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Compare 89 Cottages in Wintergreen with updated reviews, rates, and availability.

Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
The Chestnut House. Welcome.

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

10.0 out of 10, Exceptional, (32)
"We booked this property for a weekend break, and it was everything we hoped for and more! Pictures are accurate but can't possibly capture the impeccably designed and decorated house or the idyllic surroundings.The house was perfect for four adults, with a kitchen that rivals any we have seen. Everything, from the bed linens and bath towels to the kitchen supplies and wood fireplace, made our stay easy and special.We stayed on a rainy weekend, but the nearby Craft Beverage Trail (Nelson 151) was...
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

9.8 out of 10, Exceptional, (22)
"Three couples enjoyed this well appointed home….plenty of room and beautiful views. It was convenient to some great restaurants and wineries. We definitely will visit this area again!"
The price is SAR 510
SAR 1,537 total
includes taxes & fees
24 Feb - 25 Feb
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
Bluebird Cottage: Near 151 + Appalachian Trail
Exterior

Bluebird Cottage: Near 151 + Appalachian Trail

2.0 star property
7.6 out of 10, Good, (5)
"Close to Wintergreen ski resort in quiet spot out of chaos.Simplistic & cozy cabin. Sleeps 4 adults but lots of space for blow ups & have 3 more guests. Bring extra blankets if you sleep with more than one. Clean. No issues. Nice getaway to hike, read, paint, bird, ski or just reset. Loved it! "
The price is SAR 446
SAR 1,112 total
includes taxes & fees
24 Feb - 25 Feb
Bluebird Cottage: Near 151 + Appalachian Trail
The Firefly Cottage
Exterior

The Firefly Cottage

9.8 out of 10, Exceptional, (26)
"Had a wonderful getaway! So enjoyed our time together, exploring Staunton, and spending quiet time on the property watching the farm animals. "
The Firefly Cottage
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, (128)
"We had a family get together and everything was fantastic."
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Property grounds

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

9.6 out of 10, Exceptional, (5)
"House was perfect for a quick getaway. Clean, had everything you’d need to unwind and get away. "
The price is SAR 547
SAR 1,233 total
includes taxes & fees
24 Feb - 25 Feb
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
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!
Cozy 'Nonny Cottage' Near Appalachian Trail!
Vesuvius Vacation Rental | 2BR | 1BA | 896 Sq Ft | Exterior Steps Required

Cozy 'Nonny Cottage' Near Appalachian Trail!

9.6 out of 10, Exceptional, (16)
"The nonny cottage had everything my husband and I needed for our off the grid fall trip to celebrate his birthday and our wedding anniversary. The cottage was close the the hiking trails we wanted to explore and not too far out we couldn't travel into town for a nice dinner celebration for his birthday, the Southern Inn in Lexington was superb. Thanks for the fabulous stay!"
Cozy 'Nonny Cottage' Near Appalachian Trail!
Cute Getaway in the Heart of Nelson County Hosted by Heather
Open dining room and kitchen

Cute Getaway in the Heart of Nelson County Hosted by Heather

10.0 out of 10, Exceptional, (3)
"Great place"
Cute Getaway in the Heart of Nelson County Hosted by Heather
Serene Roseland Retreat Near Wintergreen Resort!
Terrace/patio

Serene Roseland Retreat Near Wintergreen Resort!

3.0 star property
Serene Roseland Retreat Near Wintergreen Resort!
Pet-Friendly Somerset Cottage at Ivy Cottages

Pet-Friendly Somerset Cottage at Ivy Cottages

Pet-Friendly Somerset Cottage at Ivy Cottages
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, (12)
"Rented out this little cottage for my daughter's 15th birthday celebration and it was the best rental we have ever stayed at. The details in the home were perfectly set, from the medicine cabinet to the fully stocked kitchen. There was absolutely nothing I could have brought with us that wasn't available already. Waking up to the sound of the creek, looking at the mountainside from the porch was next to perfection. This cottage exceeded all of my expectations when looking for a retreat from...
Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.
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 SAR 746
SAR 1,782 total
includes taxes & fees
4 Mar - 5 Mar
Pine Cottage: Hot Tub and Central to Nelson 151
High Street | Walk to Everything Crozet | Pet-Friendly
High Street Cottage

High Street | Walk to Everything Crozet | Pet-Friendly

9.8 out of 10, Exceptional, (93)
"Great location for getting to restaurants and the park with kids. House was exactly as described and perfect for a quick getaway. Close to Charlottesville too. "
The price is SAR 750
SAR 1,197 total
includes taxes & fees
24 Feb - 25 Feb
High Street | Walk to Everything Crozet | Pet-Friendly
"The Sparrow" at Historic Downtown Staunton
Welcome to The Sparrow!

"The Sparrow" at Historic Downtown Staunton

10.0 out of 10, Exceptional, (12)
"Adorable house, lovely host, wonderful location."
"The Sparrow" at Historic Downtown Staunton
Isolated cottage with good view close to many winery and Brewers.
Exterior

Isolated cottage with good view close to many winery and Brewers.

9.0 out of 10, Wonderful, (21)
"This was perfect for our weekend trip to the 151 breweries/wineries. Very cute house and very clean. We would come back!"
Isolated cottage with good view close to many winery and Brewers.
Cottage on the Farm
Exterior

Cottage on the Farm

10.0 out of 10, Exceptional, (2)
"It was so cute."
Cottage on the Farm
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
Rosé All Day: Wine Country Getaway! Walk to Dining
Welcome to Rosé All Day, a cottage in the heart of Virginia's wine country.

Rosé All Day: Wine Country Getaway! Walk to Dining

2.0 star property
10.0 out of 10, Exceptional, (10)
"We were in town for work and needed a comfortable place to come back to at the end of our long days. The beds were extremely comfortable, and the hosts were so responsive! Such a charming house with a great location! We would love to stay again!"
Rosé All Day: Wine Country Getaway! Walk to Dining
Beautiful Cottage at Historic Ramsay Estate with "WOW" Blue Ridge views

Beautiful Cottage at Historic Ramsay Estate with "WOW" Blue Ridge views

10.0 out of 10, Exceptional, (42)
"Loved walking the estate and the real fireplace"
Beautiful Cottage at Historic Ramsay Estate with "WOW" Blue Ridge views
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 Wintergreen

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, (294)
"Cozy, Clean and Convenient!"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Our upper-floor condo is just steps to the car & firewood, provided nearby

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

10.0 out of 10, Exceptional, (309)
"Clean, cozy,and convenient!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Wintergreen Condo -Steps to Ski and restaurants
Living Room with fireplace

Wintergreen Condo -Steps to Ski and restaurants

9.8 out of 10, Exceptional, (9)
"Best price and a perfect little condo just a short walk to the ski lifts. An old man, 3 teenagers, and my mini me, truly enjoyed it. It has all you need to cook and chill out after a long day on the slopes. The fireplace with a constant supply of wood was the sugar on top. Thanks for a great stay."
The price is SAR 356
SAR 905 total
includes taxes & fees
25 Feb - 26 Feb
Wintergreen Condo -Steps to Ski and restaurants
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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