Photo by Rebecca Brent

Holiday Rentals in Wintergreen

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Holiday Rentals in Wintergreen

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

10.0 out of 10, Exceptional, (233)
"Clean, well maintained, phenomenal views. Comfy beds, lots of blankets, and pillows. We will definitely book again!"
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

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

9.6 out of 10, Exceptional, (300)
"Exactly as advertised. Clean, everything worked, great location."
The price is €370
includes taxes & fees
13 Apr - 14 Apr
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, (311)
"Fully equipped condo"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

10.0 out of 10, Exceptional, (132)
"My family and I stayed here for a long weekend to make the most of some local hikes, end of season snow on the slopes and quality time together. The property met all of our needs and wants when we were browsing for availabilities. We had a hiccup accessing the property during initial check in (key code) but the property owners were helpful and got us in quickly. Their responsiveness eased my concerns right from the start, should we have needed them for anything else during our stay.What stood...
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, (174)
"Nice property and views. "
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

Luxury Chalet, Best Views in Virginia

9.8 out of 10, Exceptional, (28)
"Quiet neighborhood with a heavenly view. It snowed while we were there, and the area roads management was impressive.Property is reasonably well-appointed. Perhaps geared more toward an adult party venue, we did find family-oriented supplies limited. Bring your own games, books. I would not recommend this property for families with young children for obvious reasons. The price of the view is a higher risk of slip/falls on the back incline, especially in snow.This rental is a special blessing...
Luxury Chalet, Best Views in Virginia

Blue Ridge Mountain Retreat in Wintergreen

9.2 out of 10, Wonderful, (64)
"Enjoyed our 2nd year here. Lots of room and fabulous kitchen. "
Blue Ridge Mountain Retreat in Wintergreen

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

9.0 out of 10, Wonderful, (269)
"Property was in a great location!"
The price is €228
includes taxes & fees
10 Apr - 11 Apr
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (177)
"We were greeted wonderfully by the manager. He was very helpful with places to go for lunch in the area & how to get there. The most pleasant ever encountered at a hotel. The rooms were great! Very clean & comfortable. Only problem experienced was the guests above us knocking around & playing their tv loud well after 10 p.m."
The price is €116
includes taxes & fees
13 Apr - 14 Apr
Valley Extended Suites

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (45)
"We were in the area to visit both colleges and Shenandoah National Park. The location made it the perfect place to do both. The cottage is charming with modern updates and unique little features that made it easy to relax. The owners were very quick to respond to our questions and made us feel incredibly welcome."
The price is €336
includes taxes & fees
10 Apr - 11 Apr
Ivy Rose Cottage nestled b/t Cville & Vineyards

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (70)
"We went to DC for our daughter's spring break and decided to add on a few days in the mountains. We picked this place based on the views we saw on the listing. I have to say those pictures do not do justice to the real views. We woke up before sunrise every day to make sure we could see them, absolutely breathtaking. The unit itself was very comfortable and well stocked. The hosts were extremely responsive to all of our questions and provided a guide with places to eat, drink and see.The pizza...
The price is €336
includes taxes & fees
11 Apr - 12 Apr
Endless Mountain Top Views from All The Way Up!

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

10.0 out of 10, Exceptional, (238)
"We travelled to Va to visit Monticello, wineries and breweries for my husband's 60th birthday with 3 other couples. The house was about 20minutes from Monticello and Jefferson winery so it was a perfect location for us. We absolutely loved the farm and the house. We got to see the baby goats which were so cute! We loved everything about our trip and the house was perfect for all of us. Thank you for a wonderful time! We would highly recommend staying here!Lisa Lawton"
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Afton Mountain Vineyards

2.0 star property
The price is €346
includes taxes & fees
10 Apr - 11 Apr
Afton Mountain Vineyards

Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.

10.0 out of 10, Exceptional, (101)
"My wife and I found the rental very well equipped and very clean and cozy. The artwork within the rental was way beyond standard and tasteful. The one bedroom with the single window had room darkening cellular shade and made it very dark which is great for a solid night sleep. I do wish it was a queen bed instead of a full size, but we managed. The tv selection for entertainment was good and better than most. Overall, highly recommended. La our guest was very kind and recommended different...
The price is €190
includes taxes & fees
10 Apr - 11 Apr
Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.

Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

10.0 out of 10, Exceptional, (38)
"Really cool property on the Piney River. Great fly fishing in the back yard. Tons of outdoor space- house itself is beautiful. Kids enjoyed their spring break hanging outside and fishing. "
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

10.0 out of 10, Exceptional, (61)
"What a beautiful view and location! We appreciated the details Della shared prior to our arrival and made navigating our weekend getaway super simple and enjoyable! Beautiful view! "
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!

10.0 out of 10, Exceptional, (34)
"Wow! Upon pulling up we were amazed with the location but as soon as we entered the front door, it was absolutely stunning! The cabin itself is SO CLEAN!!! We enjoyed sitting out on the large deck enjoying the view. There is a walking path that is cleared that we enjoyed as well! The host John was wonderful and we will definitely be back!! If I could give more STARS I would!"
The price is €259
includes taxes & fees
27 Apr - 28 Apr
New Cabin Right on The Rockfish River! Peacefull River Sounds, Stunning views!

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

10.0 out of 10, Exceptional, (15)
"the cabins are closer together than we expected but we were the only ones there that weekend, had a lovely time sitting by the fire listening the the creek"
The price is €210
includes taxes & fees
13 Apr - 14 Apr
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Wintergreen Resort Post & Beam Home Beauty

9.8 out of 10, Exceptional, (18)
"Terrific, well appointed, every thing we needed. "
Wintergreen Resort Post & Beam Home Beauty

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

10.0 out of 10, Exceptional, (24)
"Enjoyed our stay. The sunrises and sunsets were great. House was fun. Don’t miss visiting the dairy farm across the street. Lovely. Perfect place for a relaxing time. "
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
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, (300)
"Exactly as advertised. Clean, everything worked, great location."
The price is €370
includes taxes & fees
13 Apr - 14 Apr
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

10.0 out of 10, Exceptional, (233)
"Clean, well maintained, phenomenal views. Comfy beds, lots of blankets, and pillows. We will definitely book again!"
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

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

10.0 out of 10, Exceptional, (311)
"Fully equipped condo"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
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 Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub! and Blue Ridge Mountain Retreat in Wintergreen.

How many holiday rentals are there in Wintergreen?

Choose from 46 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.