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
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Wintergreen cottages

Outdoor dining

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.
Mountain Mindset: Pup Friendly + Trail
Cottage, Private Bathroom (Bluebird Cottage) | Exterior

Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is AU$385
includes taxes & fees
20 July - 21 July
Bluebird Cottage
Exterior

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.4 out of 10, Exceptional, (15 reviews)
"The property was very clean and awesome! It met the needs of our 2 day stay with our pets. We would stay again!"
United States
Joni K.
The price is AU$261
includes taxes & fees
2 Aug - 3 Aug
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
House (3 Bedrooms) | Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is AU$869
includes taxes & fees
7 Aug - 8 Aug
Modern Nellysford Getaway on 40 Private Acres!
Terrace/patio

Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail
Roseland
8.8 out of 10, Excellent, (12 reviews)
"This house is perfect for a girls weekend. We did a couple places further out but enjoyed Bold Rock and Devils Backbone. It had everything we needed to enjoy some much needed time to relax at the house also. "
United States
Katherine N.
The price is AU$435
includes taxes & fees
20 July - 21 July
Bluebird Cottage: Near 151 + Appalachian Trail
Outdoor dining

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 AU$481
includes taxes & fees
22 July - 23 July
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Exterior

The Cottage @ Afton Mountain- Close to Wineries!

The Cottage @ Afton Mountain- Close to Wineries!
Afton
10.0 out of 10, Exceptional, (32 reviews)
"Well supplied with essentials , charming"
United States
Beth
The price is AU$456
includes taxes & fees
20 July - 21 July
The Cottage @ Afton Mountain- Close to Wineries!
Property grounds

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, (30 reviews)
"Everything was great! The house is well appointed and the fenced in yard was perfect for our dogs. Highly recommend."
United States
Michael W.
The price is AU$486
includes taxes & fees
28 July - 29 July
Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
Exterior

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

Artisan's Cottage: Woodsy+Private, Central to 151
Afton
The price is AU$454
includes taxes & fees
20 July - 21 July
Artisan's Cottage: Woodsy+Private, Central to 151
Exterior

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 AU$630
includes taxes & fees
30 July - 31 July
Little Haven Cottage: Walk to Meade Tasting
Exterior

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, (60 reviews)
"We have stayed here once before and we absolutely love the place. Mary is an excellent host and she did everything to accommodate us. "
United States
Kurt K.
The price is AU$427
includes taxes & fees
3 Aug - 4 Aug
Unique Cypress cottage, close to Charlottesville with mountain views.
Cottage, Private Bathroom (Basecamp Cottage) | Exterior

Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
The price is AU$556
includes taxes & fees
21 July - 22 July
Little Haven Cottage
Exterior

High Street | Walk to Everything Crozet | Pet-Friendly

High Street | Walk to Everything Crozet | Pet-Friendly
Crozet
9.8 out of 10, Exceptional, (110 reviews)
"Great little spot, very close to “downtown” Crozet. Great host, great communication…."
United States
Anonymous traveller
The price is AU$465
includes taxes & fees
28 July - 29 July
High Street | Walk to Everything Crozet | Pet-Friendly
Exterior

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

Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
Charlottesville
The price is AU$532
includes taxes & fees
10 Aug - 11 Aug
Family-Friendly Cottage 2BR + Loft - Fire Pit, Near UVA, Hiking & Wineries
Exterior

Petite Pink Cottage, Perfect for Solo Travelers

Petite Pink Cottage, Perfect for Solo Travelers
Charlottesville
10.0 out of 10, Exceptional, (9 reviews)
"We loved staying here, it was super cozy and comfortable, the perfect place to stay for a visit to Charlottesville. We'll definitely be back!"
United States
Peter S.
The price is AU$592
includes taxes & fees
19 July - 20 July
Petite Pink Cottage, Perfect for Solo Travelers
Exterior

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 AU$699
includes taxes & fees
18 July - 19 July
Dog Friendly Cottage Close to UVA
Exterior

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

Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
Charlottesville
8.8 out of 10, Excellent, (5 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 AU$306
includes taxes & fees
11 Aug - 12 Aug
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
Exterior

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 AU$358
includes taxes & fees
9 Aug - 10 Aug
The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
Cottage, Private Bathroom (Artisan's Cottage) | Exterior

Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is AU$401
includes taxes & fees
20 July - 21 July
Artisan's 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

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

10/10 Excellent
"Beautiful view! The condo was very cleanAnd check in was easy."
Frank S. 2-night trip
Posted 3 days ago
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Find out more about Wintergreen

Wintergreen Cottages information

Number of reviews
297
Accommodation
34 Cottages
Lowest Price
AU$261
Highest Price
AU$869

Frequently asked questions

What is there to do in Wintergreen near my cottage?
The most useful travel accessory is a well-thought-out travel plan. Bold Rock Hard Cider Nellysford Cidery is a great place to kick-start your adventures in Wintergreen.