Vacation Rentals in Wintergreen, Virginia
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.
more destinations
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
-
$50 off = $1,150 per week
- bedrooms 3
- community Wintergreen Resort
- rental type House
owner badge
- sleeps 6
- baths 2
- rates (USD)
$200
- $450
/nt
$1,200 - $1,300 /wk
-
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
- bedrooms 3
- community Wintergreen Resort
- rental type House
owner badge
- sleeps 8
- baths 2
- rates (USD)
$200
- $250
/nt
$1,250 - $1,400 /wk
$3,250 - $3,250 /mth
- bedrooms 6
- community Wintergreen Resort
- rental type House
owner badge
- sleeps 14
- baths 4½
- rates (USD)
$299
- $699
/nt
$1,999 - $2,999 /wk
- bedrooms 3
- community
- rental type House
owner badge
- sleeps 7
- baths 2
- rates (USD)
$125
- $375
/nt
$750 - $1,500 /wk
- bedrooms 2
- community Eagles Court Condos
- rental type Condo
- sleeps 6
- baths 1½
- rates (USD)
$175
- $175
/nt
$700 - $1,400 /wk
$1,200 - $3,000 /mth
- bedrooms 2
- community Eagles Court
- rental type Condo
- sleeps 6
- baths 1½
- rates (USD)
$250
- $300
/nt
$1,050 - $2,100 /wk
- bedrooms 3
- community Dobie Condo
- rental type Condo
owner badge
- sleeps 8
- baths 3
- rates (USD)
$1,750
- $2,550
/wk
$3,500 - $4,000 /mth
- bedrooms 3
- community Wintergreen Resort
- rental type Condo
- sleeps 8
- baths 3
- rates (USD)
$250
- $300
/nt
$1,650 - $2,000 /wk
- 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
- bedrooms 4
- community Wintergreen
- rental type House
- sleeps 14
- baths 2
- rates (USD)
$1,600
- $1,900
/wk






