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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Browse Select Wintergreen Cottages

Serene Roseland Retreat Near Wintergreen Resort!
House (3 Bedrooms) | Front of property

Serene Roseland Retreat Near Wintergreen Resort!

3.0 star property
Serene Roseland Retreat Near Wintergreen Resort!
Grand Chalet w/ Hot Tub - Near Wintergreen Resort
House (4 Bedrooms) | Front of property

Grand Chalet w/ Hot Tub - Near Wintergreen Resort

3.0 star property
10.0 out of 10, Exceptional, (1)
"The Shamokin Chalet (Grand Chalet) was a gorgeous home with amazing mountain views! It was one of the most well appointed homes I’ve stayed in - well stocked kitchen (paper products, spices, dishes, cooking supplies, coffees), shampoos, conditioners, body wash, toilet paper and plenty of towels in all bathrooms, even beach towels for the hot tub. The home was beautifully decorated and immaculate. The landscaping was gorgeous. It had the most massive TV I’ve ever seen. The owner was a great...
Grand Chalet w/ Hot Tub - Near Wintergreen Resort
Wintergreen Resort Home w/ 2 Decks + Ski Access!
House (3 Bedrooms) | Interior

Wintergreen Resort Home w/ 2 Decks + Ski Access!

3.0 star property
Wintergreen Resort Home w/ 2 Decks + Ski Access!
Cozy 'hillside Hideaway' in Wintergreen Resort!
Interior

Cozy 'hillside Hideaway' in Wintergreen Resort!

3.0 star property
Cozy 'hillside Hideaway' in Wintergreen Resort!
Spacious Home: 10 Miles to Wintergreen Resort!
House (3 Bedrooms) | Interior

Spacious Home: 10 Miles to Wintergreen Resort!

3.0 star property
Spacious Home: 10 Miles to Wintergreen Resort!
Yogis Paradise w/ Deck ~ 1 Mi to Yogaville!
House (4 Bedrooms) | Interior

Yogis Paradise w/ Deck ~ 1 Mi to Yogaville!

3.0 star property
Yogis Paradise w/ Deck ~ 1 Mi to Yogaville!
Modern Nellysford Getaway on 40 Private Acres!
House (3 Bedrooms) | Interior

Modern Nellysford Getaway on 40 Private Acres!

3.0 star property
The price is 7.116.660 ₫
15.140.562 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Modern Nellysford Getaway on 40 Private Acres!
Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit
House (2 Bedrooms) | Interior

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

3.0 star property
9.0 out of 10, Wonderful, (2)
"Very quiet and restful place to spend a little time"
Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit
Golf Course-view Cabin: Deck in Wintergreen Resort
House (3 Bedrooms) | Interior

Golf Course-view Cabin: Deck in Wintergreen Resort

3.0 star property
Golf Course-view Cabin: Deck in Wintergreen Resort
Cozy 'nonny Cottage' Near Appalachian Trail!
Cottage (2 Bedrooms) | Interior

Cozy 'nonny Cottage' Near Appalachian Trail!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a quiet, beautiful weekend. The cottage was just what we needed to unplug as a family and just enjoy nature and each other. This cottage provided ample space for the whole family including a big yard with lots of space for the kids to run and play. It was clean and tidy. We are thankful and would stay here again."
Cozy 'nonny Cottage' Near Appalachian Trail!
Peaceful Raphine Cottage w/ Deck & Fireplace!
Interior

Peaceful Raphine Cottage w/ Deck & Fireplace!

3.0 star property
Peaceful Raphine Cottage w/ Deck & Fireplace!
Wintergreen Home w/ Deck - Near Skiing & Hiking!
Interior

Wintergreen Home w/ Deck - Near Skiing & Hiking!

3.0 star property
Wintergreen Home w/ Deck - Near Skiing & Hiking!
Lyndhurst Cabin on Farm w/ Pond & Stocked Stream!
House (1 Bedroom) | Interior

Lyndhurst Cabin on Farm w/ Pond & Stocked Stream!

3.0 star property
Lyndhurst Cabin on Farm w/ Pond & Stocked Stream!
Wintergreen Resort Home ~ 2 Miles to Ski Slopes!
Interior

Wintergreen Resort Home ~ 2 Miles to Ski Slopes!

3.0 star property
Wintergreen Resort Home ~ 2 Miles to Ski Slopes!
Stunning Wintergreen Resort Home: Ski & Golf!
House (4 Bedrooms) | Interior

Stunning Wintergreen Resort Home: Ski & Golf!

3.0 star property
Stunning Wintergreen Resort Home: Ski & Golf!
Charming Cottage < 10 Mi to Wineries & Skiing!
Cottage (2 Bedrooms) | Interior

Charming Cottage < 10 Mi to Wineries & Skiing!

3.0 star property
Charming Cottage < 10 Mi to Wineries & Skiing!
Historic Staunton Home ~ 1 Mi to Downtown!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Historic Staunton Home ~ 1 Mi to Downtown!

3.0 star property
Historic Staunton Home ~ 1 Mi to Downtown!
Cozy Wintergreen Cabin Near Mountain Inn & Slopes!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Cozy Wintergreen Cabin Near Mountain Inn & Slopes!

3.0 star property
10.0 out of 10, Exceptional, (1)
Cozy Wintergreen Cabin Near Mountain Inn & Slopes!
Wintergreen Resort Cabin: Near the Slopes!
House (3 Bedrooms) | Interior

Wintergreen Resort Cabin: Near the Slopes!

3.0 star property
Wintergreen Resort Cabin: Near the Slopes!
Wintergreen Resort Home w/ Deck, 1 Mi to Skiing!
House (3 Bedrooms) | Interior

Wintergreen Resort Home w/ Deck, 1 Mi to Skiing!

3.0 star property
Wintergreen Resort Home w/ Deck, 1 Mi to Skiing!
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

Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG

10/10 Excellent
"Great staff and facilities."
Robert 4-night trip
Posted 23 hours ago
Holiday Inn Express & Suites Waynesboro East by IHG

Frequently asked questions

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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.