Photo by Rebecca Brent

Wintergreen Holiday Rentals

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Holiday Rentals in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (293)
"Cozy, Clean and Convenient!"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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

10.0 out of 10, Exceptional, (309)
"Clean, cozy,and convenient!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Condo -Steps to Ski and restaurants

9.8 out of 10, Exceptional, (9)
"Best price and a perfect little condo just a short walk to the ski lifts. An old man, 3 teenagers, and my mini me, truly enjoyed it. It has all you need to cook and chill out after a long day on the slopes. The fireplace with a constant supply of wood was the sugar on top. Thanks for a great stay."
The price is AU$384
includes taxes & fees
25 Feb - 26 Feb
Wintergreen Condo -Steps to Ski and restaurants

Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!

10.0 out of 10, Exceptional, (231)
"Absolutely loved my second stay at the gorgeous property! The sunrise and sunset views can’t be beat. "
Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!

The Modern Mountain Condo

10.0 out of 10, Exceptional, (20)
"Everything was good. Could not get the tv in bedroom to work. Would like to have a Keurig type coffee maker"
The price is AU$354
includes taxes & fees
24 Feb - 25 Feb
The Modern Mountain Condo

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

10.0 out of 10, Exceptional, (128)
"Beautiful accommodations. Every little thing was thought of. Fully stocked kitchen, night lights for every room in the house, gas fireplace, loved the hot tub, dog bags (we brought some, but it was great that if we forgot, they were provided), loved the mudroom. I have nothing negative to say."
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

9.8 out of 10, Exceptional, (173)
"Excellent stay overall. Weather kept us from enjoying the outside much but the cozy fireplace inside was super nice, especially with the supplied wood. Furniture was comfy and the smart TVs and streaming/cable was fabulous! "
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

9.4 out of 10, Exceptional, (81)
"Beautiful area and beautiful home."
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

Blue Ridge Mountain Retreat in Wintergreen

9.2 out of 10, Wonderful, (62)
"We had an amazing time staying at Wintergreen. Ashley was super easy to work with and the home was very accommodating! Everything was clean, spacious, with everything we needed. There was plenty of fire wood. We look forward to returning! "
Blue Ridge Mountain Retreat in Wintergreen

Large and Luxurious Exec 5BR Chalet

10.0 out of 10, Exceptional, (244)
"2 Families of 5 stayed here comfortably and it was excellent. Skiing entrance is a little bit of a walk but our 12 ,15 and 18 year olds did it no problem. "
Large and Luxurious Exec 5BR Chalet

Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

10.0 out of 10, Exceptional, (48)
"We just left this morning, and we are already planning our next stay. This place was absolutely PERFECT. It had every amenity we could ever need, especially the kitchen. The hot tub was exactly what we "
The price is AU$1,144
includes taxes & fees
2 Mar - 3 Mar
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

Ski-In/Ski-Out Comfy Condo

10.0 out of 10, Exceptional, (21)
"Great place with ski-in ski-out access! Well appointed and photos are accurate. Host was great! We would definitely stay again. "
Ski-In/Ski-Out Comfy Condo

Wintergreen Resort Getaway w/ Deck, Mountain View!

8.8 out of 10, Excellent, (8)
"We really enjoyed our stay at this charming home! The house was immaculately clean, spacious, and so well-equipped—it truly felt like home away from home.The views from the back deck were amazing.We highly recommend this vacation home to anyone looking for a memorable time!"
Wintergreen Resort Getaway w/ Deck, Mountain View!

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

9.0 out of 10, Wonderful, (264)
"The location and view were much appreciated and accurate from the website. Communication with the host initially went well as I wondered how equipped the kitchen was. Be prepared to bring your own dishwashing liquid, laundry soap (washer not used), and preferred spices. We made dinner a couple of nights and it was well equipped. There was minimal hand soap and no additional trash bags. The kitchen stove had tomato food stains, and I ended up sweeping which didn't look done. I sent a couple of...
The price is AU$374
includes taxes & fees
19 Mar - 20 Mar
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (173)
"We have stayed here twice in the last two months. Both rooms were immaculately clean! Front office staff was pleasant and accommodating both times (It was the same woman both times...I just can't remember her name. ) If you are going to stay here, you so need to bring a hair dryer, conditioner (shampoo is provided), creamer( if you don't like French vanilla)"
The price is AU$186
includes taxes & fees
24 Feb - 25 Feb
Valley Extended Suites

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was very nicely set up, clean, and comfortable. The property manager was in constant contact with me to make sure I had everything I needed. I would highly recommend this place to anyone looking for a quiet relaxing escape. "
The price is AU$415
includes taxes & fees
24 Feb - 25 Feb
Love Ridge Mountain Lodging

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (38)
"We spent a fun girls weekend at the cottage. It’s exactly as described. Very cute and cozy. It was just far enough away from the bustle of the city but close enough that driving out to the heart of Charlottesville was only 20 mins away. The beds were comfortable and it had everything you needed. "
The price is AU$562
includes taxes & fees
19 Mar - 20 Mar
Ivy Rose Cottage nestled b/t Cville & Vineyards

RIGHT ON THE ROCKFISH RIVER!Brand New Cabin, Completely Private,Peaceful,Hiking!

10.0 out of 10, Exceptional, (32)
"We chose this property for a girls getaway, and it was exactly what we were looking for. The views were gorgeous even in January! It was easy to see the river from all bedrooms and the living and kitchen areas through big floor to ceiling windows. "
The price is AU$382
includes taxes & fees
20 Feb - 21 Feb
RIGHT ON THE ROCKFISH RIVER!Brand New Cabin, Completely Private,Peaceful,Hiking!

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

10.0 out of 10, Exceptional, (234)
"A beautiful historic property and working farm, it was the perfect getaway for some lifelong friends looking to get away. Bill and Cynthia are wonderful hosts and the home has everything you could need. It is very large and can easily accommodate a large family or group event.We were even given samples of maple water from the frees, and farm-fresh eggs! We would definitely stay here again.Thank you Bill and Cynthia for a perfect weekend."
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

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

9.4 out of 10, Exceptional, (120)
"Well stocked kitchen, , clean, firewood provided, close to mountain!! would come back again"
The price is AU$383
includes taxes & fees
20 Mar - 21 Mar
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
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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Other types of properties in Wintergreen you may be interested in

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (293)
"Cozy, Clean and Convenient!"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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

10.0 out of 10, Exceptional, (309)
"Clean, cozy,and convenient!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!

10.0 out of 10, Exceptional, (231)
"Absolutely loved my second stay at the gorgeous property! The sunrise and sunset views can’t be beat. "
Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!
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.

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?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: This highly rated holiday home rental in Wintergreen is located on a lake, 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 balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Some other top choices in Wintergreen are Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort! and Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK.

How many holiday rentals are there in Wintergreen?

Choose from 43 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. Wintergreen Resort and Bold Rock Hard Cider Nellysford Cidery are a couple of places you'll find in the wider area.

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.