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Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Wintergreen vacation rentals

Cabin, Private Bathroom (Blackwood Chalet) | Exterior
Blackwood Chalet

Cabin in Nellysford

2.0 star property
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
The price is NT$5,270
NT$12,154 total
includes taxes & fees
Dec 14 - Dec 15
Blackwood Chalet
Studio Suite | Private kitchen | Full-size fridge, microwave, oven, stovetop
Valley Extended Suites

Apartment in Fishersville

3.0 star property
9.0 out of 10, Wonderful, (216)
"I liked the cleanliness of the suite, the fully staffed kitchen, the large bathroom, the comfortable bed, the ease and safety of the parking area."
United States
Tammy
The price is NT$3,555
NT$3,956 total
includes taxes & fees
Dec 14 - Dec 15
Valley Extended Suites
Apartment, Private Bathroom (The Bohemian Suite) | Lobby
The Bohemian Suite

Apartment in Staunton

2.0 star property
10.0 out of 10, Exceptional, (6)
"It was really nice. A bit pricey. "
United States
Bonny
The price is NT$2,775
NT$4,979 total
includes taxes & fees
Jan 5 - 2026/1/6
The Bohemian Suite
Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio
Love Ridge Mountain Lodging

Cabin in Montebello

3.0 star property
10.0 out of 10, Exceptional, (13)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is NT$5,601
NT$8,161 total
includes taxes & fees
Dec 11 - Dec 12
Love Ridge Mountain Lodging
Standard Suite, 1 Queen Bed | Living area | LCD TV, DVD player
Affordable Suites of America Waynesboro

Apartment in Waynesboro

2.5 star property
9.4 out of 10, Exceptional, (53)
"Always a pleasant stay."
United States
MARJORIE
The price is NT$2,588
NT$2,881 total
includes taxes & fees
Jan 2 - 2026/1/3
Affordable Suites of America Waynesboro
Apartment | 4 bedrooms
Stoney Creek Cottage Wintergreen w EV Charger

Apartment in Nellysford

2.0 star property
The price is NT$4,147
NT$12,952 total
includes taxes & fees
Dec 11 - Dec 12
Stoney Creek Cottage Wintergreen w EV Charger
Interior detail
Afton Mountain Vineyards

Cabin in Afton

2.5 star property
10.0 out of 10, Exceptional, (1)
"Amazing little cottage with everything you need. Loved the back porch and listening to music from the winery and enjoying the view. Good news, did not hear the music inside. "
United States
Kristin
The price is NT$10,914
NT$12,256 total
includes taxes & fees
Dec 11 - Dec 12
Afton Mountain Vineyards
House (3 Bedrooms) | Interior
Modern Nellysford Getaway on 40 Private Acres!

Cottage in Nellysford

3.0 star property
The price is NT$7,640
NT$18,967 total
includes taxes & fees
Dec 24 - Dec 25
Modern Nellysford Getaway on 40 Private Acres!
Apartment, Private Bathroom (The Serendipity Suite) | Exterior
The Serendipity Suite

Apartment in Staunton

2.0 star property
10.0 out of 10, Exceptional, (6)
"Cute and tidy. Easy check in and out. Easy parking and walk to dining. EV charge is for teslas, you'll need an adapter."
United States
Jennifer
The price is NT$2,775
NT$4,979 total
includes taxes & fees
Dec 11 - Dec 12
The Serendipity Suite
Apartment, Private Bathroom (The Urban Cowboy) | Exterior
The Urban Cowboy

Apartment in Staunton

2.0 star property
8.6 out of 10, Excellent, (7)
"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 NT$2,775
NT$4,979 total
includes taxes & fees
Dec 11 - Dec 12
The Urban Cowboy
Luxury Room, Ensuite (The Storefront) | Bar (on property)
The Storefront

Townhouse in Staunton

3.5 star property
8.8 out of 10, Excellent, (58)
"Great place to stay in charming Staunton!"
United States
Kate
The price is NT$4,646
NT$7,075 total
includes taxes & fees
Dec 14 - Dec 15
The Storefront
Apartment, Private Bathroom (The Shenandoah Suite) | Exterior
The Shenandoah Suite

Apartment in Staunton

2.0 star property
10.0 out of 10, Exceptional, (5)
"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 NT$2,775
NT$4,979 total
includes taxes & fees
Dec 14 - Dec 15
The Shenandoah Suite
Apartment, Private Bathroom (North Central Loft) | Exterior
North Central Loft

Apartment in Staunton

2.0 star property
10.0 out of 10, Exceptional, (3)
"Clean, comfortable, fun, well appointed and thoughtful details. A great place. "
United States
Stacey
The price is NT$5,613
NT$11,743 total
includes taxes & fees
Jan 5 - 2026/1/6
North Central Loft
Apartment, Private Bathroom (The Bons Amis Suite) | Lounge
The Bons Amis Suite

Apartment in Staunton

2.0 star property
9.4 out of 10, Exceptional, (3)
"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 NT$2,775
NT$4,979 total
includes taxes & fees
Jan 6 - 2026/1/7
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
  • 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 vacation rentals in Wintergreen?

Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip.

How many vacation rentals are there in Wintergreen?

Choose from 229 Expedia vacation rentals in Wintergreen for a memorable vacation.

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 vacation rental in Wintergreen like?

A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.