Lodging Image

Chalets in Waynesboro City County

Compare and save

  • 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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Waynesboro City County chalets

A large, two-story house with multiple decks and a spacious front porch, surrounded by dense forest.

1. Fully Loaded 8BR in Wintergreen! Sleeps 23

Fully Loaded 8BR in Wintergreen! Sleeps 23
Chestnut Springs
10.0 out of 10, Exceptional, (15 reviews)
"Excellent amenities and host was attentive. Great place to stay with a large group. "
United States
Karen N.
Fully Loaded 8BR in Wintergreen! Sleeps 23
A two-story wooden cabin with a balcony, string lights, and a visible interior with a bed and seating area.

2. Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16

Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16
Deer Springs
10.0 out of 10, Exceptional, (11 reviews)
"It's a nice house, and check in/out was super easy."
United States
Chris R.
The price is CA $608
CA $1,368 total
includes taxes & fees
Oct 14 - Oct 15
Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16
A multi-story wooden house with a balcony, surrounded by trees and set on a hillside.

3. Wintergreen Luxury, Best Views in VA!

Wintergreen Luxury, Best Views in VA!
Wintergreen Resort
10.0 out of 10, Exceptional, (45 reviews)
"This house was beautiful and had so much to offer. Great communication."
United States
Emily L.
Wintergreen Luxury, Best Views in VA!
A mountain lodge with multiple roofs, surrounded by dense forest and distant mountain ranges.

4. Dragon's Back, 9BR 10BA in Wintergreen

Dragon's Back, 9BR 10BA in Wintergreen
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"A fabulous host: super responsive when we had questions and sent a comprehensive guide book ahead of time which helped us plan the trip."
United States
Brooke S.
Dragon's Back, 9BR 10BA in Wintergreen
A two-story cabin with a balcony, surrounded by trees.

5. Majestic Mtn Cabin w quick hiking & overlook access

Majestic Mtn Cabin w quick hiking & overlook access
Nellysford
10.0 out of 10, Exceptional, (5 reviews)
Majestic Mtn Cabin w quick hiking & overlook access
A patio with Adirondack chairs and a fire pit, overlooking a grassy field and forested hills.

6. Secluded Mountain Cabin Firepit 12ppl

Secluded Mountain Cabin Firepit 12ppl
Lovingston
9.4 out of 10, Exceptional, (6 reviews)
"The host was very responsive to all of my requests."
United States
Mary A.
Secluded Mountain Cabin Firepit 12ppl
A cabin with a stone foundation, wooden deck, and large windows.

7. Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.

Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.
Wintergreen Resort
10.0 out of 10, Exceptional, (123 reviews)
"This property was beautiful, well stocked and very cozy!"
United States
Mary
Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.
A hot tub with a wooden deck and a scenic view of mountains and trees.

8. Luxury Mountain Lodge: Hot Tub and Incredible Mountain Views

Luxury Mountain Lodge: Hot Tub and Incredible Mountain Views
Vesuvius
10.0 out of 10, Exceptional, (21 reviews)
"Great view and great location! We loved it."
United States
Craig N.
The price is CA $513
CA $1,004 total
includes taxes & fees
Oct 18 - Oct 19
Luxury Mountain Lodge: Hot Tub and Incredible Mountain Views
A cabin with a wooden deck and a snow-covered roof, surrounded by trees.

9. Luxury Ski-in/Ski-out Chalet with Mountain Views at Wintergreen Resort

Luxury Ski-in/Ski-out Chalet with Mountain Views at Wintergreen Resort
Treeloft
10.0 out of 10, Exceptional, (8 reviews)
"We loved our time here. Great location for ski in/out and the amenities are excellent. Host was easily accessible and would love to stay here again. "
United States
tim f.
Luxury Ski-in/Ski-out Chalet with Mountain Views at Wintergreen Resort
A wooden deck with wicker furniture and a glass-top table, overlooking a forested area.

10. 2min to Ski! DogsOK Wood Stove Grill Fire Pit Hike

2min to Ski! DogsOK Wood Stove Grill Fire Pit Hike
Wintergreen Resort
9.4 out of 10, Exceptional, (11 reviews)
2min to Ski! DogsOK Wood Stove Grill Fire Pit Hike
A wooden deck with a railing and a single wooden chair.

11. Sleepy Bear Chalet

Sleepy Bear Chalet
Roseland
8.6 out of 10, Excellent, (4 reviews)
"The location was great for a ski vacation - an easy walk to the main lodge even with kids.The property itself is dated and could use a number of upgrades. Very basic amenities and light blankets on the beds - would definitely recommend bringing extra blankets (and towels) if you plan to stay for a cold weekend. The listing noted that there is access to an indoor pool which we found out was not the case and the property does not have resort access. "
United States
Marisa I.
Sleepy Bear Chalet
A spa building with a sign reading "The Spa at Wintergreen."

12. Wintergreen Ridge Retreat

Wintergreen Ridge Retreat
Chestnut Springs
7.8 out of 10, Good, (8 reviews)
"Nice house and great location. We checked out several breweries and cideries. Took nice drive along the Blue Ridge Parkway. "
United States
Teresa H.
Wintergreen Ridge Retreat
A two-story cabin with a porch, surrounded by greenery and a mountain view.

13. Elk Mountain Overlook: Breathtaking Views

Elk Mountain Overlook: Breathtaking Views
Afton
9.0 out of 10, Wonderful, (8 reviews)
"Well equipped Cabin with amazing views"
United States
Margaret
The price is CA $433
CA $828 total
includes taxes & fees
Oct 14 - Oct 15
Elk Mountain Overlook: Breathtaking Views
A two-story house with a front porch, wooden stairs, and a small garden area.

14. Opulent Retreat Amidst Blue Ridge`s Serenity * Dog Friendly * Hot Tub

Opulent Retreat Amidst Blue Ridge`s Serenity * Dog Friendly * Hot Tub
Nellysford
10.0 out of 10, Exceptional, (10 reviews)
"Just like the pictures, don't hesitate! Just book!!"
United States
Alyssa A.
Opulent Retreat Amidst Blue Ridge`s Serenity * Dog Friendly * Hot Tub
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Waynesboro City County Hotel Reviews

The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

8/10 Good
"Our stay at Blackburn Inn was one to be remembered with all the history it holds. The room was clean and comfortable but the breakfast, for the type hotel, does not equate. If you stay here, and I recommend you do, go elsewhere for breakfast. It's more like a contential breakfast served at your table. They had run out of napkins so we got brown "service station" paper towels after the silverware was placed on the naked table. The eggs (over medium, scrambled) were cooked to brown and the belgian waffles were nothing more than small, square Eggos. The waiter however, was very nice and knowledgeable about the hotel and the area and offered sites to see and things to do. Don't let the breakfast keep you from visiting The Blackburn Inn."
Robin 2-night trip
Posted 3 hours ago
The Blackburn Inn and Conference Center

Find out more about Waynesboro City County

Waynesboro City County Chalets information

Number of reviews
252
Accommodation
14 Chalets
Lowest Price
CA $828
Highest Price
CA $1,368

Explore a world of travel with Expedia