK Please call for more info (804) 364-4663
Wintergreen House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths 2
  • rates (USD) $295 - $475 /nt
    $2,016 - $2,890 /wk
 
 
 
 
 

7 reviews write a review

Sprawling 6 BR/4.5 BA Home at the Top of the Resort
Wintergreen House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD)
 
 
 
 
 

19 reviews write a review

THE MOUNTAIN HOUSE - 3rd night free*
Wintergreen House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $175 - $400 /nt
    $1,000 - $1,800 /wk
    $3,500 - $5,000 /mth
 
 
 
 
 

31 reviews write a review

Large and Luxurious Exec 5BR House - Summer weeks $1,800!
Wintergreen House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $300 - $625 /nt
    $1,800 /wk
 
 
 
 
 

95 reviews write a review

Cozy 1 BR Mountain Getaway at Wintergreen Resort
Wintergreen Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 2
  • baths 2
  • rates (USD) $150 /nt
    $1,050 /wk
    $4,500 /mth
 
 
 
 
 

1 reviews write a review

Post&Beam/ Passes/wi-fi/Phone/Luxmattresses/2 masters/flat screen TV's,A/C
Wintergreen House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $175 - $500 /nt
    $1,300 - $2,600 /wk
 
 
 
 
 

27 reviews write a review

$1000/weekly rate - Luxury 4br Mountain Top Home W/ Beautiful Sunset Views
Wintergreen House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 11
  • baths 2
  • rates (USD) $200 - $325 /nt
    $1,000 - $1,050 /wk
 
 
 
 
 

5 reviews write a review

Wintergreen Home-Great for Families-Great Location
Wintergreen House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

36 reviews write a review

March/April Discount- Luxury House on Golf Course Near Slopes (WPI Pass)
Wintergreen House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $250 - $325 /nt
    $1,330 - $1,600 /wk
    $3,750 - $4,072 /mth
 
 
 
 
 

21 reviews write a review

Book Spring & Summer Now! -Top of Eagle Swoop, New Renovation, Free WiFi, HBO
Wintergreen Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $175 - $200 /nt
    $950 - $960 /wk
    $2,950 /mth
 
 
 
 
 

8 reviews write a review

Great Views from Home at Wintergreen!
Wintergreen Chateau_/_country_house Rental Picture
  • bedrooms 6
  • rental type Chateau / country house
  • owner badgeowner badge
  • sleeps 14
  • baths
  • rates (USD) $375 - $575 /nt
 
 
 
 
 

6 reviews write a review

Newly Renovated 2Br 2Ba Wintergreen Resort Mountain Condo
Wintergreen Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $115 - $250 /nt
    $700 - $1,300 /wk
 
 
 
 
 

2 reviews write a review

Family & Dog Friendly Spacious Mountain Home
Wintergreen House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $275 - $315 /nt
    $1,150 - $1,390 /wk
 
 
 
 
 

14 reviews write a review

Cub Creek Mt Getaway Near Wintergreen and the Blue Ridge Parkway
Wintergreen Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $85 - $115 /nt
    $375 - $600 /wk
    $900 - $1,250 /mth
 
 
 
 
 

5 reviews write a review

Beautiful 5-Bedroom Mountain Home
Wintergreen House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $300 - $500 /nt
    $1,400 - $2,800 /wk
 
 
 
 
 

4 reviews write a review

Mountaintop Condo - Spectacular Views!
Wintergreen Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 0
  • rates (USD) $200 /nt
 
 
 
 
 

4 reviews write a review

Enjoy Thanksgiving in the Mountain! Pets Welcome
Wintergreen House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 4
  • rates (USD) $250 - $425 /nt
    $1,400 - $2,250 /wk
    $5,250 - $5,303 /mth
 
 
 
 
 

4 reviews write a review