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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

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 ฿3,895
฿10,845 total
includes taxes & fees
26 Apr - 27 Apr
Wintergreen Ski Resort Condo w/ Golf Access!
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 ฿5,396
฿12,446 total
includes taxes & fees
20 Apr - 21 Apr
Blackwood Chalet
Luxury Room, Ensuite (The Storefront) | 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 ฿4,758
฿7,244 total
includes taxes & fees
20 Apr - 21 Apr
The Storefront
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
9.4 out of 10, Exceptional, (55 reviews)
"Always a pleasant stay."
United States
MARJORIE
The price is ฿2,650
฿2,950 total
includes taxes & fees
23 Apr - 24 Apr
Affordable Suites of America Waynesboro
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 ฿12,293
฿13,805 total
includes taxes & fees
20 Apr - 21 Apr
Afton Mountain Vineyards
Street view

Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (222 reviews)
"Nice place"
United States
Orhan
The price is ฿3,640
฿4,051 total
includes taxes & fees
20 Apr - 21 Apr
Valley Extended Suites
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 ฿7,823
฿19,422 total
includes taxes & fees
21 Apr - 22 Apr
Modern Nellysford Getaway on 40 Private Acres!
Apartment | 4 bedrooms

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is ฿6,446
฿17,053 total
includes taxes & fees
20 Apr - 21 Apr
Stoney Creek Cottage Wintergreen w EV Charger
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, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is ฿4,629
฿7,114 total
includes taxes & fees
18 May - 19 May
Love Ridge Mountain Lodging
Private kitchen

Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
The price is ฿3,672
฿6,753 total
includes taxes & fees
22 Apr - 23 Apr
Fishersville Oasis
Apartment, Private Bathroom (The Urban Cowboy) | Exterior

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 ฿2,842
฿5,686 total
includes taxes & fees
20 Apr - 21 Apr
The Urban Cowboy
Apartment, Private Bathroom (North Central Loft) | 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 ฿6,226
฿13,232 total
includes taxes & fees
20 Apr - 21 Apr
North Central Loft
Apartment, Private Bathroom (The Serendipity Suite) | 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 ฿2,842
฿5,686 total
includes taxes & fees
20 Apr - 21 Apr
The Serendipity Suite
Apartment, Private Bathroom (The Bohemian 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 ฿2,842
฿5,686 total
includes taxes & fees
20 Apr - 21 Apr
The Bohemian Suite
Apartment, Private Bathroom (The Shenandoah 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 ฿2,906
฿5,758 total
includes taxes & fees
4 May - 5 May
The Shenandoah Suite
Apartment, Private Bathroom (The Bons Amis 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 ฿2,842
฿5,686 total
includes taxes & fees
4 May - 5 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

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.