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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Wintergreen holiday rentals

Apartment (2 Bedrooms) | 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 ฿3,986
฿11,097 total
includes taxes & fees
5 Jun - 6 Jun
Wintergreen Ski Resort Condo w/ Golf Access!
Apartment, Private Bathroom (Laurelwood Hollow) | Exterior

Laurelwood Hollow

Laurelwood Hollow
2.0 star property
Nellysford
The price is ฿3,109
฿8,399 total
includes taxes & fees
5 Jul - 6 Jul
Laurelwood Hollow
Exterior

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is ฿8,168
฿16,511 total
includes taxes & fees
8 Jun - 9 Jun
Mountain Mindset
Condo, Private Bathroom (Mountain Vista View) | 1 bedroom

Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
The price is ฿4,548
฿8,415 total
includes taxes & fees
7 Jun - 8 Jun
Mountain View Vista
House, Private Bathroom (Red White Wintergreen) | 5 bedrooms

Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
The price is ฿14,692
฿29,361 total
includes taxes & fees
7 Jun - 8 Jun
Red White and Wintergreen
Condo, Private Bathroom (Panoramic Peak) | Exterior

Panoramic Peak

Panoramic Peak
2.0 star property
Nellysford
The price is ฿4,541
฿8,402 total
includes taxes & fees
7 Jun - 8 Jun
Panoramic Peak
Cabin, Private Bathroom (Blackwood Chalet) | 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 ฿5,530
฿13,560 total
includes taxes & fees
7 Jun - 8 Jun
Blackwood Chalet
Standard Suite, 1 Queen Bed | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.2 out of 10, Wonderful, (60 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is ฿2,581
฿2,873 total
includes taxes & fees
13 Jun - 14 Jun
Affordable Suites of America Waynesboro
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (241 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is ฿3,725
฿4,146 total
includes taxes & fees
17 Jun - 18 Jun
Valley Extended Suites
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 ฿12,748
฿14,317 total
includes taxes & fees
15 Jun - 16 Jun
Afton Mountain Vineyards
Cottage, Private Bathroom (Bluebird Cottage) | Exterior

Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is ฿3,757
฿8,806 total
includes taxes & fees
16 Jun - 17 Jun
Bluebird Cottage
House | 4 bedrooms

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is ฿7,872
฿17,163 total
includes taxes & fees
8 Jun - 9 Jun
Stoney Creek Cottage Wintergreen w EV Charger
House (3 Bedrooms) | Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is ฿8,005
฿19,874 total
includes taxes & fees
16 Jun - 17 Jun
Modern Nellysford Getaway on 40 Private Acres!
Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (17 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is ฿4,589
฿7,117 total
includes taxes & fees
9 Jun - 10 Jun
Love Ridge Mountain Lodging
House, Private Bathroom (Tucked Inn: Upper Unit) | Terrace/patio

Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
The price is ฿3,436
฿9,371 total
includes taxes & fees
7 Jun - 8 Jun
Tucked Inn: Upper Unit
Exterior

Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is ฿4,933
฿5,540 total
includes taxes & fees
16 Jun - 17 Jun
Branch and Barrel
Apartment, Private Bathroom (Magnolia Suite) | Exterior

Magnolia Suite

Magnolia Suite
2.0 star property
Staunton
The price is ฿3,365
฿6,219 total
includes taxes & fees
7 Jun - 8 Jun
Magnolia 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! 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
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  • 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 223 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.