Wintergreen Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Wintergreen holiday rentals

Front of property

Wintergreen Ski Resort Condo w/ Golf Access!

Wintergreen Ski Resort Condo w/ Golf Access!
4.0 star property
Nellysford
10.0 out of 10, Exceptional, (2 reviews)
"Really nice and convenient condo. Great amenities. Would definitely stay again."
United States
Matthew
The price is HK$955
HK$2,659 total
includes taxes & fees
21 May - 22 May
Wintergreen Ski Resort Condo w/ Golf Access!
Lounge

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is HK$1,253
HK$2,973 total
includes taxes & fees
21 May - 22 May
Blackwood Chalet
Private kitchen

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.4 out of 10, Exceptional, (57 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is HK$619
HK$689 total
includes taxes & fees
17 May - 18 May
Affordable Suites of America Waynesboro
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (235 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is HK$785
HK$874 total
includes taxes & fees
18 May - 19 May
Valley Extended Suites
Bathroom

North Central Loft

North Central Loft
2.0 star property
Staunton
10.0 out of 10, Exceptional, (5 reviews)
"Clean, comfortable, fun, well appointed and thoughtful details. A great place. "
United States
Stacey
The price is HK$1,527
HK$3,246 total
includes taxes & fees
25 May - 26 May
North Central Loft
Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is HK$1,107
HK$1,713 total
includes taxes & fees
15 Jun - 16 Jun
Love Ridge Mountain Lodging
Interior detail

Afton Mountain Vineyards

Afton Mountain Vineyards
2.5 star property
Afton
10.0 out of 10, Exceptional, (2 reviews)
"Cozy and comfortable with pond and mountain views. Wine tasting on site and easy access to Wintergreen. We loved our stay and will be back again!"
United States
Jennifer
The price is HK$3,278
HK$3,681 total
includes taxes & fees
26 May - 27 May
Afton Mountain Vineyards
4 bedrooms

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is HK$1,523
HK$3,794 total
includes taxes & fees
18 May - 19 May
Stoney Creek Cottage Wintergreen w EV Charger
Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is HK$1,919
HK$4,764 total
includes taxes & fees
20 May - 21 May
Modern Nellysford Getaway on 40 Private Acres!
1 bedroom

The Urban Cowboy

The Urban Cowboy
2.0 star property
Staunton
8.6 out of 10, Excellent, (7 reviews)
"Great place to stay very organized and has everything you need super clean !"
United States
Philip
The price is HK$697
HK$1,395 total
includes taxes & fees
27 May - 28 May
The Urban Cowboy
Balcony view

The Serendipity Suite

The Serendipity Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (7 reviews)
"We loved staying at the Serendipity Suite in beautiful Staunton! It's a lovely apartment and our hosts made us feel so comfortable with all of the little thoughtful extras."
United States
Patricia
The price is HK$862
HK$1,579 total
includes taxes & fees
25 May - 26 May
The Serendipity Suite
Lobby

The Bohemian Suite

The Bohemian Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6 reviews)
"It was really nice. A bit pricey. "
United States
Bonny
The price is HK$721
HK$1,421 total
includes taxes & fees
8 Jun - 9 Jun
The Bohemian Suite
Exterior

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (58 reviews)
"Great location, fun place to stay!"
United States
Carol
The price is HK$1,167
HK$1,776 total
includes taxes & fees
17 May - 18 May
The Storefront
Private kitchen

Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
The price is HK$900
HK$1,656 total
includes taxes & fees
8 Jun - 9 Jun
Fishersville Oasis
Exterior

The Shenandoah Suite

The Shenandoah Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (8 reviews)
"This was our second stay at this property (in a different apartment), and once again it did not disappoint. The space was clean, comfortable, and the kitchen was stocked with basic cooking items, though spices were minimal. The location is a big plus—easy walking distance to downtown restaurants—and we would definitely stay here again."
United States
Carrie
The price is HK$697
HK$1,395 total
includes taxes & fees
26 May - 27 May
The Shenandoah Suite
Exterior

The Bons Amis Suite

The Bons Amis Suite
2.0 star property
Staunton
9.6 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay. The room is vey nice and the location is convenient to the conference center nearby."
United States
John
The price is HK$697
HK$1,394 total
includes taxes & fees
26 May - 27 May
The Bons Amis Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Wintergreen Hotel Reviews

Best views on Mountain! Breathtaking 5 Star condo! Book Summer and Fall now!

Best views on Mountain! Breathtaking 5 Star condo! Book Summer and Fall now!

10/10 Excellent
"Had the best time and loved our location. Watched the sunrise every morning from the amazing deck view. Looking forward to booking again on our next visit. "
Timmie T. 3-night trip
Posted 2 days ago
Best views on Mountain! Breathtaking 5 Star condo! Book Summer and Fall now!

Find out more about Wintergreen

Search for holiday rentals in Wintergreen on Expedia! You can easily find your home rentals, villas, holiday apartments in Wintergreen using one of the methods below:

  • View our selection of featured holiday rentals in Wintergreen
  • Use the map to find apartments and other holiday homes in the Wintergreen neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wintergreen while they last

Look no further and take a look at our great range of rental properties in Wintergreen!

Frequently asked questions

Can I find holiday rentals in Wintergreen?

Yes, there are holiday rentals close to the most popular sights in Wintergreen, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffee shops during your trip.

What are some of the best holiday rentals that Wintergreen has to offer?

Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope: This highly rated holiday home rental in Wintergreen is located in the mountains, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other top choices in Wintergreen are 4 BR cabin mins to trails & breweries pets welcome and Upscale and Family-Friendly in Wintergreen.

How many holiday rentals are there in Wintergreen?

Choose from 224 Expedia holiday rentals in Wintergreen for a memorable holiday.

What can I see and do in Wintergreen?

While exploring the area, visit family-friendly sights like War Fields, or get outside and enjoy nature at George Washington National Forest. While here, Bold Rock Hard Cider Nellysford Cidery and Stoney Creek Golf Course are other places worth a visit.

What’s a holiday rental in Wintergreen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wintergreen. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway.