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Compare 92 Cottages in Wintergreen with updated reviews, rates, and availability.

Unique Cypress cottage, close to Charlottesville with mountain views.
Exterior

Unique Cypress cottage, close to Charlottesville with mountain views.

10.0 out of 10, Exceptional, (23)
"Really enjoyed our stay at this unique property, it is very pretty cottage in a nice area. Stayed here with my wife and parents to attend a wedding in Crozet. Very close to Monticello and some very cool walking trails. The host were very responsive and accommodating."
The price is AED 540
AED 1,041 total
includes taxes & fees
26 Nov - 27 Nov
Unique Cypress cottage, close to Charlottesville with mountain views.
Birds and Bees Cottage

Birds and Bees Cottage

10.0 out of 10, Exceptional, (39)
"Our hiking trip to Shenandoah Nat park was unexpectedly enhanced by our stay at Birds and Bees cottage! What a lovely, comfortable place with amazing view of the Blue Ridge Mountains and acres of pastures. The turkeys and llamas were so interesting to watch. I particularly liked when the turkeys gobbled in unison! The owners were very nice and informative. Would definitely stay again and recommend."
Birds and Bees Cottage
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
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!
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, (91)
"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 AED 735
AED 1,153 total
includes taxes & fees
1 Dec - 2 Dec
High Street | Walk to Everything Crozet | Pet-Friendly
Mechum Hill Cottage: Central to Crozet & Cville
Room

Mechum Hill Cottage: Central to Crozet & Cville

9.0 out of 10, Wonderful, (6)
"Great location, very nice accommodations. "
The price is AED 474
AED 973 total
includes taxes & fees
9 Dec - 10 Dec
Mechum Hill Cottage: Central to Crozet & Cville
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, (19)
"Our stay was nice and quiet, we had camp fires nightly, and while the train is loud it scarcely goes by. My only true issue was the long, uphill, potholed, gravel, dirt, and Mason block driveway was very difficult to ascend on motorcycles,. Overall it was a pleasure "
Isolated cottage with good view close to many winery and Brewers.
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors

Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors

10.0 out of 10, Exceptional, (41)
"Very peaceful and comfortable place to stay."
Charming Plainfields Cottage - Close to Charlottesville, Peaceful Outdoors
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.
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)
"My daughter and I absolutely loved our stay at Nonny Cottage. It was so peaceful to sit on the porch each morning and enjoy coffee while watching the deer! We took full advantage of the property's proximity to several trailheads. We love Crabtree Falls and even ventured to the Natural Bridge in Lexington. It was so nice to enjoy such a peaceful escape. The cottage was comfy, the kitchen had everything we needed, and loved being able to sleep with the windows open! Thank you fo a beautiful stay....
Cozy 'Nonny Cottage' Near Appalachian Trail!
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
The Firefly Cottage
Exterior

The Firefly Cottage

9.8 out of 10, Exceptional, (24)
"We felt like it was just the right amount privacy with a country vibe yet very close to Staunton. Everything was clean. The kitchen was equipped with everything we needed. We also appreciated that countertops were clear so there was plenty of room for our stuff. The bed was very comfortable. We would highly recommend this place for couples."
The Firefly Cottage
❤️️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. "
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
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
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
Cottage on the Farm
Exterior

Cottage on the Farm

10.0 out of 10, Exceptional, (2)
"It was so cute."
Cottage on the Farm
Pet-Friendly Devon Cottage at Ivy Cottages

Pet-Friendly Devon Cottage at Ivy Cottages

10.0 out of 10, Exceptional, (5)
"Overall a very nice clean and convenient location for visiting Charlottesville, VA. FYI the turn into the driveway, when headed east is a steep turn, which can be tricky at night the first time. One thing that would be nice is a compact washer & dryer unit; that said this is an excellent location in a beautiful setting."
Pet-Friendly Devon Cottage at Ivy Cottages
Pet-Friendly Somerset Cottage at Ivy Cottages

Pet-Friendly Somerset Cottage at Ivy Cottages

Pet-Friendly Somerset Cottage at Ivy Cottages
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
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
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, (283)
"We came to stay in this area to attend my best friend's wedding. There were around 100 guests at the wedding and everyone had rented a home in the area. Our location was perfect! We were near other guests, the venue, and several breweries. There were several activities planed at the resort as well. We were able to spend one day in Charlottesville as well but it was around a 50 minute drive. We really enjoyed the view and trails around the home. There are several balconies to relax on but we...
The price is AED 547
AED 1,407 total
includes taxes & fees
1 Dec - 2 Dec
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. Available Ski Season! BOOK NOW!
Good morning! Spectacular sunrise from the living room and deck!

Best views on Mountain! Breathtaking 5 Star. Available Ski Season! BOOK NOW!

10.0 out of 10, Exceptional, (226)
"Our annual girls weekends are our favorite time of year staying here. The coziness, the stunning views, and amazing host are unbeatable! "
Best views on Mountain! Breathtaking 5 Star. Available Ski Season! BOOK NOW!
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Living area

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

9.8 out of 10, Exceptional, (16)
"Our weekend was easily a 9;8 (a number we saw posted in the info you provided)...and we look forward to returning to this exact location...We loved the quality, uniqueness, and location of Traveler's Rest.....The weekend was as near perfect as it gets with the Condo, the food at The Echo, and the weather...The food and service at The Echo was excellent and deserves a higher rating than we saw...Denise and I had a really special experience, one that we won't forget...."
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
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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