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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

 

Albemarle CiderWorks

This was our first experience at a cider cellar. It was great. Currently they are doing construction to expand their tasting room however their product is...read more

 

Wisdom Oak Winery

Great staff, very knowledgeableread more

 

Pippin Hill Farm & Vineyards

First off, the view is truly spectacular. You should make a stop just to check it out. We came for a wine tasting and for lunch. It was buzzing with people...read more

 

Mountfair Vineyards

My wife and I took local roads (33 to 810) from Massanutten resort near Harrisonburg and had a picturesque hour-long ride through Shenandoah National Park...read more

 

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

 

Blenheim Vineyards

I'm not sure why they didn't have these the first time I was here, but we were here this past weekend and I was very happy to see ample amounts of seating!...read more

 

Flying Fox Vineyard

The lady working here was incredibly rude. The wine was terrible compared to other vineyards in the area.read more

 

Veritas Winery & Vineyard

Great experience! And good wine too! We had a very knowledgable and cool person do the wine tasting for us.. I forget his name damnit. He taught us how to...read more

 

Jefferson Vineyards

We came by here around 11am on a Friday. When we walked in, we just kind of stood by the door because it wasn't clear what exactly to do. After about 2...read more

 

Satchidananda Ashram Yogaville

This place is out in the boonies for real BUT that is not a bad thing per say if you are staying for the reasons it is intended for. Like other reviewers...read more

 

Stonewall Jackson House

If not for the Civil War, Thomas Jackson would have been pretty much forgotten as a participant in the Mexican American War and a very religious, but...read more

 

Barboursville Vineyards

We went on a Saturday, around 11AM, before the crowds arrived and we really loved the layout of the tasting room and the way the tastings work. You buy your...read more

 

Ashtanga Yoga Charlottesville

I found Ashtanga Yoga through Crossfit Charlottesville, who hosted a special yoga class with Annie R. The class was excellent, so I asked Annie where she...read more

 

Amazement Square

Worth the trip from anywhere in Southwest Virginia. Especially worth it on Thursday, when admission is discounted. Doesn't look like much from the street,...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

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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

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

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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MOUNTAIN HOUSE - 3rd night free
Wintergreen House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $275 - $675 /nt
    $1,300 - $2,200 /wk
    $2,750 - $3,500 /mth
 
 
 
 
 

32 reviews write a review

Comfort and charm on top of Wintergreen Mountain Resort
Wintergreen House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $200 - $400 /nt
    $1,225 - $2,450 /wk
 
 
 
 
 

17 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) $200 - $400 /nt
    $1,300 - $2,000 /wk
 
 
 
 
 

28 reviews write a review

Huge house on 16th Green - Pets OK
Wintergreen House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths 0
  • rates (USD) $195 - $395 /nt
    $980 - $1,875 /wk
 
 
 
 
 

22 reviews write a review

Stunning, Creekside, Mountain Top Home, Golf, Internet, Phone, Stone Fireplace
Wintergreen House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $275 - $350 /nt
    $1,000 - $1,500 /wk
 
 
 
 
 

11 reviews write a review

Beautiful 5 BR House with Hot Tub
Wintergreen House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $300 - $450 /nt
    $1,900 - $2,500 /wk
 
 
 
 
 

15 reviews write a review

Discounted 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 - $350 /nt
    $1,000 - $1,700 /wk
 
 
 
 
 

5 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

Best Location & View on Mtn - Pets OK - ski in/out
Wintergreen Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $145 - $295 /nt
 
 
 
 
 

20 reviews write a review

Black Bear Lodge: End of Summer & Fall Special! Luxury House! Guest Passes!
Wintergreen House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $299 - $695 /nt
    $2,195 - $3,495 /wk
 
 
 
 
 

19 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
 
 
 
 
 

2 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)
 
 
 
 
 

22 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
 
 
 
 
 

5 reviews write a review

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

97 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 - $295 /nt
    $950 - $960 /wk
    $2,950 /mth
 
 
 
 
 

10 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)
 
 
 
 
 

37 reviews write a review

Serenity on top of Wintergreen Mountain Resort
Wintergreen House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths 4
  • rates (USD) $300 - $600 /nt
    $1,750 - $3,500 /wk
 
 
 
 
 

18 reviews write a review

Luxury Mountain Cabin With Majestic Views
Wintergreen Cabin Rental Picture
  • bedrooms 4
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $250 - $350 /nt
    $1,500 /wk
 
 
 
 
 

11 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
    $1,575 - $2,800 /wk
 
 
 
 
 

4 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 - $400 /nt
    $1,150 - $1,875 /wk
 
 
 
 
 

14 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
 
 
 
 
 

5 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

Enjoy Large Family Room, Pet Friendly
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

Premium mountain view home, huge fenced yard, 7-person hot tub, WPI Member Adv.
Wintergreen House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $550 - $725 /nt
    $3,500 - $5,000 /wk
 
 
 
 
 

3 reviews write a review

Luxury House on Mountain Golf Course - Sep 5th weekend available at discount
Wintergreen House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $250 - $400 /nt
    $1,500 - $1,800 /wk
    $3,750 - $4,000 /mth
 
 
 
 
 

21 reviews write a review

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

Pet Friendly 2BR Vacation Rental Near Blue Ridge Parkway and Wintergreen Resort
Wintergreen House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 8
  • baths 1
  • rates (USD) $129 - $159 /nt
    $894 /wk
    $3,000 /mth
 
 
 
 
 

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Summer In The Mountains
Wintergreen House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $150 - $295 /nt
    $700 - $900 /wk
 
 
 
 
 

24 reviews write a review

On a Clear Day You Can See Forever!
Wintergreen Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD)
 
 
 
 
 

19 reviews write a review

Rockfish Valley Farm Cottage at Elk Hill Near Wintergreen
Wintergreen Farmhouse Rental Picture
  • bedrooms 4
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD)
 
 
 
 
 

6 reviews write a review

Lucky Chalet #13
Wintergreen Chalet Rental Picture
  • bedrooms 3
  • rental type Chalet
  • sleeps 12
  • baths
  • rates (USD) $245 - $335 /nt
    $1,565 /wk
 
 
 
 
 

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