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 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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 CA $374
CA $1,104 total
includes taxes & fees
Aug 30 - Aug 31
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, (18 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
The price is CA $91
CA $234 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $160
CA $375 total
includes taxes & fees
Sep 13 - Sep 14
Bluebird Cottage
A single-story house with a blue exterior, a chimney, and a large windowed porch.

4. Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail
Roseland
8.8 out of 10, Excellent, (13 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 $426 total
includes taxes & fees
Sep 13 - Sep 14
Bluebird Cottage: Near 151 + Appalachian Trail
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 CA $378
CA $900 total
includes taxes & fees
Sep 1 - Sep 2
Modern Nellysford Getaway on 40 Private Acres!
A wooden deck with a round table and chairs, a grill, and a trash can.

6. 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.
The price is CA $217
CA $467 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.

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

Artisan's Cottage: Woodsy+Private, Central to 151
Afton
The price is CA $165
CA $433 total
includes taxes & fees
Aug 31 - Sep 1
Artisan's Cottage: Woodsy+Private, Central to 151
A stone wall, a small stream, and a house with a red roof.

8. 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 $269
CA $469 total
includes taxes & fees
Sep 4 - Sep 5
Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
A rural landscape with a large house, a fenced yard, and a dirt road.

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 CA $234
CA $653 total
includes taxes & fees
Sep 3 - Sep 4
Little Haven Cottage: Walk to Meade Tasting
A rustic wooden cabin with a porch, surrounded by dense foliage and a stone pathway.

10. 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 CA $216
CA $405 total
includes taxes & fees
Aug 30 - Aug 31
Unique Cypress cottage, close to Charlottesville with mountain views.
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)
"Clean, new, easy and practical. Very pretty wooded site. Will stay again."
United States
Daniel G.
The price is CA $239
CA $308 total
includes taxes & fees
Sep 1 - Sep 2
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
A single-story house with a green exterior and a white porch.

12. 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)
"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 $464 total
includes taxes & fees
Sep 22 - Sep 23
High Street | Walk to Everything Crozet | Pet-Friendly
A house surrounded by trees with a clear sky.

13. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is CA $165
CA $381 total
includes taxes & fees
Aug 31 - Sep 1
Artisan's Cottage
A two-story white house with a front porch, a staircase, and a small front yard.

14. 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 $229
CA $513 total
includes taxes & fees
Sep 14 - Sep 15
Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
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 $209
CA $346 total
includes taxes & fees
Aug 30 - Aug 31
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. Classic Virginia Cottage, 10 min to UVA and Vineyards

Classic Virginia Cottage, 10 min to UVA and Vineyards
Charlottesville
The price is CA $585
CA $796 total
includes taxes & fees
Sep 20 - Sep 21
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.

17. 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 $514
CA $699 total
includes taxes & fees
Aug 31 - Sep 1
Dog Friendly Cottage Close to UVA
A residential area with houses featuring gabled roofs and stone exteriors, surrounded by trees and a mountain backdrop.

18. 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 CA $609
CA $832 total
includes taxes & fees
Sep 20 - Sep 21
Charming Cottage Near Vineyards
A two-story house with a wooden deck and a stone border.

19. Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
The price is CA $234
CA $574 total
includes taxes & fees
Sep 3 - Sep 4
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 Built Designer Home in Wintergreen

Newly Built Designer Home in Wintergreen

10/10 Excellent
"This is one of the finest properties we've ever visited in all of our trips to Wintergreen. We have been coming since 1978. The location is great. It's snuggled into the lower elevations of the resort. That will pay dividends during your stay. Less vehicular and foot traffic. Combine that with easy access to the Appalachian Trail for some of the best hiking and views in the Blue Ridge. Ideal for kids and pets.The property itself? Beautiful, clean, tasteful, accommodating. The lighting and furnishings are designer quality. The well stocked kitchen is a joy to use with all of the necessary gadgets and utensils. Prefer pour over coffee? Your goose neck kettle is waiting. More of a French press kind of person? The Fellow Clara press is ready to go.The bedrooms and bathrooms are beautifully appointed. The wifi and entertainment setup are top drawer. You will not be disappointed. Highly recommended!"
Michael L. 7-night trip
Posted 19 hours ago
Newly Built Designer Home in Wintergreen

Find out more about Wintergreen

Wintergreen Cottages information

Number of reviews
291
Accommodation
34 Cottages
Lowest Price
CA $234
Highest Price
CA $1,104

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