Photo by Rebecca Brent

Search Chalets in Wintergreen

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Chalets in Wintergreen

2min to Ski! DogsOK+Wood Stove+Grill+Fire Pit+Hike
Fridge, microwave, oven, stovetop
2min to Ski! DogsOK+Wood Stove+Grill+Fire Pit+Hike
10.0 out of 10, Exceptional, 1 review
"We booked this getaway on a whim and wasn’t quite sure what to expect, but the property and location was the PERFECT spot for our family of four, plus a family friend. The wood interior of the cabin is gorgeous and had all the perfect touches to make us feel right at home. All the information we needed was provided without asking and everything was a breeze. We had such a great time. 10/10! Would recommend and plan to book again!"
2min to Ski! DogsOK+Wood Stove+Grill+Fire Pit+Hike
Luxury Chalet, Best Views in Virginia
Property grounds
Luxury Chalet, Best Views in Virginia
10.0 out of 10, Exceptional, 25 reviews
"We had a fabulous time at Blackrock Manor to celebrate a 90th birthday. The house works well for an elderly person as no steps are required to enter the house and the primary bedroom is located on the main level. The house is very nice, beautifully decorated, nicely equipped but the real show stopper are the views from the huge rear decks! Absolutely stunning!"
Luxury Chalet, Best Views in Virginia
Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.
Interior
Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.
10.0 out of 10, Exceptional, 106 reviews
"Our family had a restful, wonderful time in this chalet. It was comfortable, well-appointed and clean. There was plenty of parking for our 3 small SUVs & we could have squeezed in one more. We loved the wrap-around deck with gas grill, fire-pit, and tiki torches…made for great memories!"
Spectacular Ski Chalet, 3 BR, 2.5 Bath, Great Location.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Epic Mountain Views, Hot Tub and Privacy at Harvest Moon Lodge and Retreat!
Property grounds
Epic Mountain Views, Hot Tub and Privacy at Harvest Moon Lodge and Retreat!
10.0 out of 10, Exceptional, 10 reviews
"We had a wonderful time at the Harvest Moon. Good location for a mountain getaway. The house is decorated nicely and is cozy. Basement is a plus with the pool table, air hockey and hot tub. The owners were easy to reach and answered all my questions in a timely manner. I hope to go again one day!"
The price is NZ$995
per night
17 Jun - 18 Jun
Epic Mountain Views, Hot Tub and Privacy at Harvest Moon Lodge and Retreat!
Majestic Mtn Cabin + Quick hiking trail access & wedding overlook
Living area
Majestic Mtn Cabin + Quick hiking trail access & wedding overlook
Majestic Mtn Cabin + Quick hiking trail access & wedding overlook
⭐Ski Lover's Delight⭐ | 5 Min to Slopes | Parking x4 | Cozy Fire!
Smart TV, fireplace, table football, books
⭐Ski Lover's Delight⭐ | 5 Min to Slopes | Parking x4 | Cozy Fire!
10.0 out of 10, Exceptional, 3 reviews
"Great family Property, we loved this house. Great communication with the owner. Clean and well maintained. Perfect for family with children. We will revisit in the future."
The price is NZ$811
per night
17 Jun - 18 Jun
⭐Ski Lover's Delight⭐ | 5 Min to Slopes | Parking x4 | Cozy Fire!
Opulent Retreat Amidst Blue Ridge's Serenity * Dog Friendly * Hot Tub
Smart TV, fireplace, video games, books
Opulent Retreat Amidst Blue Ridge's Serenity * Dog Friendly * Hot Tub
10.0 out of 10, Exceptional, 8 reviews
"Property was as advertised and well equipped. Driveway is kind of steep, beware if you have a low riding vehicle. We would stay there again. Convenient to Blue Ridge Parkway and wineries. Highly recommend Hazy Mountain, it is beautiful."
Opulent Retreat Amidst Blue Ridge's Serenity * Dog Friendly * Hot Tub
3min to Ski: Hot Tub+EV Charger+GoldenTee+Gig WiFi
Exterior
3min to Ski: Hot Tub+EV Charger+GoldenTee+Gig WiFi
9.0 out of 10, Wonderful, 2 reviews
"We live locally but had friends and family coming to town for my birthday so we rented Riley’s retreat. Our weekend was filled with visits to all the food and beverages on 151. I loved the fun amenities at the house ( hot tub, pool table, games, etc). My initial investigation I didn’t realize we we so far up Wintergreen but in the end it did not matter and was a perfect house for the weekend ! Thank you !!"
3min to Ski: Hot Tub+EV Charger+GoldenTee+Gig WiFi
3min to Ski: Hot Tub+EV Charger+GoldenTee+Gig WiFi
Exterior
3min to Ski: Hot Tub+EV Charger+GoldenTee+Gig WiFi
10.0 out of 10, Exceptional, 1 review
"This property was great for a weekend girls trip! We had a group of 13 and it comfortably accommodated us all! It was also a great location to the 151 Brew trail and the house had everything we needed. The only thing was the driveway was a little tight for a large vehicle."
3min to Ski: Hot Tub+EV Charger+GoldenTee+Gig WiFi
Sleepy Bear Chalet
Property grounds
Sleepy Bear Chalet
8.0 out of 10, Very good, 1 review
"The property was overall nice with minor issues. It had a funky smell upon entering, most likely due to moisture and several outlets were not working. Access to the property was very difficult for my mother with mobility issues since it went down wooden stairs that were slippery after the rain. The third bedroom is a loft with no privacy (door or enclosed walls) and due to the vaulted ceiling adults can’t comfortably be up there. "
Sleepy Bear Chalet
Modern Mountain Chalet: Hot Tub, Sauna, Gameroom, Family-Friendly Amenities
Property grounds
Modern Mountain Chalet: Hot Tub, Sauna, Gameroom, Family-Friendly Amenities
The price is NZ$1,774
per night
24 Jun - 25 Jun
Modern Mountain Chalet: Hot Tub, Sauna, Gameroom, Family-Friendly Amenities
Elk Mountain Overlook: Breathtaking Views
Interior
Elk Mountain Overlook: Breathtaking Views
Elk Mountain Overlook: Breathtaking Views
Don't see what you're looking for?
See all available properties in Wintergreen
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.

Other property types in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Terrace/patio
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
9.6 out of 10, Exceptional, 266 reviews
"Great place to chill out and breathe some cool mountain air"
The price is NZ$654
per night
24 Jun - 25 Jun
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
Outdoor dining
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
10.0 out of 10, Exceptional, 209 reviews
"This is at least the third time we have stayed in this condo unit in the last two years. There is a reason we keep coming back; it is absolutely beautiful, both the accommodations and Mountain Views. I highly recommend!"
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, 272 reviews
"We thoroughly enjoyed our stay at this condo. Quiet neighborhood and very comfortable. Appreciated all the basics offered that other rentals do not such as soap, garbage bags, toilet paper. But the owners went above that and had lotions, specialty soaps, cleaning supplies etc. Well stocked kitchen for cooking. While it was just the two of us we liked that there were games available for families and there was a nook upstairs for kids to get away. Highly recommend and would definitely come visit...
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
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.

Wintergreen Chalets information

Number of reviews
157
Accommodation
12 Chalets
Lowest Price
NZ$811
Highest Price
NZ$1,774

Recent Reviews in Wintergreen
Expedia verified reviews

Hotel 24 South

Hotel 24 South

5/5 Excellent
"Enjoyed!"
A verified traveller stayed at Hotel 24 South
Posted 21 hours ago
Hotel 24 South