Wintergreen Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Wintergreen holiday rentals

Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (33 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is HK$893
HK$2,076 total
includes taxes & fees
23 Apr - 24 Apr
Wintergreen Condo -Steps to Ski and restaurants
1 bedroom, desk, Internet, bed sheets

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.8 out of 10, Exceptional, (42 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
The price is HK$1,088
HK$2,276 total
includes taxes & fees
22 Apr - 23 Apr
Panoramic Peak: Wintergreen Condo with Views
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, (151 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is HK$861
HK$1,889 total
includes taxes & fees
22 Apr - 23 Apr
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
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, (101 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
Endless Mountain Top Views from All The Way Up!
Fridge, microwave, oven, stovetop

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

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"Cozy, clean very attentive host Paul was amazingThis cozy kid friendly family home was very accommodating. Def will be back again!!"
United States
Pamela P.
The price is HK$810
HK$2,421 total
includes taxes & fees
22 Apr - 23 Apr
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Exterior

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

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (31 reviews)
"Well stocked house with great layout for families or two couples. Great kitchen setup with everything you’ll need. Close to the resort and skiing. Close to hiking trails. "
United States
Jeremiah H.
The price is HK$846
HK$2,507 total
includes taxes & fees
29 Apr - 30 Apr
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Fridge, microwave, oven, stovetop

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

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is HK$1,056
HK$2,513 total
includes taxes & fees
20 Apr - 21 Apr
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Exterior

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (107 reviews)
"Very nice, updated place with everything we needed. We would definitely stay here again!"
United States
Kimberly M.
The price is HK$1,409
HK$2,698 total
includes taxes & fees
1 May - 2 May
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
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, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is HK$939
HK$1,898 total
includes taxes & fees
30 Apr - 1 May
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
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
Wintergreen Resort
10.0 out of 10, Exceptional, (14 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$634
HK$1,678 total
includes taxes & fees
22 Apr - 23 Apr
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
TV, fireplace

Wintergreen Resort Condo Available Now!!

Wintergreen Resort Condo Available Now!!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
The price is HK$1,213
HK$2,534 total
includes taxes & fees
19 Apr - 20 Apr
Wintergreen Resort Condo Available Now!!

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, (317 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is HK$810
HK$1,920 total
includes taxes & fees
28 Apr - 29 Apr
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Outdoor dining

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (126 reviews)
"Everything was as is listed, we were off season so hiking and scenic views is what there was to do, relaxing. Host was accessible on phone, place was clean. "
United States
David L.
The price is HK$909
HK$2,022 total
includes taxes & fees
27 Apr - 28 Apr
Escape to the Blue Ridge Mountains at Wine-tergreen!
Fireplace

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (48 reviews)
"Great place to stay to hit the ski slopes. Just a short walk to the slopes and right next to the gas station/ small grocery shop to easily pick up some food on the way back from skiing. "
United States
Joyce B.
The price is HK$738
HK$1,795 total
includes taxes & fees
21 Apr - 22 Apr
The Modern Mountain Condo
Exterior

Mountain Inn Studio 94 with Wintergreen Advantage

Mountain Inn Studio 94 with Wintergreen Advantage
Wintergreen
The price is HK$1,011
HK$1,785 total
includes taxes & fees
19 Apr - 20 Apr
Mountain Inn Studio 94 with Wintergreen Advantage
Fridge, microwave, oven, stovetop

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (38 reviews)
"Amazing spot! Ski in - out was so convenient and a quick walk to the village! Phyllis was amazing and the condo was beautiful! Would definitely book this condo again! "
United States
Susan J.
The price is HK$1,189
HK$3,200 total
includes taxes & fees
19 Apr - 20 Apr
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Exterior

Three Ridges 64 With Wintergreen Advantage

Three Ridges 64 With Wintergreen Advantage
Chestnut Springs
The price is HK$1,283
HK$2,341 total
includes taxes & fees
18 Apr - 19 Apr
Three Ridges 64 With Wintergreen Advantage
Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 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$744
HK$2,187 total
includes taxes & fees
11 May - 12 May
Laurelwood Hollow: Walk to Ski & Swim
Smart TV

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (12 reviews)
"Great house and great host!"
United States
Joe B.
The price is HK$904
HK$2,946 total
includes taxes & fees
20 Apr - 21 Apr
Serenity Cabin-Woodland Retreat
TV, fireplace

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful condo"
United States
Mary C.
The price is HK$1,088
HK$2,294 total
includes taxes & fees
19 Apr - 20 Apr
Mountain View Vista: Resort Condo w/ Views
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

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

10/10 Excellent
"Amazing view, comfy beds, terrific place for a getaway !"
Carmela S. 3-night trip
Posted 22 hours ago
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

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
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  • 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?

Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope: This highly rated holiday home rental in Wintergreen is located in the mountains, and has a patio, a selection of games 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. Some other top choices in Wintergreen are Upscale and Family-Friendly in Wintergreen and Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14.

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.