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Wintergreen Vacation Rentals

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Vacation 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 CA $210
CA $536 total
includes taxes & fees
Apr 13 - Apr 14
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, (312)
"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, (270)
"Property was in a great location!"
The price is CA $120
CA $307 total
includes taxes & fees
Apr 16 - Apr 17
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 CA $139
CA $155 total
includes taxes & fees
Apr 13 - Apr 14
Valley Extended Suites

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (46)
"We very much enjoyed our stay. It is a great house that just feels good, even with some quirks. The gardens and yards are beautiful. The location is really nice too. Lots of close by hiking and events. The owners are great to talk to also!"
The price is CA $276
CA $493 total
includes taxes & fees
Apr 20 - Apr 21
Ivy Rose Cottage nestled b/t Cville & Vineyards

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (70)
"Lovely place with beautiful views!"
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 CA $468
CA $526 total
includes taxes & fees
Apr 13 - Apr 14
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 CA $153
CA $284 total
includes taxes & fees
Apr 13 - Apr 14
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 CA $305
CA $385 total
includes taxes & fees
Apr 27 - Apr 28
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, (16)
"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 CA $201
CA $313 total
includes taxes & fees
Apr 16 - Apr 17
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 CA $210
CA $536 total
includes taxes & fees
Apr 13 - Apr 14
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, (312)
"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 vacation rentals in Wintergreen?

Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip.

What are some of the best vacation rentals that Wintergreen has to offer?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: Visitors give good reviews to this Wintergreen vacation home rental, which is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation. Some other top choices in Wintergreen are Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub! and Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!.

How many vacation rentals are there in Wintergreen?

Choose from 47 Expedia vacation rentals in Wintergreen for a memorable vacation.

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 larger area.

What’s a vacation rental in Wintergreen like?

A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.