Wintergreen Cottages

A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

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Our top choices for Wintergreen cottages

Mountain Mindset: Pup Friendly + Trail

Laurel Ridge

Caine C.

includes taxes & fees

20 July - 21 July

Bluebird Cottage

Roseland

includes taxes & fees

2 Aug - 3 Aug

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Afton

Joni K.

includes taxes & fees

2 Aug - 3 Aug

Modern Nellysford Getaway on 40 Private Acres!

Nellysford

includes taxes & fees

15 Aug - 16 Aug

Bluebird Cottage: Near 151 + Appalachian Trail

Roseland

Katherine N.

includes taxes & fees

20 July - 21 July

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton

Liz D.

includes taxes & fees

19 July - 20 July

The Cottage @ Afton Mountain- Close to Wineries!

Afton

Beth

includes taxes & fees

19 July - 20 July

Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls

Tyro

Michael W.

includes taxes & fees

26 July - 27 July

Artisan's Cottage: Woodsy+Private, Central to 151

Afton

Little Haven Cottage: Walk to Meade Tasting

Afton

"House was clean except for the two dirty hand towels lying on the bed when we arrived. Washer and dryer were behind a locked door so I had to message the host to get a code to open it. She first insisted it wouldn’t be inside a locked door, so I had to wait for her to find out about it and she replied quickly enough with the access code. I’m guessing nobody ever needed to use the washer before us? Strange. Rooms could have used dressers or something to put clothes in. Vanities in master...

Anonymous traveller

includes taxes & fees

30 July - 31 July

Unique Cypress cottage, close to Charlottesville with mountain views.

Charlottesville

Kurt K.

includes taxes & fees

9 Aug - 10 Aug

Cottage, Private Bathroom (Basecamp Cottage) | Exterior

Little Haven Cottage

Afton

includes taxes & fees

19 July - 20 July

High Street | Walk to Everything Crozet | Pet-Friendly

Crozet

Anonymous traveller

includes taxes & fees

28 July - 29 July

Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries

Charlottesville

includes taxes & fees

10 Aug - 11 Aug

Petite Pink Cottage, Perfect for Solo Travelers

Charlottesville

Peter S.

includes taxes & fees

19 July - 20 July

Dog Friendly Cottage Close to UVA

Charlottesville

Eric W.

includes taxes & fees

18 July - 19 July

Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom

Charlottesville

Carol F.

includes taxes & fees

17 Aug - 18 Aug

The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!

Staunton

Pam W.

includes taxes & fees

16 Aug - 17 Aug

Artisan's Cottage

Afton

includes taxes & fees

20 July - 21 July

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Top Wintergreen Hotel Reviews

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

10/10 Excellent

"Beautiful view! The condo was very cleanAnd check in was easy."

Wintergreen Luxury, Best Views in VA!

10/10 Excellent

"Was everything we expected...and then some! Stayed for 2 weeks. Had 9 adults and 4 children. Additional 4 adults joined for a day visit. We utilized all the bedrooms and bathrooms...and all were very comfortable, well appointed, well supplied and in full working order (tubs, showers, sinks, etc.). We used all the home had to offer, like the hot tub, sauna, both outdoor fire pits, inside fireplace, outdoor grills, all three decks, main floor and mid floor TVs, arcade games, and pool table...and all were in great working order. The kitchen was well appointed with a fully stocked coffee mess...and had everything we needed. Several of our group needed to remote work a few of the days and they had no issues as the WiFi was strong and solid. Plenty of room for all!The Wintergreen Market, Lodge, shopes and restaurants were walkable from the house. We enjoyed all the events Wintergreen offered for our 4th of July celebration to include food, crafts, activities, live music and fireworks. We visited Lake Sherando for swimming...and also made a few trips into Waynesboro for groceries. We hiked several of the local trails near the home...some were very challenging. Favorite for the kids was Upper Shamokln Falls. Enjoyed several of the many wineries and breweries around Nellysford. Also enjoyed Beltsies for breakfast a few times.Favorite of all were the amazing mountain views this home offers...words or pics cannot capture them! Host was very responsive whenever we reached out."

Mountain Cabin · Hot Tub · Pool Table · Ridge Views · Grill · Arcade · Hiking

10/10 Excellent

"If you are looking for the perfect place to gather as a family (or friends)! Everyone can be together at times - and have their private space at times - this is it! The house is beautiful and the views are exquisite. It is very well appointed with even more than similar properties in the area that we've visited (for example, a thermometer for cooking). The pool table and equipment were well-kept, and included two junior pool sticks for smaller children (a wonderful touch). Wifi is superb - which is a must in this area - if you wish to receive emails or make calls. The extra blankets were nice. The hot-tub worked very well and had a gorgeous view. We loved all three levels. Each provided exactly the right amount of perfect. One room to play; one room to gather and cook and be together; the other a nice respite from a long day. What is also very important -- everything worked! The grill had a full gas tank, the disposal did its job, the ice machine (another nice touch) worked to perfection. You can tell the hosts really care about making this a comfortable and welcoming environment for their guests. Check-in was a breeze and communication with the hosts was outstanding. We could not recommend this place more. We fell in love with the pictures - and our experience here exceeded our expectations! It is also a 5 minute drive to the blue ridge overlook (a must for pics) and right near a trailhead. We have stayed at Wintergreen almost a dozen times, this place was the best!"

Best views on Mountain! Breathtaking 5 Star condo! Book Summer and Fall now!

10/10 Excellent

"Wonderful condo, exactly as described with everything you could need for a mountain getaway. We stay at Wintergreen a few times a year and this was far and away our favorite place to stay. The host was also wondering and responsive when I had a few questions. Can't wait to stay again in the future."

Cozy Cabin with private HOT TUB!

8/10 Good

"The property was fine. The only thing that I could say to improve the description of the property is to forewarn the people coming about the steepness of the drive to the cabin. I have rented cabins elsewhere, and that one was the steepest drive that I have ever had to get to a cabin."

Find out more about Wintergreen