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Compare 65 Cottages in Wingina with updated reviews, rates, and availability.

Charming cottage on Piney River. Host your Thanksgiving in our chefs kitchen.
The Chestnut House. Welcome.
Charming cottage on Piney River. Host your Thanksgiving in our chefs kitchen.
10.0 out of 10, Exceptional, (24)
"This property is first class with top of the line kitchen. Right on the beautiful Piney River...so peaceful. Hope to visit again for a longer stay!"
Charming cottage on Piney River. Host your Thanksgiving in our chefs kitchen.
Charming Cottage < 10 Mi to Wineries & Skiing!
Nellysford Vacation Rental | 2BR | 1BA | 980 Sq Ft | Stairs Required for Entry
Charming Cottage < 10 Mi to Wineries & Skiing!
10.0 out of 10, Exceptional, (11)
"The cottage is so charming and has the best location! It’s very close to many wineries and breweries. Check in and check out we’re seamless. We had a great stay. "
Charming Cottage < 10 Mi to Wineries & Skiing!
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
Welcome view of the Piney River cottage
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
9.8 out of 10, Exceptional, (123)
"This lovely little cottage on the piney river was the perfect place to celebrate 35 years of marriage. The setting was beautiful and the accommodations spacious yet intimate. The cottage demonstrates an obvious history of love and good memories. We fished the section of river assigned and got skunked. The beauty of the setting was more than compensation for this disappointment. The owners have set up a welcoming, warm and friendly vibe that made it a pleasure to stay at Sycamore Shade. We...
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
Pine Cottage: Hot Tub and Central to Nelson 151
Exterior
Pine Cottage: Hot Tub and Central to Nelson 151
10.0 out of 10, Exceptional, (16)
"Need to step back and regroup and refresh and the cottage was perfect. Quiet, hot tub under the stars and a good night sleep was what the dr ordered !! Thank you!!"
The price is SAR 748
SAR 1,727 total
includes taxes & fees
3 Dec - 4 Dec
Pine Cottage: Hot Tub and Central to Nelson 151
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
10.0 out of 10, Exceptional, (19)
"This house was absolutely perfect for a quiet weekend getaway. "
The price is SAR 605
SAR 1,638 total
includes taxes & fees
12 Nov - 13 Nov
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
James River Cottage with 2 Kayaks
Miscellaneous
James River Cottage with 2 Kayaks
8.0 out of 10, Very Good, (3)
"Absolutely wonderful stay. Just right for 2 ….. walked along the river (didn’t have time for the kayaks I’m afraid…). Sat out side under the patio in the back…. super quiet. Ran the quiet country road in the morning. Very comprehensive kitchen set up….hot showers and the best towels ever. Not bougie….very homey. Really enjoyed it. Highly recommend."
James River Cottage with 2 Kayaks
Mountain Mindset: Hot Tub + 0.6 mile from Slopes
Outdoor dining
Mountain Mindset: Hot Tub + 0.6 mile from Slopes
9.6 out of 10, Exceptional, (4)
"We enjoyed the impeccable details in the renovated space. Very comfortable and upscale. Highly recommend to others!"
The price is SAR 1,202
SAR 3,025 total
includes taxes & fees
12 Nov - 13 Nov
Mountain Mindset: Hot Tub + 0.6 mile from Slopes
Quiet Blue Ridge Mountain Cottage
Living Room 2
Quiet Blue Ridge Mountain Cottage
9.6 out of 10, Exceptional, (82)
"This is a delightful, quiet & clean little cabin. We enjoyed exploring the area then cooking dinner at home and spending time together. Thank you!"
Quiet Blue Ridge Mountain Cottage
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
Property grounds
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
10.0 out of 10, Exceptional, (7)
"We had a wonderful stay here. The host was great to us in making our stay go smooth with out any problems. The area was beautiful and the nice large fenced in yard was great for our dogs to explore. The whole property was VERY well maintained inside and out, comfortable accommodations and supplied with everything we needed to feel home away from home. We wouldn't hesitate to book again anytime of year!"
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
Beautiful, Remodeled Cottage in the Heart of Afton
Cottage Entrance
Beautiful, Remodeled Cottage in the Heart of Afton
10.0 out of 10, Exceptional, (61)
"We had a great time at the cottage. It is located conveniently to Skyline Drive. We were able to pick some chestnuts at a Virginia Chestnut farm. Paulie's Pig Out just down the road had tasty BBQ. "
Beautiful, Remodeled Cottage in the Heart of Afton
Blue Ridge Cottage
Terrace/patio
Blue Ridge Cottage
10.0 out of 10, Exceptional, (2)
"This listing met our needs perfectly, house was clean and cozy, host was communicative and had awesome personalized touches for our party. Really great."
Blue Ridge Cottage
Charming Lakefront Cabin: Fish, Hike & More!
Exterior
Charming Lakefront Cabin: Fish, Hike & More!
2.0 star property
Charming Lakefront Cabin: Fish, Hike & More!
Luxury Retreat Perfect for Reconnecting w/ Nature
Luxury Retreat Perfect for Reconnecting w/ Nature
10.0 out of 10, Exceptional, (4)
"This place was top notch! We had been awaiting this stay and it more than exceeding our expectations for our 10th anniversary. The website was a great touch and communication before and during our stay was excellent. Beautiful place with all the little touches one could ask for. Perfect location for a quiet getaway and to jump to Charlottesville and the numerous area wineries. We definitely want to come back as it was everything we could ask for."
Luxury Retreat Perfect for Reconnecting w/ Nature
Charming Cottage < 10 Mi to Wineries & Skiing!
Exterior
Charming Cottage < 10 Mi to Wineries & Skiing!
3.0 star property
Charming Cottage < 10 Mi to Wineries & Skiing!
Wintergreen Resort Home w/ 2 Decks + Ski Access!
Dining
Wintergreen Resort Home w/ 2 Decks + Ski Access!
3.0 star property
Wintergreen Resort Home w/ 2 Decks + Ski Access!
Hot Tub! Short walk to Three Notch'd - Charming Mid-Century Modern Cottage!
Enjoy the Back yard complete with Hot tub nestled under twinkle lights overlooking the fire pit stocked with wood. Corn hole and bear pong available to play in the grass.
Hot Tub! Short walk to Three Notch'd - Charming Mid-Century Modern Cottage!
10.0 out of 10, Exceptional, (9)
"The home was beautiful and very clean. The best part of the home was the fact that it was in such a great location for the local brewers, distilleries etc. However the property exceeded our wants and needs. The owner stoked the home nicely and we never had to worry about little things like paper products, soaps etc. we enjoyed our girls weekend! We would definitely rent again! "
The price is SAR 648
SAR 2,040 total
includes taxes & fees
20 Nov - 21 Nov
Hot Tub! Short walk to Three Notch'd - Charming Mid-Century Modern Cottage!
Wintergreen Home w/ Deck - Near Skiing & Hiking!
Living area
Wintergreen Home w/ Deck - Near Skiing & Hiking!
3.0 star property
Wintergreen Home w/ Deck - Near Skiing & Hiking!
JULY DISCOUNT! Romantic 2 BR 2 story w/mountain views and stunning outdoor space
Property grounds
JULY DISCOUNT! Romantic 2 BR 2 story w/mountain views and stunning outdoor space
JULY DISCOUNT! Romantic 2 BR 2 story w/mountain views and stunning outdoor space
Cozy Cottage with beautiful Mountain View’s - close to wineries
Miscellaneous
Cozy Cottage with beautiful Mountain View’s - close to wineries
10.0 out of 10, Exceptional, (10)
"This is my second stay in this beautiful home. The location at Wintergreen is wonderful, it is away from all the commotion at the top of the mountain. Beautiful scenery and gorgeous sunsets. The home has everything you will need for a wonderful stay. Fabulous hosts that can be contacted at any time. Should you need to, But you likely won’t need to because everything is available in the house."
Cozy Cottage with beautiful Mountain View’s - close to wineries
Nellysford Home ~ 10 Mi to Wintergreen Resort
Dining
Nellysford Home ~ 10 Mi to Wintergreen Resort
3.0 star property
9.0 out of 10, Wonderful, (2)
"Fantasically appointed home that was an easy drive to Wintergreen. My family would stay here again."
Nellysford Home ~ 10 Mi to Wintergreen Resort
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, (256)
"This is a great place with an incredible view. The unit is nicely appointed with quality dishware, glasses, towels etc. We had a small problem with the TV when we checked in and the owner drove 2-3 hours to deliver a new TV the next morning. You just cannot beat that kind of service. We had a few guests during our month-long stay and every one was very taken with the place. Highly recommend."
The price is SAR 526
SAR 1,038 total
includes taxes & fees
30 Nov - 1 Dec
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, (281)
"Great place to relax. Much better than a Condo."
The price is SAR 560
SAR 1,443 total
includes taxes & fees
11 Nov - 12 Nov
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Cabin sits on host's 34-acre mountain property. Private guest driveway/parking.
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
10.0 out of 10, Exceptional, (63)
"Beautiful ca)bin in mountainess area of Va. Cabin is updated and)nicenicenicethe"
The price is SAR 488
SAR 751 total
includes taxes & fees
12 Nov - 13 Nov
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
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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