Photo by Rebecca Brent

Wintergreen Vacation Rentals

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Vacation Rentals in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (294)
"Perfect ski weekend rental. Great communication with Scott. Kitchen is nicely equipped. Hot tub is hot and was perfect for soaking and relaxing after a great day of skiing."
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (309)
"Clean, cozy,and convenient!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Condo -Steps to Ski and restaurants

9.8 out of 10, Exceptional, (10)
"Perfect location. Easy to walk to the resort. Clean, cozy, and quiet. Thanks for a great stay!"
The price is CA $137
CA $340 total
includes taxes & fees
Mar 18 - Mar 19
Wintergreen Condo -Steps to Ski and restaurants

Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!

10.0 out of 10, Exceptional, (233)
"Clean, well maintained, phenomenal views. Comfy beds, lots of blankets, and pillows. We will definitely book again!"
Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

10.0 out of 10, Exceptional, (130)
"We enjoyed our stay. The kids loved being able to hit the slopes across the street. The house was well stocked and clean. Loved the mudroom and hot tub. Seating at the table and the living room was a little tight but cozy. The fireplace was great for drying our gear since there is no washer and dryer. Beautiful views. The only two things I would suggest is leaving ice melt/salt for the stairs. They got icy after it rained and were quiet slippery. Also an extra drying rack would have been great...
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

NEW LISTING Dobie Slopeside Retreat: Trails+Tastings+Peace

10.0 out of 10, Exceptional, (14)
"Great place to stay! If you ski…you’re right there. If you don’t, you have a picturesque place to watch. All the amenities, nice and clean with really nice hosts. We enjoyed our stay and hope to come back."
NEW LISTING Dobie Slopeside Retreat: Trails+Tastings+Peace

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

9.8 out of 10, Exceptional, (173)
"Excellent stay overall. Weather kept us from enjoying the outside much but the cozy fireplace inside was super nice, especially with the supplied wood. Furniture was comfy and the smart TVs and streaming/cable was fabulous! "
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

9.4 out of 10, Exceptional, (83)
"Beautiful area and beautiful home."
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

10.0 out of 10, Exceptional, (49)
"We had a great family ski trip with the convenience of the cabin. After skiing it is nice to come back to a warm, comfy cabin that has nice kitchen, warm fireplaces and hot tub to relax. We would highly recommend! "
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

Wintergreen Resort Getaway w/ Deck, Mountain View!

8.8 out of 10, Excellent, (8)
"We really enjoyed our stay at this charming home! The house was immaculately clean, spacious, and so well-equipped—it truly felt like home away from home.The views from the back deck were amazing.We highly recommend this vacation home to anyone looking for a memorable time!"
Wintergreen Resort Getaway w/ Deck, Mountain View!

Squirrel Tree House

10.0 out of 10, Exceptional, (1)
"The house was beautiful and well stocked. The owner thought of everything and all the light switches were labeled which helped a lot. All of the appliances were top notch and the Keurig coffee maker had everything that was needed. Beds were very comfortable and each room had its own thermostat. Overall, excellent stay!"
The price is CA $312
CA $648 total
includes taxes & fees
Mar 18 - Mar 19
Squirrel Tree House

The Modern Mountain Condo

10.0 out of 10, Exceptional, (21)
"Comfortable stay for a father son ski trip. "
The price is CA $142
CA $317 total
includes taxes & fees
Mar 9 - Mar 10
The Modern Mountain Condo

Blue Ridge Mountain Retreat in Wintergreen

9.2 out of 10, Wonderful, (63)
"The house is large with lots of group area. The kitchen is very well stocked and perfect for a large group. Many bedrooms and beds everyone in our group was very comfortable. Many lights either did not work or had burnt out light bulbs we arrived at night, so this made things a little difficult. Please be aware that the house is up a very steep hill. We had freezing rain at night, which turned the driveway into a sheet of ice. We purchased ice melt and shoveled the driveway ourselves to be...
Blue Ridge Mountain Retreat in Wintergreen

Large and Luxurious Exec 5BR Chalet

10.0 out of 10, Exceptional, (245)
"Perfect location for family ski trip"
Large and Luxurious Exec 5BR Chalet

Wintergreen Resort Studio w/ Deck & Ski-Out Access

9.8 out of 10, Exceptional, (30)
"Awesome spot! Very clean, super close to the slopes like 1 minute walk."
Wintergreen Resort Studio w/ Deck & Ski-Out Access

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (267)
"The date of my stay was Sun Feb 9 - Tues Feb 11, 2025. It was a great place to stay with beautiful views. Our stay was short. We were there for my son to participate in WASI- Wintergreen Alpine Special Invitational. Travel to the Mountain Inn for ski competition and celebration was easy. I really enjoyed having the full kitchen so we could make breakfast each day. The washer and dryer were helpful for keeping ski bibs clean and dry."
The price is CA $151
CA $341 total
includes taxes & fees
Mar 18 - Mar 19
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (174)
"We have stayed here twice in the last two months. Both rooms were immaculately clean! Front office staff was pleasant and accommodating both times (It was the same woman both times...I just can't remember her name. ) If you are going to stay here, you so need to bring a hair dryer, conditioner (shampoo is provided), creamer( if you don't like French vanilla)"
The price is CA $149
CA $166 total
includes taxes & fees
Mar 16 - Mar 17
Valley Extended Suites

The Ultimate Escape. Unpack, Relax, Enjoy

10.0 out of 10, Exceptional, (11)
"Wife and I were looking for a place away from the hustle that comes with NOVA normally, and especially the weekend of the inauguration. I must say we found the absolute best spot. Nelson county has always been a favorite spot for us to go to, but most of the time we have made day trips. I absolutely love being able to post up for a weekend in a quiet setting and being able to relax. Even the pup enjoys the quiet and are keen to relax next to the stoves. Most places just leave it up to you to...
The Ultimate Escape. Unpack, Relax, Enjoy

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (40)
"Just as we had hoped and very comfortable beds "
The price is CA $287
CA $515 total
includes taxes & fees
Mar 18 - Mar 19
Ivy Rose Cottage nestled b/t Cville & Vineyards

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was very nicely set up, clean, and comfortable. The property manager was in constant contact with me to make sure I had everything I needed. I would highly recommend this place to anyone looking for a quiet relaxing escape. "
The price is CA $274
CA $395 total
includes taxes & fees
Mar 6 - Mar 7
Love Ridge Mountain Lodging
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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Other types of properties in Wintergreen you may be interested in

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (294)
"Perfect ski weekend rental. Great communication with Scott. Kitchen is nicely equipped. Hot tub is hot and was perfect for soaking and relaxing after a great day of skiing."
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!

10.0 out of 10, Exceptional, (233)
"Clean, well maintained, phenomenal views. Comfy beds, lots of blankets, and pillows. We will definitely book again!"
Best views on Mountain! Breathtaking 5 Star. Avail March 3-7 Break! BOOK NOW!

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (309)
"Clean, cozy,and convenient!"
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.

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?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: Visitors give good reviews to this Wintergreen vacation home rental, which is located on a lake and has an outdoor pool, a fireplace, 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. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation. Some other top choices in Wintergreen are Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub! and Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK.

How many vacation rentals are there in Wintergreen?

Choose from 44 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.