Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Wintergreen holiday rentals

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 RM572
RM1,432 total
includes taxes & fees
10 Mar - 11 Mar
Blackwood Chalet
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 RM482
RM1,341 total
includes taxes & fees
10 Mar - 11 Mar
Wintergreen Ski Resort Condo w/ Golf Access!
Lounge

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 RM588
RM896 total
includes taxes & fees
10 Mar - 11 Mar
The Storefront
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 RM1,382
RM1,552 total
includes taxes & fees
10 Mar - 11 Mar
Afton Mountain Vineyards
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (217 reviews)
"Clean room great location quiet area"
United States
Krista
The price is RM450
RM501 total
includes taxes & fees
10 Mar - 11 Mar
Valley Extended Suites
4 bedrooms

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is RM593
RM1,800 total
includes taxes & fees
10 Mar - 11 Mar
Stoney Creek Cottage Wintergreen w EV Charger
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 RM490
RM788 total
includes taxes & fees
10 Mar - 11 Mar
Love Ridge Mountain Lodging
Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is RM967
RM2,401 total
includes taxes & fees
24 Mar - 25 Mar
Modern Nellysford Getaway on 40 Private Acres!
Miscellaneous

Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
The price is RM454
RM835 total
includes taxes & fees
10 Mar - 11 Mar
Fishersville Oasis
4 bedrooms

Waynesboro Home Near Wintergreen Charlottesville

Waynesboro Home Near Wintergreen Charlottesville
2.0 star property
Waynesboro
The price is RM954
RM2,769 total
includes taxes & fees
10 Mar - 11 Mar
Waynesboro Home Near Wintergreen Charlottesville
Bathroom

North Central Loft

North Central Loft
2.0 star property
Staunton
10.0 out of 10, Exceptional, (4 reviews)
"Clean, comfortable, fun, well appointed and thoughtful details. A great place. "
United States
Stacey
The price is RM770
RM1,636 total
includes taxes & fees
10 Mar - 11 Mar
North Central Loft
Exterior

The Serendipity Suite

The Serendipity Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6 reviews)
"Everything from start to finish was great"
United States
Heidi
The price is RM351
RM703 total
includes taxes & fees
10 Mar - 11 Mar
The Serendipity Suite
Exterior

The Urban Cowboy

The Urban Cowboy
2.0 star property
Staunton
8.6 out of 10, Excellent, (7 reviews)
"The space,the location,the parking,the details! It truly felt like my apartment away from home! This place is a must stay!"
United States
Dorothy
The price is RM351
RM703 total
includes taxes & fees
12 Mar - 13 Mar
The Urban Cowboy
Interior

Secret Garden Studio

Secret Garden Studio
2.0 star property
Staunton
9.4 out of 10, Exceptional, (3 reviews)
"Great studio, more spacious than I expected. Great thought put into design and decor! Hosts were very responsive and I would definitely rent again!"
United States
Kathleen
The price is RM316
RM650 total
includes taxes & fees
19 Mar - 20 Mar
Secret Garden Studio
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 RM351
RM703 total
includes taxes & fees
17 Mar - 18 Mar
The Bohemian Suite
Exterior

The Shenandoah Suite

The Shenandoah Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (6 reviews)
"Well-appointed, large space conveniently located within walking distance to downtown. Comfy bed and all the expected amenities. Excellent communication. "
United States
Jani
The price is RM351
RM703 total
includes taxes & fees
10 Mar - 11 Mar
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)
"Quiet homey environment in a great location. Clean and cozy. Really appreciated the coffee and other amenities. Would definitely stay here again !"
United States
Areej
The price is RM351
RM703 total
includes taxes & fees
23 Mar - 24 Mar
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

Find out more about Wintergreen

Search for holiday rentals in Wintergreen on Expedia.co.uk! 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.

How many holiday rentals are there in Wintergreen?

Choose from 225 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.