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

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.
Valentine ❤️ getaway weekend! Charming cozy RIVERFRONT cottage on the Piney River
The Chestnut House. Welcome.

Valentine ❤️ getaway weekend! Charming cozy RIVERFRONT cottage on the Piney River

10.0 out of 10, Exceptional, (28)
"The property is beautiful, and the home is cozy and warm. There is plenty of living space, fully stocked with house needs and comfortable couches/beds. The fire pit is beautiful and the stream is so relaxing. Also plenty of yard for games and activities. Wonderful stay and just around the corner from break hikes, the i Erie’s and breweries. "
Valentine ❤️ getaway weekend! Charming cozy RIVERFRONT cottage on the Piney River
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)
"The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. "
The price is AED 731
AED 1,696 total
includes taxes & fees
3 Dec - 4 Dec
Pine Cottage: Hot Tub and Central to Nelson 151
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!"
Mountain Mindset: Hot Tub + 0.6 mile from Slopes
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!
Cottage w/ James River Access in Wingina!
Wingina Vacation Rental | 1BR | 1BA | 625 Sq Ft | 2 Steps to Enter

Cottage w/ James River Access in Wingina!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent clean friendly. Lived the dogs and decor. "
Cottage w/ James River Access in Wingina!
Bluebird Cottage: Near 151 + Appalachian Trail
Exterior

Bluebird Cottage: Near 151 + Appalachian Trail

2.0 star property
10.0 out of 10, Exceptional, (1)
"I wish we were staying longer than one night! This house is amazing! The decor is adorable mixing rustic with modern. The owners thought of everything someone might need. Shampoo, conditioner, soap, q-tips, flossers, coffee, non-dairy creamer, laundry soap and more! The location with the creek in the front is perfect. We sat on the screened in porch and just listened to the rushing water. I can't say enough wonderful things. We will most definitely be back and for longer. Thank you!"
The price is AED 437
AED 1,048 total
includes taxes & fees
2 Dec - 3 Dec
Bluebird Cottage: Near 151 + Appalachian Trail
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.
❤️️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 AED 613
AED 1,629 total
includes taxes & fees
1 Dec - 2 Dec
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
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, (11)
"This property is amazing. Location 10 Cleanliness 10 Communication 10 We were celebrating a milestone in a friends cancer remission journey (10 years) and felt so welcomed with a personalized gift and decorations. The details are always what matter! There was so much effort from the owners in making this experience special. This property was so nice, we really didn't want to leave with the accommodations and the back yard. When we did leave there was so much within walking distance or a...
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
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)
"My wife Teresa and I have been staying here for 11 years now. Every year for the last eleven years we have stayed the last week of Oct. The view is incredible. It never gets old. Something else that is very important to my wife and I is that the foyer door is only about 15 feet from the parking lot and its a flat walkway. Also, once in the foyer, its literally 2 steps to the stairs which are only 9 stairs. Most condos at Wintergreen are a hike just getting to the front door of the unit. Not...
The price is AED 514
AED 1,060 total
includes taxes & fees
30 Nov - 1 Dec
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
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, (65)
"The cabin is super cute and close to breweries. We had a great time and the host is amazing! "
The price is AED 477
AED 730 total
includes taxes & fees
28 Nov - 29 Nov
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Endless Mountain Top Views from All The Way Up!
Enjoy the stunning views from the balcony!

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (51)
"This was our second time at this location. It is well equipped, clean, comfortable and the location is great. It sits at the top of the ridge, so views of sunrise and the evening sky are beautiful. The owners are responsive and accommodating. We "
Endless Mountain Top Views from All The Way Up!
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

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