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

A deck with a fire pit, wooden chairs, and a view of the forest.

1. Mountain Mindset: Pup Friendly + Trail

Laurel Ridge

Caine C.

includes taxes & fees

20 Oct - 21 Oct

A rustic wooden cabin with a sign reading "Rusty's Retreat." It features large windows, a door, and is surrounded by a garden with plants and a large tree.

2. Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Afton

Caitlin S.

includes taxes & fees

21 Oct - 22 Oct

A wooden deck with wicker furniture, a brick wall, and a view of greenery.

3. Bluebird Cottage

Roseland

includes taxes & fees

20 Oct - 21 Oct

A wooden deck with a round table and chairs, a grill, and a trash can.

4. Afton Cottage w/ Hot Tub, Firepit, Mountain Views

Afton

Liz D.

includes taxes & fees

3 Nov - 4 Nov

A covered porch with two wooden chairs and a table, large windows, and a string of lights.

5. Modern Nellysford Getaway on 40 Private Acres!

Nellysford

includes taxes & fees

20 Oct - 21 Oct

6. Bluebird Cottage: Near 151 + Appalachian Trail

Roseland

Art B.

includes taxes & fees

20 Oct - 21 Oct

A wooden deck with a table and chairs, a railing, and a house with two windows.

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

Afton

includes taxes & fees

16 Nov - 17 Nov

A single-story house with a front porch, a pathway leading to the door, and a small garden with various plants and flowers.

8. The Cottage @ Afton Mountain- Close to Wineries!

Afton

Mary R.

includes taxes & fees

3 Nov - 4 Nov

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Top Wintergreen Hotel Reviews

Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

10/10 Excellent

"We were so fortunate to find this spectacular gem! The breathtaking views that pictures just cannot do justice for were amazing! The unit was so well stocked with all the essentials and one of the cleanest places we have stayed. Check-in and check-out were clear and simple. We can’t wait to book again. Thank you for sharing your piece of mountain with us. We loved it."

Family Retreat - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

10/10 Excellent

"The house was perfect. Kevin and Jen were VERY responsive to questions. I was unable to take the trash down to the dumpster and Kevin was super accommodating and offered a quick solution. We would absolutely stay there again. Highly recommended."

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace

10/10 Excellent

"Great unit. Clean and well supplied with everything you need if you plan to prepare meals. Communication with host (Rebecca) was excellent. If you are planning to eat out and don't want to drive a long distance down the mountain and outside the Wintergreen resort, options are limited. On the resort there are 2 pizza places (which we did not try), plus The Edge (we ate there twice and it was fine), plus Devil's Knob Grill (appears to be the nicest place) but it has a restrictive member/guest policy and staying in a VRBO does not qualify."

Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

10/10 Excellent

"What a lovely slopeside condo! Our family had a wonderful stay. The double bunk beds were perfect for our kids. And we loved watching the beautiful sunrise over the mountains. Everything was very clean and comfortable. Thank you for hosting us!"

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