Wintergreen Holiday Rentals

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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 Sept - 27 Sept

Our top choices for Wintergreen holiday rentals

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 HK$956
HK$2,662 total
includes taxes & fees
7 Jun - 8 Jun
Wintergreen Ski Resort Condo w/ Golf Access!
Exterior

Laurelwood Hollow

Laurelwood Hollow
2.0 star property
Nellysford
The price is HK$744
HK$2,012 total
includes taxes & fees
4 Jun - 5 Jun
Laurelwood Hollow
Room

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is HK$1,959
HK$3,961 total
includes taxes & fees
3 Jun - 4 Jun
Mountain Mindset
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 HK$1,325
HK$3,248 total
includes taxes & fees
7 Jun - 8 Jun
Blackwood Chalet
Private kitchen

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 HK$650
HK$724 total
includes taxes & fees
8 Jun - 9 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 HK$893
HK$994 total
includes taxes & fees
7 Jun - 8 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 HK$3,058
HK$3,434 total
includes taxes & fees
9 Jun - 10 Jun
Afton Mountain Vineyards
Room

Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is HK$901
HK$2,112 total
includes taxes & fees
3 Jun - 4 Jun
Bluebird Cottage
4 bedrooms

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
Nellysford
The price is HK$1,766
HK$3,936 total
includes taxes & fees
3 Jun - 4 Jun
Stoney Creek Cottage Wintergreen w EV Charger
Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is HK$1,920
HK$4,767 total
includes taxes & fees
16 Jun - 17 Jun
Modern Nellysford Getaway on 40 Private Acres!
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 HK$1,099
HK$1,704 total
includes taxes & fees
8 Jun - 9 Jun
Love Ridge Mountain Lodging
Dining

Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
Tucked Inn: Upper Unit
Exterior

Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is HK$2,343
HK$4,983 total
includes taxes & fees
3 Jun - 4 Jun
Branch and Barrel
Interior

Magnolia Suite

Magnolia Suite
2.0 star property
Staunton
The price is HK$807
HK$1,492 total
includes taxes & fees
15 Jun - 16 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

Where the Trail Ends

Where the Trail Ends

10/10 Excellent
"Very nice condo. Great location. Clean. Comfortable."
Aline L. 1-night trip
Posted 3 days ago
Where the Trail Ends

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 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.

What are some of the best holiday rentals that Wintergreen has to offer?

One of the Best Views in Wintergreen!: This highly rated holiday home rental in Wintergreen is located in the mountains, and has an indoor pool, a fireplace and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a patio and an outdoor tennis court. Some other top choices in Wintergreen are Heaven On Earth ~ Wintergreen Mountain and Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!.

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.