Top Chalets in Rockbridge County in 2026

A mountainous landscape with pine trees and rocky terrain.

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Our top choices for Rockbridge 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

Chestnut Springs

Karen N.

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

Deer Springs

Chris R.

HK$7,338 total

includes taxes & fees

19 Oct - 20 Oct

A multi-story wooden house with a balcony, surrounded by trees and set on a hillside.

3. Wintergreen Luxury, Best Views in VA!

Wintergreen Resort

Emily L.

A mountain lodge with multiple roofs, surrounded by dense forest and distant mountain ranges.

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

Wintergreen Resort

A two-story cabin with a balcony, surrounded by trees.

5. Majestic Mtn Cabin w quick hiking & overlook access

Nellysford

Suzanie

A cabin with a wooden staircase leading to a deck, surrounded by trees and a gravel path.

6. NEW! The Nest Treehouse near Goshen Pass

Rockbridge Baths

Lyndsay R.

A patio with Adirondack chairs and a fire pit, overlooking a grassy field and forested hills.

7. Secluded Mountain Cabin Firepit 12ppl

Lovingston

Mary A.

A cabin with a stone foundation, wooden deck, and large windows.

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

Wintergreen Resort

Mary

A hot tub with a wooden deck and a scenic view of mountains and trees.

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

Vesuvius

Craig N.

HK$5,518 total

includes taxes & fees

18 Oct - 19 Oct

A cabin with a wooden deck and a snow-covered roof, surrounded by trees.

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

Treeloft

A wooden deck with wicker furniture and a glass-top table, overlooking a forested area.

11. 2min to Ski! DogsOK Wood Stove Grill Fire Pit Hike

Wintergreen Resort

Fred T.

A wooden deck with a railing and a single wooden chair.

12. Sleepy Bear Chalet

Roseland

"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. "

Marisa I.

A two-story cabin with a porch, surrounded by greenery and a mountain view.

13. Elk Mountain Overlook: Breathtaking Views

Afton

Margaret

HK$5,966 total

includes taxes & fees

31 Oct - 1 Nov

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

Nellysford

Alyssa A.

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Top Rockbridge County Hotel Reviews

Holiday Inn Express & Suites Waynesboro East by IHG

10/10 Excellent

"We didn’t like paying to park…. We didn’t know we had to until we checked out. Thank goodness the young lady mentioned it to us as we were checking out!! Rooms cost enough with the rate and taxes!"