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Compare 279 Vacation Homes in Wingina with updated reviews, rates, and availability.

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Fresh Private Hot Tub Lower Deck Relaxing Location in woods with Beautiful Views
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
9.6 out of 10, Exceptional, (275)
"Stayed here with some friends on a quick golf trip and it was an ideal spot. The house is well-maintained and having 4 full sized beds worked out great. The host is an excellent communicator and was quick to answer any questions we had. "
The price is SAR 615
SAR 1,509 total
includes taxes & fees
24 Sep - 25 Sep
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
The newest and largest edition to the Wintergreen Retreat portfolio!
Living area
The newest and largest edition to the Wintergreen Retreat portfolio!
9.6 out of 10, Exceptional, (34)
"We couldn’t have had a better weekend! Our host was very easy to communicate with and the house was beautiful. Would highly recommend for large gatherings. Proximity to outlooks and outdoor activities can’t be beat!"
The newest and largest edition to the Wintergreen Retreat portfolio!
Peaceful Retreat w/ Hot Tub, Fire Pit, Mountain Views
7-person hot tub on rear deck
Peaceful Retreat w/ Hot Tub, Fire Pit, Mountain Views
10.0 out of 10, Exceptional, (9)
"This place was perfect! It's a really good location near the wineries and breweries. The house is really spacious with comfortable furniture. And while there are houses around this one is conveniently situated where you feel totally private when you walk out the back door. We really enjoyed the firepit, hot tub and the little walk to the creek."
The price is SAR 705
SAR 1,837 total
includes taxes & fees
30 Sep - 1 Oct
Peaceful Retreat w/ Hot Tub, Fire Pit, Mountain Views
Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen
View from one of two decks on upper level
Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen
10.0 out of 10, Exceptional, (113)
"Property was everything we were hoping for. The view was spectacular. We hope to return in the future. Vestal was very responsive. "
Renovated 5-BR Home with Unbeatable Views at the Top of Wintergreen
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!
Stone Patio, Adirondack Chairs, Fire Pit & Amazing Views of Mountains and Valley
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!
9.8 out of 10, Exceptional, (165)
"Wonderful property that fit the three families in our group very well, and amazing views! House well laid out and stocked, we had everything we needed. Beds super comfortable. Close proximity to local cideries and breweries, which was nice, but it was also great just staying on the property and enjoying those views. Especially loved the lower patio with the Adirondack chairs, perfect for gazing over the valley. Overall a great weekend getaway."
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Private kitchen
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
10.0 out of 10, Exceptional, (113)
"Place was convenient, well stocked, and homey. Management responded when something needed addressing. "
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries
Welcome to Elmwood Acres: an 1890's, 5BR/3.5BA farmhouse situated among hundreds of acres of pastures and orchards with jaw-dropping mountain views, a heated pool, hiking trails, huge yard, and several barns converted into a playhouse and man cave.
Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries
10.0 out of 10, Exceptional, (23)
"I, my wife, and 2 grandchildren had an absolutely grand time at the farmhouse. Older home that has been renovated to today's needs and wants was situated on a higher point offering great viewes day and night of the Blue Ridge mountains (could see muliple ridges). Pool was both relaxing and had plenty of floats, football and other items to keep us entertain. Speaking of entertainment the arcade in a rustic barn setting was so cool. Can't say enough about the property. For family or a group of...
Farmhouse getaway for family vacations and friend retreats - heated pool, amazing views, close to wineries/breweries
Spacious + Serene Mtn Top Escape, 4 En Suites
Main living floor contains dining, kitchen, living room, and half bath.
Spacious + Serene Mtn Top Escape, 4 En Suites
10.0 out of 10, Exceptional, (23)
"We loved everything: easy communication, clean, cosy, fully equipped house. Overall, a great place to spend a long weekend in Wintergreen. "
The price is SAR 616
SAR 1,745 total
includes taxes & fees
24 Sep - 25 Sep
Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Hot tub out back
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
10.0 out of 10, Exceptional, (38)
"This property was a great location for our family vacation. The place was very clean when we arrived, the best of any VRBO location we have enjoyed. The well stocked kitchen provided the necessary tools for our family meals. We enjoyed our time there, and the black bear that went by in the woods, was an added adventure."
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Luxe Wintergreen Resort Escape w/ Hot Tub!
Roseland Vacation Rental | 4BR | 3BA | Stairs Required | 3,174 Sq Ft
Luxe Wintergreen Resort Escape w/ Hot Tub!
10.0 out of 10, Exceptional, (16)
"The property was clean and fresh. The location is literally at the top of a mountain with beautiful views. We enjoyed our stay at this property."
Luxe Wintergreen Resort Escape w/ Hot Tub!
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
Living area
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
10.0 out of 10, Exceptional, (52)
"House very nice, clean and in good condition. Very comfortable, and we enjoyed our stay there. A few minor things needed some attention, and I discussed those with the property manager. We were without water for about 16 hours, apparently due to a water main break somewhere nearby. The property manager was very helpful and kept us well updated as to the progress in repairing it. Some of the decks and outside wooden stairs will need some attention, mainly paint, in the near future. "
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope
Enjoy a meal at the outdoor eating area with this mountain view as your backdrop
Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope
10.0 out of 10, Exceptional, (50)
"We thoroughly enjoyed our visit! The check in and check out process was very easy, the house was stunning, and views were absolutely beautiful. We were a five min drive from the main wintergreen entrance and a quick 15-20 min from all sorts of breweries, cideries and wineries. We really enjoyed the sunroom off of the main bedroom, the cozy living room and well appointed kitchen. Would definitely stay again!"
Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope
Get out of the city and enjoy the country life at the Buffalo River Bungalow
Exterior
Get out of the city and enjoy the country life at the Buffalo River Bungalow
9.8 out of 10, Exceptional, (36)
"Perfect for a getaway from the city!"
Get out of the city and enjoy the country life at the Buffalo River Bungalow
Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!
Exterior
Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!
10.0 out of 10, Exceptional, (1)
"- House is well taken care of. - House rule not wearing shoes inside and providing sleepers keeps the house clean. We liked it, but should mention that on VRBO listing. (It is listed on the competitors listing among the other info) Also, be better if the closed in shoes cabinet is available to protect the shoes from the weather. - Would be better if the property manager sent check-in info at least a day earlier than the middle of the day of check-in."
The price is SAR 1,876
SAR 3,852 total
includes taxes & fees
24 Sep - 25 Sep
Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!
Restored Double Log Cabin on 400 Mountain Acres
Great Room with sectional facing stone fireplace. Porch and Fire Pit outside.
Restored Double Log Cabin on 400 Mountain Acres
10.0 out of 10, Exceptional, (222)
"This cabin was perfect for an extended family vacation. The location is remote enough to enjoy some quiet time and enjoy the surroundings, but close enough to venture out for hiking, fishing, and beer/wine tasting. The bedrooms are well situated so we weren't on top of each other. The covered porch and rocking chairs were the best part of the house! "
Restored Double Log Cabin on 400 Mountain Acres
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
Exterior
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
9.8 out of 10, Exceptional, (60)
"I recently stayed here with my husband and our six kids. The house is beautiful, clean, and very cozy! The driveway is a bit intimidating but we got used to it fairly quickly. Overall it was a nice place and we would definitely stay here again."
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
Insane Mountain Views - New Listing
Main Floor Family Room
Insane Mountain Views - New Listing
10.0 out of 10, Exceptional, (20)
"This property was the perfect space for us as we celebrated my mom’s 80th birthday with my siblings and our kids. The layout of the home couldn’t have been better. The views and amenities were outstanding! We’re already talking about when we can come back! We had 5 kids, ages 11-16, and they were comfortably spread out in the 2 bedrooms in the basement. The primary bedroom on the main floor was perfect for my parents. The four upstairs bedrooms were ideal for my brothers and our spouses. I...
Insane Mountain Views - New Listing
Event Space for Families or Groups
Living area
Event Space for Families or Groups
10.0 out of 10, Exceptional, (25)
"We had a friends weekend and had a blast at the property. The house was really nice, the scenery and outdoor amenities were fantastic, and the host was super responsive to any questions we had and a delight to work with. Added bonuses were the nearby goats and Bilbo the cat who was super friendly :)"
Event Space for Families or Groups
Hillside Haven: Modern Retreat, Mountain Views
Private kitchen
Hillside Haven: Modern Retreat, Mountain Views
10.0 out of 10, Exceptional, (19)
"The property is beautiful and the house is spotless, tastefully decorated, and comfortable. We enjoyed a long weekend visiting wineries in the area. It is a bit of a drive to Charlottesville for dinner but it’s manageable. The management is very responsive to questions. We hope to stay here again."
The price is SAR 672
SAR 1,523 total
includes taxes & fees
24 Sep - 25 Sep
Hillside Haven: Modern Retreat, Mountain Views
One of the Best Views in Wintergreen!
Exterior
One of the Best Views in Wintergreen!
10.0 out of 10, Exceptional, (28)
"Title says it all, thank you!"
One of the Best Views in Wintergreen!
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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 property types in Wingina

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Entrance to High Ridge
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (253)
"This gorgeous townhouse was perfectly clean and very comfortable for our stay. The view is incredible! It is definitely a mountain getaway, so stock up on essentials before driving up there, but once you are there you won't be disappointed!!"
The price is SAR 372
SAR 834 total
includes taxes & fees
24 Sep - 25 Sep
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Fresh Private Hot Tub Lower Deck Relaxing Location in woods with Beautiful Views
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
9.6 out of 10, Exceptional, (275)
"Stayed here with some friends on a quick golf trip and it was an ideal spot. The house is well-maintained and having 4 full sized beds worked out great. The host is an excellent communicator and was quick to answer any questions we had. "
The price is SAR 615
SAR 1,509 total
includes taxes & fees
24 Sep - 25 Sep
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. Available August 26-31! BOOK NOW!
Good morning! Spectacular sunrise from the living room and deck!
Best views on Mountain! Breathtaking 5 Star. Available August 26-31! BOOK NOW!
10.0 out of 10, Exceptional, (219)
"Beautiful views and very accommodating hostess. Highly recommend."
Best views on Mountain! Breathtaking 5 Star. Available August 26-31! 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.