Search Wintergreen Cottage Rentals from CA $197

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Wintergreen cottages

Property grounds

Cottage in Laurel Ridge

Mountain Mindset: Pup Friendly + Trail
9.8 out of 10, Exceptional, (9 reviews)
"Gorgeous setting and incredibly cozy. Perfect for our holiday family gathering!"
United States
Calli S.
The price is CA $367
CA $1,083 total
includes taxes & fees
Mar 3 - Mar 4
Mountain Mindset: Pup Friendly + Trail
Exterior

Cottage in Charlottesville

Unique Cypress cottage, close to Charlottesville with mountain views.
10.0 out of 10, Exceptional, (48 reviews)
"We had a wonderful stay. We'll come back"
United States
Marilyn K.
The price is CA $201
CA $385 total
includes taxes & fees
Mar 3 - Mar 4
Unique Cypress cottage, close to Charlottesville with mountain views.
Terrace/patio

Cottage in Roseland

Bluebird Cottage: Near 151 + Appalachian Trail
8.4 out of 10, Very good, (9 reviews)
"Nice quiet spot. On the same property as the owners, but still felt private. I loved seeing their dogs running in their yard every time we drove by I highly recommend the great goes that are nearby, as well as Bold Rock and Devils Backbone Brewery!"
United States
Amanda D.
The price is CA $157
CA $398 total
includes taxes & fees
Mar 3 - Mar 4
Bluebird Cottage: Near 151 + Appalachian Trail
Exterior

Cottage in Afton

Brand new serene luxury cottage just off the Brew Ridge Trail
10.0 out of 10, Exceptional, (5 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 CA $87
CA $197 total
includes taxes & fees
Mar 8 - Mar 9
Brand new serene luxury cottage just off the Brew Ridge Trail
Exterior

Cottage in Crozet

High Street | Walk to Everything Crozet | Pet-Friendly
9.8 out of 10, Exceptional, (105 reviews)
"Such a lovely cottage in a great spot!We enjoyed Crozet and time at Praha bakery, Star Hill Brewery, King Family Vineyard, and Mint Springs Park!"
United States
Polly H.
The price is CA $273
CA $459 total
includes taxes & fees
Mar 8 - Mar 9
High Street | Walk to Everything Crozet | Pet-Friendly
Exterior

Cottage in Afton

The Cottage @ Afton Mountain- Close to Wineries!
10.0 out of 10, Exceptional, (22 reviews)
"Yes, Cottage amenities adequate "
United States
CARL W.
The price is CA $198
CA $436 total
includes taxes & fees
Mar 4 - Mar 5
The Cottage @ Afton Mountain- Close to Wineries!
Outdoor dining

Cottage in Afton

Afton Cottage w/ Hot Tub, Firepit, Mountain Views
10.0 out of 10, Exceptional, (12 reviews)
"Very tranquil place. "
United States
Thomas K.
The price is CA $187
CA $440 total
includes taxes & fees
Mar 5 - Mar 6
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Exterior

Cottage in Staunton

The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
10.0 out of 10, Exceptional, (1 review)
"Beautiful grounds and views. Pet friendly in some suites the cottage"
United States
Carina
The price is CA $205
CA $341 total
includes taxes & fees
Mar 4 - Mar 5
The Cottage at Batten Green, Beautiful Farm Views, 5 mins to DT Staunton, Pet-Friendly!
Exterior

Cottage in Crozet

Rosé All Day: Wine Country Getaway! Walk to Dining
10.0 out of 10, Exceptional, (20 reviews)
"great area and location for quiet, peaceful vacation with lots of active things to do within 30-45 minute drives in all directions."
United States
Matthew L.
The price is CA $176
CA $451 total
includes taxes & fees
Mar 3 - Mar 4
Rosé All Day: Wine Country Getaway! Walk to Dining
Exterior

Cottage in Charlottesville

Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
The price is CA $226
CA $290 total
includes taxes & fees
Mar 3 - Mar 4
Wandering Bear’s Cottage Near Crozet & Charlottesville, 2 bedroom
1 bedroom, free WiFi, bed sheets, wheelchair access

Cottage in Charlottesville

Pet-Friendly Kent Cottage at Ivy Cottages
10.0 out of 10, Exceptional, (6 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 CA $409
CA $799 total
includes taxes & fees
Mar 3 - Mar 4
Pet-Friendly Kent Cottage at Ivy Cottages
Exterior detail

Cottage in Afton

Peaceful 2-bedroom cottage with AC in charming Afton
The price is CA $327
CA $505 total
includes taxes & fees
Mar 3 - Mar 4
Peaceful 2-bedroom cottage with AC in charming Afton
Outdoor dining

Cottage in Afton

Little Haven Cottage: Walk to Meade Tasting
The price is CA $231
CA $610 total
includes taxes & fees
Mar 3 - Mar 4
Little Haven Cottage: Walk to Meade Tasting
House (3 Bedrooms) | Interior

Cottage in Nellysford

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
The price is CA $334
CA $830 total
includes taxes & fees
Mar 24 - Mar 25
Modern Nellysford Getaway on 40 Private Acres!
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.
View all properties

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Wintergreen Hotel Reviews

The Modern Mountain Condo

The Modern Mountain Condo

10/10 Excellent
"Great place for a quick trip with a small to medium sized family!! Plenty of sleeping spots despite only 1BR"
Dennis M. 3-night trip
Posted 6 days ago
The Modern Mountain Condo

Find out more about Wintergreen

Wintergreen Cottages information

Number of reviews
237
Accommodation
34 Cottages
Lowest Price
CA $197
Highest Price
CA $1,083

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.

Explore a world of travel with Expedia