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

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Wintergreen cottages

Exterior

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

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (18 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
The price is £122
includes taxes & fees
24 Aug - 25 Aug
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Cottage, Private Bathroom (Bluebird Cottage) | Exterior

2. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is £199
includes taxes & fees
25 Aug - 26 Aug
Bluebird Cottage
Exterior

3. Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail
Roseland
8.8 out of 10, Excellent, (12 reviews)
"Cute cottage close to the slopes, Recommend 4WD if visiting in the winter snow."
United States
Art B.
The price is £228
includes taxes & fees
24 Aug - 25 Aug
Bluebird Cottage: Near 151 + Appalachian Trail
House (3 Bedrooms) | Interior

4. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is £480
includes taxes & fees
27 Aug - 28 Aug
Modern Nellysford Getaway on 40 Private Acres!
Outdoor dining

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

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
9.6 out of 10, Exceptional, (15 reviews)
"Our stay was fantastic! Great location for wineries and hiking. Perfect for a couples getaway for privacy and quaintness. Will definitely consider booking again if we ever come back to the area!! "
United States
Liz D.
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Property grounds

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

Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
Tyro
10.0 out of 10, Exceptional, (31 reviews)
"Amazing haven in a quaint setting. Can’t wait to escape here again ! "
United States
Nicole B.
The price is £254
includes taxes & fees
20 Aug - 21 Aug
Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
Exterior

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

Artisan's Cottage: Woodsy+Private, Central to 151
Afton
The price is £232
includes taxes & fees
20 Aug - 21 Aug
Artisan's Cottage: Woodsy+Private, Central to 151
Exterior

8. Little Haven Cottage: Walk to Meade Tasting

Little Haven Cottage: Walk to Meade Tasting
Afton
6.0 out of 10, (1 review)
"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...
United States
Anonymous traveller
The price is £320
includes taxes & fees
16 Sept - 17 Sept
Little Haven Cottage: Walk to Meade Tasting
Exterior

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

Unique Cypress cottage, close to Charlottesville with mountain views.
Charlottesville
10.0 out of 10, Exceptional, (64 reviews)
"Great stay, very friendly, responsive owners."
United States
David F.
The price is £210
includes taxes & fees
24 Aug - 25 Aug
Unique Cypress cottage, close to Charlottesville with mountain views.
Exterior

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

Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
Charlottesville
9.2 out of 10, Wonderful, (7 reviews)
"Such a cozy, secluded cottage! Great place to hang with my besties. We really enjoyed our time at Wandering Bear. "
United States
Carol F.
The price is £157
includes taxes & fees
7 Sept - 8 Sept
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
Exterior

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

Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
Charlottesville
10.0 out of 10, Exceptional, (2 reviews)
"We spent a wonderful weekend with our family at this home. We arrived early and Austen was very accommodating and we were able to check in much earlier (he was also super nice when we were late checking out whoops!). The house is very cozy and family friendly. Beds were soft. The kitchen had everything you would need although no oven (not a big deal). We were glad for the washer/dryer combo until and our kids were very happy for the playground right by the house. Couldn’t be happier with our...
United States
James D.
The price is £261
includes taxes & fees
24 Aug - 25 Aug
Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
Cottage, Private Bathroom (Artisan's Cottage) | Exterior

12. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is £202
includes taxes & fees
25 Aug - 26 Aug
Artisan's Cottage
Exterior

13. High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (113 reviews)
"Great little spot, very close to “downtown” Crozet. Great host, great communication…."
United States
Anonymous traveller
The price is £245
includes taxes & fees
31 Aug - 1 Sept
High Street | Walk to Everything Crozet | Pet-Friendly
Exterior

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

The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
Staunton
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful visit. Beautifully landscaped and, clean property. Peaceful- hope to visit again."
United States
Pam W.
The price is £185
includes taxes & fees
23 Aug - 24 Aug
The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
Exterior

15. Dog Friendly Cottage Close to UVA

Dog Friendly Cottage Close to UVA
Charlottesville
10.0 out of 10, Exceptional, (5 reviews)
"Property was very clean and exactly what we needed. Location is perfect to explore wineries and breweries in both directions. Entrance does sneak up on you at night but no biggie! "
United States
Eric W.
The price is £369
includes taxes & fees
28 Aug - 29 Aug
Dog Friendly Cottage Close to UVA
Exterior

16. Charming Cottage Near Vineyards

Charming Cottage Near Vineyards
Charlottesville
10.0 out of 10, Exceptional, (7 reviews)
"Loved this place for a short getaway. Great location!"
United States
Nicole M.
The price is £375
includes taxes & fees
23 Aug - 24 Aug
Charming Cottage Near Vineyards
Exterior

17. Classic Virginia Cottage, 10 min to UVA and Vineyards

Classic Virginia Cottage, 10 min to UVA and Vineyards
Charlottesville
The price is £375
includes taxes & fees
20 Aug - 21 Aug
Classic Virginia Cottage, 10 min to UVA and Vineyards
Cottage, Private Bathroom (Basecamp Cottage) | Exterior

18. Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
The price is £288
includes taxes & fees
1 Sept - 2 Sept
Little Haven 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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Top Wintergreen Hotel Reviews

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

10/10 Excellent
"Our family loved the house."
Leslie H. 3-night trip
Posted 1 day ago
Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Find out more about Wintergreen

Wintergreen Cottages information

Number of reviews
277
Accommodation
34 Cottages
Lowest Price
£122
Highest Price
£480

Frequently asked questions

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What is there to do in Wintergreen near my cottage?
Once you've checked in to your hotel, venture out and discover the fantastic things Wintergreen has to offer. Wintergreen Resort is a top attraction to add to your travel itinerary.