Wintergreen Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Wintergreen holiday rentals

Exterior

Condo in Wintergreen Resort

Wintergreen. Sunset Vista Villa - Close to the ski slopes
10.0 out of 10, Exceptional, (104 reviews)
"We had a great time! The host was very responsive and great location! "
United States
Tess B.
The price is HK$845
HK$1,916 total
includes taxes & fees
19 Mar - 20 Mar
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Exterior

Condo in Wintergreen

Overlook 08 with Wintergreen Advantage
Overlook 08 with Wintergreen Advantage
Exterior

Condo in Wintergreen

Tanners Ridge 21 with Wintergreen Advantage
The price is HK$1,636
HK$2,935 total
includes taxes & fees
19 Mar - 20 Mar
Tanners Ridge 21 with Wintergreen Advantage
Property grounds

Condo in Wintergreen Resort

Endless Mountain Top Views from All The Way Up!
10.0 out of 10, Exceptional, (98 reviews)
"Highly recommend staying at this beautiful condo! The kitchen has everything you need, the views are breath-taking, the condo is very clean, and the hosts are very communicative and helpful. Will definitely stay here again the next time we travel to the area!"
United States
Allison N.
The price is HK$731
HK$2,008 total
includes taxes & fees
18 Mar - 19 Mar
Endless Mountain Top Views from All The Way Up!
Exterior

Condo in Wintergreen

Fairway Woods 01 with Wintergreen Advantage
Fairway Woods 01 with Wintergreen Advantage
Terrace/patio

Condo in Wintergreen Resort

Wintergreen Condo -Steps to Ski and restaurants
9.8 out of 10, Exceptional, (31 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is HK$892
HK$2,075 total
includes taxes & fees
18 Mar - 19 Mar
Wintergreen Condo -Steps to Ski and restaurants
Fridge, microwave, oven, stovetop

Condo in Wintergreen Resort

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
10.0 out of 10, Exceptional, (34 reviews)
"Great"
United States
Daniel W.
The price is HK$1,112
HK$3,081 total
includes taxes & fees
18 Mar - 19 Mar
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Property grounds

Condo in Roseland

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
9.6 out of 10, Exceptional, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is HK$861
HK$1,890 total
includes taxes & fees
18 Mar - 19 Mar
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Fridge, microwave, oven, stovetop

Condo in Wintergreen Resort

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
10.0 out of 10, Exceptional, (34 reviews)
"The home was clean and in a great location to explore the Wintergreen area. Host was welcoming and responsive."
United States
Rob M.
The price is HK$916
HK$2,541 total
includes taxes & fees
18 Mar - 19 Mar
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Property grounds

Condo in Wintergreen Resort

Escape to the Blue Ridge Mountains at Wine-tergreen!
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$2,014 total
includes taxes & fees
18 Mar - 19 Mar
Escape to the Blue Ridge Mountains at Wine-tergreen!
Fridge, microwave, oven, stovetop

Condo in Wintergreen Resort

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
9.4 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is HK$1,174
HK$2,637 total
includes taxes & fees
29 Mar - 30 Mar
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Front of property

Apartment in Nellysford

Wintergreen Ski Resort Condo w/ Golf Access!
4.0 star property
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$955
HK$2,659 total
includes taxes & fees
18 Mar - 19 Mar
Wintergreen Ski Resort Condo w/ Golf Access!
Exterior

Apartment in Wintergreen Resort

Laurelwood Hollow: Walk to Ski & Swim
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$2,185 total
includes taxes & fees
22 Mar - 23 Mar
Laurelwood Hollow: Walk to Ski & Swim
Property grounds

Condo in Roseland

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (316 reviews)
"Gorgeous view. Our fourth time here, and still a lovely place. "
United States
Elaine B.
The price is HK$810
HK$1,930 total
includes taxes & fees
18 Mar - 19 Mar
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Property grounds

Condo in Wintergreen Resort

Luxury Condo in the Sky! Finest in Wintergreen!
10.0 out of 10, Exceptional, (27 reviews)
"Amazing place with even more amazing views. Very comfortable and beautiful place. We had high expectations based on the pictures in the listing, and the place exceeded these high expectations. Fantastic place."
United States
missy s.
The price is HK$1,065
HK$2,427 total
includes taxes & fees
18 Mar - 19 Mar
Luxury Condo in the Sky! Finest in Wintergreen!
Smart TV, fireplace, ping pong, books

Holiday Home in Chestnut Springs

4 BR cabin mins to trails & breweries pets welcome
9.4 out of 10, Exceptional, (33 reviews)
"Nice place and very clean "
United States
Melad K.
The price is HK$1,515
HK$4,567 total
includes taxes & fees
18 Mar - 19 Mar
4 BR cabin mins to trails & breweries pets welcome
1 bedroom, desk, Internet, bed sheets

Condo in Wintergreen Resort

Panoramic Peak: Wintergreen Condo with Views
9.6 out of 10, Exceptional, (40 reviews)
"Very clean, well organized, excellent views"
United States
Guy M.
The price is HK$1,088
HK$2,259 total
includes taxes & fees
18 Mar - 19 Mar
Panoramic Peak: Wintergreen Condo with Views
Interior

Condo in Roseland

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
9.8 out of 10, Exceptional, (30 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$939
HK$1,899 total
includes taxes & fees
18 Mar - 19 Mar
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Fridge, microwave, oven, stovetop

Holiday Home in Chestnut Springs

Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin
10.0 out of 10, Exceptional, (16 reviews)
"Perfect spot for a family retreat - highly recommend "
United States
Greg B.
The price is HK$2,069
HK$4,583 total
includes taxes & fees
18 Mar - 19 Mar
Hike. Soak. Play. - Hot Tub, Sauna, Fire Pit & Game-Filled Fam Friendly Cabin
Exterior

Condo in Wintergreen

Stoneridge Woods 05 with Wintergreen Advantage
10.0 out of 10, Exceptional, (1 review)
"Loved the house. The layout was great and worked great for our family."
United States
Torry M.
Stoneridge Woods 05 with Wintergreen Advantage
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 Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10/10 Excellent
"We had a wonderful time! The condo was perfect for our family of 4 with 2 small dogs. The condo was clean, well laid out, and very well stocked. It had everything we needed and more! The communication with the host was super fast and helpful. We already booked for next year!"
Neal & Sarah W. 2-night trip
Posted 1 day ago
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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?

4 BR cabin mins to trails & breweries pets welcome: This highly rated holiday home rental in Wintergreen offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable 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. Make the most of games in this rental home to help you unwind. Some other top choices in Wintergreen are Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope and Insane Mountain Views - New Listing.

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.