Beautiful small lake surrounded with wintergreen forest. Dajicko lake on Golija Mountain in Serbia

Wintergreen Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Wintergreen holiday rentals

Exterior

Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is RM743
RM1,655 total
includes taxes & fees
29 Jun - 30 Jun
Bear Tracks Cottage
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 RM495
RM1,379 total
includes taxes & fees
15 Jun - 16 Jun
Wintergreen Ski Resort Condo w/ Golf Access!
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 RM688
RM1,686 total
includes taxes & fees
14 Jun - 15 Jun
Blackwood Chalet
Exterior

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is RM1,180
RM2,239 total
includes taxes & fees
14 Jun - 15 Jun
Mountain Mindset
Lounge

Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is RM732
RM1,394 total
includes taxes & fees
16 Jun - 17 Jun
Firefly on The Ridge
Exterior

Laurelwood Hollow

Laurelwood Hollow
2.0 star property
Nellysford
The price is RM386
RM1,042 total
includes taxes & fees
5 Jul - 6 Jul
Laurelwood Hollow
1 bedroom

Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
The price is RM564
RM1,044 total
includes taxes & fees
6 Jul - 7 Jul
Mountain View Vista
1 bedroom

Panoramic Peak

Panoramic Peak
2.0 star property
Nellysford
The price is RM566
RM1,047 total
includes taxes & fees
17 Jun - 18 Jun
Panoramic Peak
5 bedrooms

Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
The price is RM1,827
RM3,651 total
includes taxes & fees
14 Jun - 15 Jun
Red White and Wintergreen
Private kitchen

Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.2 out of 10, Wonderful, (61 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is RM321
RM357 total
includes taxes & fees
14 Jun - 15 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, (242 reviews)
"Stay here 2 times a year, and doesn’t disappoint."
United States
Kate
The price is RM463
RM515 total
includes taxes & fees
16 Jun - 17 Jun
Valley Extended Suites
Exterior

Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is RM467
RM1,094 total
includes taxes & fees
24 Jun - 25 Jun
Bluebird Cottage
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 RM587
RM903 total
includes taxes & fees
15 Jun - 16 Jun
Love Ridge Mountain Lodging
Interior detail

Afton Mountain Vineyards

Afton Mountain Vineyards
3.0 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 RM1,584
RM1,779 total
includes taxes & fees
24 Jun - 25 Jun
Afton Mountain Vineyards
Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is RM995
RM2,470 total
includes taxes & fees
24 Jun - 25 Jun
Modern Nellysford Getaway on 40 Private Acres!
Exterior

Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is RM483
RM1,113 total
includes taxes & fees
24 Jun - 25 Jun
Artisan's Cottage
Exterior

Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is RM406
RM1,140 total
includes taxes & fees
14 Jun - 15 Jun
Tucked Inn: Lower Unit
Interior

The Farmhouse at Wellington

The Farmhouse at Wellington
2.0 star property
Waynesboro
The price is RM1,125
RM2,495 total
includes taxes & fees
15 Jun - 16 Jun
The Farmhouse at Wellington
Exterior

Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
The price is RM686
RM1,583 total
includes taxes & fees
16 Jun - 17 Jun
Little Haven Cottage
Terrace/patio

Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
The price is RM427
RM1,165 total
includes taxes & fees
17 Jun - 18 Jun
Tucked Inn: Upper Unit
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 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.