Photo by Rebecca Brent

Wintergreen Vacation Rentals

Vacation Rentals in Wintergreen

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
Terrace/patio
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
9.6 out of 10, Exceptional, 264 reviews
"We had a great time. The house was comfortable and the area is beautiful! The only issues we had were a humming of the fan in the master bedroom upstairs, the door lock didn’t work for us (but the owners helped with this and all was well), and we had a hard time finding where to dump trash. The hot tub was wonderful, the wifi works great (we had one doing online school and one work), and all was just as the listing described. It was a great place to stay for a Liberty University graduation. If...
The price is $179
$414 total
includes taxes & fees
Jun 6 - Jun 7
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV 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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Walk to Mtn Inn & The Market
Living area | Smart TV, fireplace, books
Walk to Mtn Inn & The Market
9.6 out of 10, Exceptional, 19 reviews
"It was nice. We discovered that the property was for sale which might have caused the kitchen to be short on utensils. We prefer to cook most meals when vacationing due to individual diets. Otherwise, allwas ok and I would feelfree to recommend it. Ann"
Walk to Mtn Inn & The Market
Ski-In/Ski-Out Comfy Condo
Private kitchen
Ski-In/Ski-Out Comfy Condo
10.0 out of 10, Exceptional, 11 reviews
"Our stay was great. We had a issue with the door when we we arrived But I called Alicja and we were able to fix it over the phone. The only complaint I would have is you can hear the people in the condo above us walking around and they were up at 6:00AM every morning. Can't control other people. Overall very happy with our stay"
Ski-In/Ski-Out Comfy Condo
Fantastic Mountain & Valley Views! On Top of the Mountain & Close to the Resort.
Fridge, microwave, oven, stovetop
Fantastic Mountain & Valley Views! On Top of the Mountain & Close to the Resort.
9.8 out of 10, Exceptional, 164 reviews
"The house is very cute and clean, the mountains view is stunning!"
Fantastic Mountain & Valley Views! On Top of the Mountain & Close to the Resort.
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
Pine Cottage: Hot Tub and Central to Nelson 151
Property grounds
Pine Cottage: Hot Tub and Central to Nelson 151
10.0 out of 10, Exceptional, 14 reviews
"Need to step back and regroup and refresh and the cottage was perfect. Quiet, hot tub under the stars and a good night sleep was what the dr ordered !! Thank you!!"
The price is $199
$465 total
includes taxes & fees
Jun 6 - Jun 7
Pine Cottage: Hot Tub and Central to Nelson 151
Blue Ridge Mountain Retreat in Wintergreen
Golf
Blue Ridge Mountain Retreat in Wintergreen
9.2 out of 10, Wonderful, 59 reviews
"I brought a group of 20 youth and adults for a church ski retreat. The house was comfortable, fully stocked with the necessities and easily accessible to Wintergreen"
Blue Ridge Mountain Retreat in Wintergreen
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Property grounds
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
9.8 out of 10, Exceptional, 11 reviews
"We enjoyed our stay at Travelers' Rest but I think the listing should mention that the upstairs bedroom is a loft and open to the LR (which did not work with an early rising infant). Also, and I should know by now, the photos make the living area look bigger than it is. That said, it is wonderfully situated at end of cul de sac but close to lodge and market. The view is spectacular and it is very well equipped."
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Outdoor dining
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
10.0 out of 10, Exceptional, 107 reviews
"There was an issue upon arrival, however the owners stepped right up to fix it. The house is very comfortable for 4 adults and 2 children. My only difficulty was the outside stairs. For an older couple the coolers were very heavy when we made it to the top :-) All in all, we had an enjoyable stay. Be alert as we had our truck broken into by a bear. No damage done, but a lesson learned."
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Valley Extended Suites
Standard Suite | Private kitchen | Full-size fridge, microwave, oven, stovetop
Valley Extended Suites
3.0 star property
9.0 out of 10, Wonderful, 151 reviews
"We loved the scenic drive to the property traveling from East on 64. "
The price is $95
$106 total
includes taxes & fees
Jun 10 - Jun 11
Valley Extended Suites
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, 238 reviews
"We were very happy with our stay at this lovely place! It was a wonderful experience and we are looking forward to the next time."
The price is $99
$216 total
includes taxes & fees
Jun 6 - Jun 7
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Virginia Mountain Get Away Cabin...Hunt Fish Hike Bike
Exterior
Virginia Mountain Get Away Cabin...Hunt Fish Hike Bike
10.0 out of 10, Exceptional, 27 reviews
"Cute little cabin with great mountain views. We a great time. We will probably come back again."
Virginia Mountain Get Away Cabin...Hunt Fish Hike Bike
5 Bedroom Hilltop Villa with Hot Tub and Magnificent Views
Fridge, microwave, oven, stovetop
5 Bedroom Hilltop Villa with Hot Tub and Magnificent Views
9.8 out of 10, Exceptional, 19 reviews
"We had a fantastic time! House accommodations were exceptional. Very secluded. All needs were met. Would definitely do it again."
5 Bedroom Hilltop Villa with Hot Tub and Magnificent Views
Restored Vintage Airstream at Craft Brewery
Outdoor dining
Restored Vintage Airstream at Craft Brewery
9.6 out of 10, Exceptional, 8 reviews
"Cute, wonderful place"
Restored Vintage Airstream at Craft Brewery
Cozy Country small two bedroom home.
Property grounds
Cozy Country small two bedroom home.
10.0 out of 10, Exceptional, 7 reviews
"What we needed, close to all, will be back. REG"
The price is $135
$243 total
includes taxes & fees
Jun 13 - Jun 14
Cozy Country small two bedroom home.
Restored Double Log Cabin on 400 Mountain Acres
Dining
Restored Double Log Cabin on 400 Mountain Acres
10.0 out of 10, Exceptional, 218 reviews
"We loved the remoteness and rustic feel of the property/house! Great in accommodating our group of 12 - loved sitting on the front porch and lighting the fire pit. We were there for three nights and we did not watch the tv once - testament to how much fun we were having as a family. We also hiked and walked and visited vineyards, ciders and breweries! All in all, the property/house gave us the perfect platform and environment to have a very memorable 3 nights! Recommend without reservation,...
Restored Double Log Cabin on 400 Mountain Acres
Endless Mountain Top Views from All The Way Up!
Property grounds
Endless Mountain Top Views from All The Way Up!
10.0 out of 10, Exceptional, 34 reviews
"This is our second time staying at this condo. We just relax upon entering the door. The balcony is our sanctuary. The views are spectacular. The condo itself is also wonderful. It is clean and inviting. It doesn't lack for anything we may need. The bed is very comfortable and the towels are great. We love the location and you are sitting at the top of the mountain. There is so much to do in the area even in the summer months whether hiking or visiting wineries, breweries or distilleries among...
The price is $191
$365 total
includes taxes & fees
Jun 8 - Jun 9
Endless Mountain Top Views from All The Way Up!
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Exterior
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
10.0 out of 10, Exceptional, 220 reviews
"Bill and Cynthia are such amazing hosts and the property inside and out exemplifies it. What a great place to stay for some serious rural R&R! The property was very clean. They have thought of everything one would need for a delightful get away. If you forgot anything, just ask and they are sure to help one way or another. The Fresh eggs, courtesy of their chickens, were a treat and the farm animals are such fun…esp Posy, Zoey and Hemingway. We hope to return soon for a longer retreat! Thank you...
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
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.

Wintergreen Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
Wintergreen condos
Known landmarks
Bold Rock Hard Cider Nellysford Cidery, Hill Top Berry Farm & Winery and Stoney Creek Golf Course
International airport
Charlottesville, VA (CHO-Charlottesville-Albemarle)

Other types of properties in Wintergreen you may be interested in

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
Terrace/patio
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
9.6 out of 10, Exceptional, 264 reviews
"We had a great time. The house was comfortable and the area is beautiful! The only issues we had were a humming of the fan in the master bedroom upstairs, the door lock didn’t work for us (but the owners helped with this and all was well), and we had a hard time finding where to dump trash. The hot tub was wonderful, the wifi works great (we had one doing online school and one work), and all was just as the listing described. It was a great place to stay for a Liberty University graduation. If...
The price is $179
$414 total
includes taxes & fees
Jun 6 - Jun 7
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV 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.

Everything you need to know about Wintergreen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wintergreen vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wintergreen. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wintergreen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $95 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wintergreen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wintergreen vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wintergreen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Wintergreen?

Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip.

What are some of the best vacation rentals that Wintergreen has to offer?

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.: Visitors give good reviews to this Wintergreen vacation home rental, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a spa tub. Our travelers also rate Fantastic Mountain & Valley Views! On Top of the Mountain & Close to the Resort. as a favorite home for rent in Wintergreen.

How many vacation rentals are there in Wintergreen?

Choose from 50 Expedia vacation rentals in Wintergreen for a memorable vacation.

What can I see and do in Wintergreen?

While exploring the area, visit family-friendly sights like War Fields, or get outside and enjoy nature at George Washington National Forest. Wintergreen Resort and Bold Rock Hard Cider Nellysford Cidery are a couple of places you'll find in the larger area.

What’s a vacation rental in Wintergreen like?

A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.

Recent reviews of Wintergreen properties
Expedia verified reviews

Sleep Inn Staunton

Sleep Inn Staunton

5/5 Excellent
"Room was clean & comfortable. Enjoyed the breakfast also"
A verified traveler stayed at Sleep Inn Staunton
Posted 3 days ago
Sleep Inn Staunton