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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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

Mountain Mindset: Pup Friendly + Trail
Laurel Ridge
9.6 out of 10, Exceptional, (10 reviews)
"Nice cabin in a good location! "
United States
Caine C.
The price is €784
includes taxes & fees
20 Oct - 21 Oct
Mountain Mindset: Pup Friendly + Trail
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

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (22 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
The price is €154
includes taxes & fees
21 Oct - 22 Oct
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

3. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is €261
includes taxes & fees
20 Oct - 21 Oct
Bluebird Cottage
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 Cottage w/ Hot Tub, Firepit, Mountain Views
Afton
9.6 out of 10, Exceptional, (17 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
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!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is €578
includes taxes & fees
20 Oct - 21 Oct
Modern Nellysford Getaway on 40 Private Acres!
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

6. Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail
Roseland
9.0 out of 10, Wonderful, (14 reviews)
"Cute cottage close to the slopes, Recommend 4WD if visiting in the winter snow."
United States
Art B.
The price is €301
includes taxes & fees
20 Oct - 21 Oct
Bluebird Cottage: Near 151 + Appalachian Trail
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

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

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (37 reviews)
"A lovely place to stay and relax! Not far to get to wineries and to Charlottesville. Thank you for a lovely stay!"
United States
Mary R.
The price is €300
includes taxes & fees
3 Nov - 4 Nov
The Cottage @ Afton Mountain- Close to Wineries!
A stone wall, a small stream, and a house with a red roof.

9. 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, (33 reviews)
"Amazing haven in a quaint setting. Can’t wait to escape here again ! "
United States
Nicole B.
The price is €300
includes taxes & fees
25 Oct - 26 Oct
Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
A two-story house with a wooden deck and a stone border.

10. 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 €460
includes taxes & fees
20 Oct - 21 Oct
Little Haven Cottage: Walk to Meade Tasting
A single-story house with a green exterior and a white porch.

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

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (116 reviews)
"perfect location to montfair resort where we attended wedding...coffee within walking distance, very clean house, kitchen well stocked, had a fantastic time ..highly recommend you visit here for your stay..."
United States
karen r.
The price is €303
includes taxes & fees
21 Oct - 22 Oct
High Street | Walk to Everything Crozet | Pet-Friendly
A two-story house with a porch, a front door, and a mailbox.

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

Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
Charlottesville
9.4 out of 10, Exceptional, (13 reviews)
"Looks brand new and very clean. Nice place."
United States
Ron C.
The price is €200
includes taxes & fees
27 Oct - 28 Oct
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
A house surrounded by trees with a clear sky.

13. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is €266
includes taxes & fees
16 Nov - 17 Nov
Artisan's Cottage
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

14. 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, (67 reviews)
"Great stay, very friendly, responsive owners."
United States
David F.
The price is €256
includes taxes & fees
18 Nov - 19 Nov
Unique Cypress cottage, close to Charlottesville with mountain views.
A two-story house with a large lawn, surrounded by mature trees and a white picket fence.

15. 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 €233
includes taxes & fees
20 Oct - 21 Oct
The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
A deck with wooden chairs and tables, overlooking a grassy field and distant mountains.

16. Cottage on Working Turkey and Bee Farm in the Heart of Crozet

Cottage on Working Turkey and Bee Farm in the Heart of Crozet
Crozet
10.0 out of 10, Exceptional, (45 reviews)
"Lovely little space on a great working farm. Cozy, quiet, and proximity to plenty of amazing nature and activities. Highly recommended "
United States
Thomas G.
The price is €390
includes taxes & fees
30 Oct - 31 Oct
Cottage on Working Turkey and Bee Farm in the Heart of Crozet
A two-story white house with a front porch, a staircase, and a small front yard.

17. 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, (9 reviews)
The price is €351
includes taxes & fees
16 Nov - 17 Nov
Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

18. Petite Pink Cottage, Perfect for Solo Travelers

Petite Pink Cottage, Perfect for Solo Travelers
Charlottesville
10.0 out of 10, Exceptional, (9 reviews)
"Such a cute little cabin!!!! Loved it! "
United States
Beth V.
The price is €408
includes taxes & fees
29 Oct - 30 Oct
Petite Pink Cottage, Perfect for Solo Travelers
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

19. Charming Cottage Near Vineyards

Charming Cottage Near Vineyards
Charlottesville
10.0 out of 10, Exceptional, (11 reviews)
"Loved this place for a short getaway. Great location!"
United States
Nicole M.
The price is €457
includes taxes & fees
3 Nov - 4 Nov
Charming Cottage Near Vineyards
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

20. Cornwall Cottage at Ivy Cottages | Country Living Near Charlottesville

Cornwall Cottage at Ivy Cottages | Country Living Near Charlottesville
Charlottesville
8.0 out of 10, Very good, (2 reviews)
"Very clean and roomy for 2 people."
United States
Glenn C.
The price is €481
includes taxes & fees
26 Oct - 27 Oct
Cornwall Cottage at Ivy Cottages | Country Living Near Charlottesville
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

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

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."
Traci A. 3-night trip
Posted 22 hours ago
Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

Find out more about Wintergreen

Wintergreen Cottages information

Number of reviews
399
Accommodation
33 Cottages
Lowest Price
€154
Highest Price
€784

Frequently asked questions

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We think that vacays should be easy, so if you're seeking cottages in Wintergreen at a nice price, Expedia has you covered. Keep the budget under control and choose a wallet-friendly option surrounded by wilderness, or splurge on a luxury cottage to treat your loved ones.
How can I find cheap cottages in Wintergreen?
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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.