Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

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 RM1,017
RM1,953 total
includes taxes & fees
27 Jan - 28 Jan
Blackwood Chalet
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 RM361
RM676 total
includes taxes & fees
28 Jan - 29 Jan
The Bohemian Suite
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 RM462
RM514 total
includes taxes & fees
25 Jan - 26 Jan
Valley Extended Suites
Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (16 reviews)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is RM503
RM808 total
includes taxes & fees
22 Jan - 23 Jan
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 RM1,418
RM1,593 total
includes taxes & fees
22 Jan - 23 Jan
Afton Mountain Vineyards
4 bedrooms

Waynesboro Home Near Wintergreen Charlottesville

Waynesboro Home Near Wintergreen Charlottesville
2.0 star property
Waynesboro
The price is RM1,026
RM2,836 total
includes taxes & fees
22 Jan - 23 Jan
Waynesboro Home Near Wintergreen Charlottesville
Exterior

The Shenandoah Suite

The Shenandoah Suite
2.0 star property
Staunton
10.0 out of 10, Exceptional, (5 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 RM361
RM676 total
includes taxes & fees
22 Jan - 23 Jan
The Shenandoah Suite
Lounge

The Storefront

The Storefront
3.5 star property
Staunton
8.8 out of 10, Excellent, (58 reviews)
"Great place to stay in charming Staunton!"
United States
Kate
The price is RM604
RM919 total
includes taxes & fees
22 Jan - 23 Jan
The Storefront
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 RM729
RM1,526 total
includes taxes & fees
18 Feb - 19 Feb
North Central Loft
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 RM361
RM677 total
includes taxes & fees
26 Jan - 27 Jan
The Urban Cowboy
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 RM361
RM676 total
includes taxes & fees
29 Jan - 30 Jan
The Serendipity Suite
Exterior

The Bons Amis Suite

The Bons Amis Suite
2.0 star property
Staunton
9.4 out of 10, Exceptional, (3 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 RM361
RM676 total
includes taxes & fees
2 Feb - 3 Feb
The Bons Amis Suite
Private kitchen

Fishersville Oasis

Fishersville Oasis
2.0 star property
Fishersville
The price is RM401
RM785 total
includes taxes & fees
3 Feb - 4 Feb
Fishersville Oasis
4 bedrooms

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is RM770
RM2,057 total
includes taxes & fees
22 Jan - 23 Jan
Stoney Creek Cottage Wintergreen w EV Charger
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 230 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.