Photo by Rebecca Brent

Wintergreen Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Wintergreen holiday rentals

Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
The price is HK$741
HK$2,177 total
includes taxes & fees
21 Jan - 22 Jan
Laurelwood Hollow: Walk to Ski & Swim
Fireplace

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (39 reviews)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is HK$952
HK$2,111 total
includes taxes & fees
3 Feb - 4 Feb
The Modern Mountain Condo
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$1,942
HK$3,740 total
includes taxes & fees
20 Jan - 21 Jan
Blackwood Chalet
Fridge, microwave, oven, stovetop

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
2.0 star property
Wintergreen Resort
10.0 out of 10, Exceptional, (28 reviews)
"The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. "
United States
Cassie H.
The price is HK$965
HK$2,642 total
includes taxes & fees
19 Jan - 20 Jan
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Fridge, microwave, oven, stovetop

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
2.0 star property
Wintergreen Resort
9.8 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is HK$936
HK$2,408 total
includes taxes & fees
21 Jan - 22 Jan
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Exterior

Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen. Sunset Vista Villa - Close to the ski slopes
Wintergreen Resort
10.0 out of 10, Exceptional, (95 reviews)
"Fantastic stay again! Condo is perfect for a get away! "
United States
Jenna M.
The price is HK$1,298
HK$2,570 total
includes taxes & fees
19 Jan - 20 Jan
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Property grounds

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (145 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is HK$951
HK$2,067 total
includes taxes & fees
25 Jan - 26 Jan
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Terrace/patio

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Nellysford
10.0 out of 10, Exceptional, (24 reviews)
"The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. "
United States
Jody W.
The price is HK$1,474
HK$3,643 total
includes taxes & fees
21 Jan - 22 Jan
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Property grounds

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
2.0 star property
Wintergreen Resort
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is HK$819
HK$1,935 total
includes taxes & fees
3 Feb - 4 Feb
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (307 reviews)
"Outstanding views from the deck!! Loved it!"
United States
Kerry M.
The price is HK$807
HK$1,887 total
includes taxes & fees
19 Jan - 20 Jan
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Interior

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (25 reviews)
"Great communication from the startReturn texts the same day on any questionsGreat location for our tripVery cleanViews around property are greatNice restaurant A plus for what we neededDog friendly Thanks againHope to be back"
United States
Phil P.
The price is HK$936
HK$1,961 total
includes taxes & fees
19 Jan - 20 Jan
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Exterior

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (25 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is HK$1,027
HK$2,826 total
includes taxes & fees
20 Jan - 21 Jan
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Property grounds

Spacious 3BR 3BA Pet Friendly Resort Condo

Spacious 3BR 3BA Pet Friendly Resort Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (3 reviews)
"Awesome just Awesome place. Definitely recommend this place. Very well taken care of and everything you needed all rolled into one place. Thank you so much again and we will definitely be coming back. "
United States
Lance B.
The price is HK$1,817
HK$3,835 total
includes taxes & fees
21 Jan - 22 Jan
Spacious 3BR 3BA Pet Friendly Resort Condo
Exterior detail

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
Wintergreen Resort
10.0 out of 10, Exceptional, (40 reviews)
"Amazing stay! Space was clean, well stocked and easy to enter. Host was very responsive and gave lots of helpful information. Would recommend and stay again!"
United States
Sonja S.
The price is HK$891
HK$2,095 total
includes taxes & fees
20 Jan - 21 Jan
Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
Property grounds

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (92 reviews)
"Perfect location for our weekend stay! Close to trails and breweries and gorgeous views. Responsive hosts, clean and cozy condo. "
United States
Cari B.
The price is HK$2,510
HK$4,281 total
includes taxes & fees
6 Feb - 7 Feb
Endless Mountain Top Views from All The Way Up!
Outdoor spa tub

Bear Tracks Cottage: New Hot Tub + Fire Pit

Bear Tracks Cottage: New Hot Tub + Fire Pit
Nellysford
10.0 out of 10, Exceptional, (31 reviews)
"Perfect location for a golf trip to Stoney Creek Golf Club!"
United States
Randy R.
The price is HK$1,474
HK$3,441 total
includes taxes & fees
21 Jan - 22 Jan
Bear Tracks Cottage: New Hot Tub + Fire Pit
Smart TV, fireplace, books

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (49 reviews)
"Amazing stay for nelson 151 trip for Birthday. Owners are amazing communication was easy and quick. Property is beautiful and very well maintained. We will be staying here again. "
United States
DANIEL H.
Spacious + Serene Mtn Top Escape, 4 En Suites
Outdoor dining

5 Min to Ski, Mtn Views, Shuffleboard, Arcade Fun

5 Min to Ski, Mtn Views, Shuffleboard, Arcade Fun
2.0 star property
Chestnut Springs
10.0 out of 10, Exceptional, (1 review)
"The hosts thought of everything! We loved the house and would love to visit again. Thank you!"
United States
Anonymous traveller
The price is HK$1,461
HK$3,494 total
includes taxes & fees
20 Jan - 21 Jan
5 Min to Ski, Mtn Views, Shuffleboard, Arcade Fun
TV, fireplace

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.4 out of 10, Exceptional, (9 reviews)
"Beautiful view!"
United States
Serge L.
The price is HK$1,084
HK$2,286 total
includes taxes & fees
2 Feb - 3 Feb
Mountain View Vista: Resort Condo w/ Views
Smart TV

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (4 reviews)
"Great house and great host!"
United States
Joe B.
The price is HK$858
HK$2,855 total
includes taxes & fees
19 Jan - 20 Jan
Serenity Cabin-Woodland Retreat
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

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

10/10 Excellent
"Great location, beautiful view, responsive host! This was our third time staying. "
Megan S. 2-night trip
Posted 4 days ago
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

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?

2min to Ski Hot Tub EV Charger Mountain View DogOK: This highly rated holiday home rental in Wintergreen is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Wintergreen are Upscale and Family-Friendly in Wintergreen and Unbeatable Views Atop Wintergreen Resort.

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.