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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Wintergreen cottages

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.

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

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (21 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
The price is £130
includes taxes & fees
6 Oct - 7 Oct
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

2. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is £204
includes taxes & fees
5 Oct - 6 Oct
Bluebird Cottage
A covered porch with two wooden chairs and a table, large windows, and a string of lights.

3. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is £491
includes taxes & fees
6 Oct - 7 Oct
Modern Nellysford Getaway on 40 Private Acres!
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.
The price is £256
includes taxes & fees
14 Oct - 15 Oct
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

5. 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 £237
includes taxes & fees
5 Oct - 6 Oct
Bluebird Cottage: Near 151 + Appalachian Trail
A wooden deck with a table and chairs, a railing, and a house with two windows.

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

Artisan's Cottage: Woodsy+Private, Central to 151
Afton
The price is £237
includes taxes & fees
3 Nov - 4 Nov
Artisan's Cottage: Woodsy+Private, Central to 151
A stone wall, a small stream, and a house with a red roof.

7. 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, (32 reviews)
"Amazing haven in a quaint setting. Can’t wait to escape here again ! "
United States
Nicole B.
The price is £252
includes taxes & fees
25 Oct - 26 Oct
Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
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 £246
includes taxes & fees
4 Oct - 5 Oct
The Cottage @ Afton Mountain- Close to Wineries!
A two-story house with a wooden deck and a stone border.

9. 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 £363
includes taxes & fees
5 Oct - 6 Oct
Little Haven Cottage: Walk to Meade Tasting
A single-story house with a green exterior and a white porch.

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

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (115 reviews)
"This cute home was perfect for our stay in Crozet! It was close to lovely coffee shops. The home was very clean and communication with the host was fantastic! We would stay here again if in the area."
United States
Jody L.
The price is £252
includes taxes & fees
5 Oct - 6 Oct
High Street | Walk to Everything Crozet | Pet-Friendly
A two-story house with a porch, a front door, and a mailbox.

11. 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, (10 reviews)
"Looks brand new and very clean. Nice place."
United States
Ron C.
The price is £170
includes taxes & fees
3 Nov - 4 Nov
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
A house surrounded by trees with a clear sky.

12. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is £207
includes taxes & fees
3 Nov - 4 Nov
Artisan's Cottage
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

13. 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, (66 reviews)
"Lovely, charming home."
United States
Deborah R.
The price is £257
includes taxes & fees
2 Nov - 3 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.

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 £189
includes taxes & fees
26 Oct - 27 Oct
The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
A two-story white house with a front porch, a staircase, and a small front yard.

15. 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, (5 reviews)
The price is £316
includes taxes & fees
26 Oct - 27 Oct
Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
A house with a covered porch, a door, and a garden area with plants and a hose.

16. 40 Acre - Mechum Hill Guest Cottage

40 Acre - Mechum Hill Guest Cottage
Charlottesville
The price is £345
includes taxes & fees
11 Oct - 12 Oct
40 Acre - Mechum Hill Guest Cottage
A deck with wooden chairs and tables, overlooking a grassy field and distant mountains.

17. 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 £401
includes taxes & fees
30 Oct - 31 Oct
Cottage on Working Turkey and Bee Farm in the Heart of Crozet
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 £315
includes taxes & fees
4 Oct - 5 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
9.8 out of 10, Exceptional, (9 reviews)
"Loved this place for a short getaway. Great location!"
United States
Nicole M.
The price is £414
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 £410
includes taxes & fees
5 Oct - 6 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

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants

10/10 Excellent
"This well-equipped condo was central to the market and restaurants. We enjoyed the fireplace and the deck."
Lynne F. 4-night trip
Posted 4 days ago
Wintergreen Condo -Steps to Ski and restaurants

Find out more about Wintergreen

Wintergreen Cottages information

Number of reviews
367
Accommodation
32 Cottages
Lowest Price
£130
Highest Price
£491

Frequently asked questions

Why book your cottage in Wintergreen with Expedia?
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?
With Expedia's useful filter tool, comparing cheap cottages in Wintergreen is a snap. To discover stays that are friendly on the wallet, tailor your search results by amenities, star rating and budget.
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.