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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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, (19 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
The price is CA $92
CA $236 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $160
CA $374 total
includes taxes & fees
Sep 14 - Sep 15
Bluebird Cottage
A small house with a porch and a large tree in front.

3. 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 CA $160
CA $424 total
includes taxes & fees
Sep 14 - Sep 15
Bluebird Cottage: Near 151 + Appalachian Trail
A covered porch with two wooden chairs and a table, large windows, and a string of lights.

4. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is CA $379
CA $902 total
includes taxes & fees
Sep 14 - Sep 15
Modern Nellysford Getaway on 40 Private Acres!
A wooden deck with a round table and chairs, a grill, and a trash can.

5. 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 CA $217
CA $465 total
includes taxes & fees
Sep 21 - Sep 22
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
A single-story house with a front porch, a chimney, and a gravel driveway.

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

Artisan's Cottage: Woodsy+Private, Central to 151
Afton
The price is CA $184
CA $455 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $279
CA $479 total
includes taxes & fees
Sep 23 - Sep 24
Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
A two-story house with a deck, a green door, and a sign reading 'Ladle House Cottage.'

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 CA $234
CA $654 total
includes taxes & fees
Sep 14 - Sep 15
Little Haven Cottage: Walk to Meade Tasting
A single-story house with a green exterior and a white porch.

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

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (114 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 CA $277
CA $467 total
includes taxes & fees
Sep 14 - Sep 15
High Street | Walk to Everything Crozet | Pet-Friendly
A two-story white house with a front porch, a staircase, and a small front yard.

10. 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, (4 reviews)
"This is a phenomenal property and space. The beds were so comfortable. The space is private, and well appointed with everything you need! Enjoyed the fire ring and the back porch immensely. As a work traveler, you don’t get many chances to sit and relax in such a refined and great space, this is a gem. Oh and Harris Teeter is just down the road for all the groceries and supplies!"
United States
Dan H.
The price is CA $277
CA $596 total
includes taxes & fees
Sep 28 - Sep 29
Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
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, (7 reviews)
"Looks brand new and very clean. Nice place."
United States
Ron C.
The price is CA $243
CA $316 total
includes taxes & fees
Sep 22 - Sep 23
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 CA $173
CA $389 total
includes taxes & fees
Sep 28 - Sep 29
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, (65 reviews)
"Lovely, charming home."
United States
Deborah R.
The price is CA $270
CA $480 total
includes taxes & fees
Oct 5 - Oct 6
Unique Cypress cottage, close to Charlottesville with mountain views.
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

14. 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 CA $513
CA $700 total
includes taxes & fees
Sep 14 - Sep 15
Dog Friendly Cottage Close to UVA
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 CA $235
CA $380 total
includes taxes & fees
Oct 6 - Oct 7
The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

16. 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 CA $420
CA $569 total
includes taxes & fees
Sep 14 - Sep 15
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.

17. 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 CA $513
CA $700 total
includes taxes & fees
Oct 4 - Oct 5
Charming Cottage Near Vineyards
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

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

Classic Virginia Cottage, 10 min to UVA and Vineyards
Charlottesville
The price is CA $513
CA $700 total
includes taxes & fees
Sep 23 - Sep 24
Classic Virginia Cottage, 10 min to UVA and Vineyards
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

19. 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 CA $562
CA $768 total
includes taxes & fees
Oct 5 - Oct 6
Cornwall Cottage at Ivy Cottages | Country Living Near Charlottesville
A two-story house with a wooden deck and a stone border.

20. Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
The price is CA $234
CA $575 total
includes taxes & fees
Sep 14 - Sep 15
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

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

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

10/10 Excellent
"Great condo within walking distance to all the restaurants and lifts. Highly recommend!"
Debra L. 2-night trip
Posted 6 days ago
Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

Find out more about Wintergreen

Wintergreen Cottages information

Number of reviews
282
Accommodation
34 Cottages
Lowest Price
CA $236
Highest Price
CA $902

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.

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