Wintergreen Vacation Rentals

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Check prices for these dates

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

Our top choices for Wintergreen vacation 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 P7,516
P20,923 total
includes taxes & fees
Jun 3 - Jun 4
Wintergreen Ski Resort Condo w/ Golf Access!
Exterior

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is P15,894
P31,685 total
includes taxes & fees
Jun 3 - Jun 4
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 P10,411
P25,528 total
includes taxes & fees
Jun 7 - Jun 8
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 P5,113
P5,691 total
includes taxes & fees
Jun 8 - Jun 9
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 P7,023
P7,816 total
includes taxes & fees
Jun 3 - Jun 4
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 P24,038
P26,994 total
includes taxes & fees
Jun 3 - Jun 4
Afton Mountain Vineyards
Room

Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is P7,084
P16,604 total
includes taxes & fees
Jun 3 - Jun 4
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 P14,471
P31,627 total
includes taxes & fees
Jun 3 - Jun 4
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 P15,093
P37,472 total
includes taxes & fees
Jun 16 - Jun 17
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 P8,640
P13,399 total
includes taxes & fees
Jun 3 - Jun 4
Love Ridge Mountain Lodging
Dining

Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
The price is P6,468
P17,642 total
includes taxes & fees
Jun 3 - Jun 4
Tucked Inn: Upper Unit
Exterior

Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is P18,420
P39,167 total
includes taxes & fees
Jun 3 - Jun 4
Branch and Barrel
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:

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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 223 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.