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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, (285)
"We really enjoyed our stay Host Scott was very informative and has very clear information. The house is very family friendly. We loved being able to use the fireplace. The hot tub was spectacular my wife usually never likes Hot Tubs but used this one twice. Kids loved the indoor basketball hoops and pac-man . My wife grew up with pac-man so she really loved it. We booked the house for my BD and we had some great memories. We were very lucky ski resort was open so the kids loved that. Thank so...
The price is CA $215
CA $553 total
includes taxes & fees
Jan 13 - Jan 14, 2025
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, (298)
"This house was so beautiful! It was the best stocked vrbo we've stayed in with everything for the kitchen, bath, games and even a few dog toys! The hosts have thought of every little detail. Highly recommend. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Best views on Mountain! Breathtaking 5 Star. Available Dec 13-15! Ski! BOOK NOW!

10.0 out of 10, Exceptional, (227)
"We cannot wait to book this property again for a longer stay! It is such a beautiful condo, so tastefully decorated, with the most spectacular views of sunrise and mountain ranges! Really a very special place to be! "
Best views on Mountain! Breathtaking 5 Star. Available Dec 13-15! Ski! BOOK NOW!

Walk to Mtn Inn & The Market

9.6 out of 10, Exceptional, (27)
"I grew up near Wintergreen but never spent any time in the area. Condo was exactly as advertised. Quiet neighbors."
Walk to Mtn Inn & The Market

Ski-In/Ski-Out Comfy Condo

10.0 out of 10, Exceptional, (19)
"Unit was very clean. Kitchen was well stocked. Neighbor upstairs was very noisy. Bed was not very comfortable. Otherwise nice and cozy. "
Ski-In/Ski-Out Comfy Condo

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

9.8 out of 10, Exceptional, (171)
"Amazing views along the blue ridge trail in wintergreen. Host was communicative and check in was easy! Plentry of room for our stay and guests. We thouroughly enjoyed our stay!"
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

Pine Cottage: Hot Tub and Central to Nelson 151

10.0 out of 10, Exceptional, (16)
"The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. "
The price is CA $311
CA $691 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Pine Cottage: Hot Tub and Central to Nelson 151

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

9.8 out of 10, Exceptional, (17)
"Was great! Ty"
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

Large Home With Spectacular Mountain Views Located In Wintergreen!

10.0 out of 10, Exceptional, (17)
"The area is beautiful and our crew really enjoyed their stay at your rental. It was very spacious, clean, and in a great location. The host was friendly and prompt with communications. We would definitely love to come back."
Large Home With Spectacular Mountain Views Located In Wintergreen!

Luxury Chalet, Best Views in Virginia

9.8 out of 10, Exceptional, (26)
"We particularly enjoyed the spectacular views. Beds were comfy. Found the decor a bit overdone. Lighting was hard to figure out (especially since we were directed to keep outside lighting at a minimum.) Master toilet didn't work (sent message to property manager). One bedroom on mid-level did not have a bathroom access (found that to be a little strange) and not represented in information about the house. Hot water not working in one of the kitchen sinks and took forever to get hot in the other...
Luxury Chalet, Best Views in Virginia

Blue Ridge Mountain Retreat in Wintergreen

9.2 out of 10, Wonderful, (62)
"We had an amazing time staying at Wintergreen. Ashley was super easy to work with and the home was very accommodating! Everything was clean, spacious, with everything we needed. There was plenty of fire wood. We look forward to returning! "
Blue Ridge Mountain Retreat in Wintergreen

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

10.0 out of 10, Exceptional, (121)
"Property was as advertised and there are no complaints. It was a bit small for the 6 adults ( 3 couples). The loft was nice but very warm when sleeping. The den seating was for crowded for us but the fireplace was appreciated on the very cold nights and morning. "
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

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

9.0 out of 10, Wonderful, (256)
"My wife Teresa and I have been staying here for 11 years now. Every year for the last eleven years we have stayed the last week of Oct. The view is incredible. It never gets old. Something else that is very important to my wife and I is that the foyer door is only about 15 feet from the parking lot and its a flat walkway. Also, once in the foyer, its literally 2 steps to the stairs which are only 9 stairs. Most condos at Wintergreen are a hike just getting to the front door of the unit. Not...
The price is CA $151
CA $350 total
includes taxes & fees
Jan 13 - Jan 14, 2025
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging

10.0 out of 10, Exceptional, (193)
"Everything about the property was planned and built with top quality. It was easy to communicate with Terry who was very friendly. We have never stayed at a property with such access to privacy yet many on-site activities. We loved it. Well worth the drive!"
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging

Cozy Country small two bedroom home.

9.6 out of 10, Exceptional, (13)
"This was a nice cozy comfortable house nearby Crabtree falls hiking! We would stay here again."
The price is CA $194
CA $351 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Country small two bedroom home.

5 Bedroom Hilltop Villa with Hot Tub and Magnificent Views

10.0 out of 10, Exceptional, (22)
"This home is very clean with plenty of room for a big family. Beautiful views! Fresh flowers and a basket of fruit welcomed us. "
5 Bedroom Hilltop Villa with Hot Tub and Magnificent Views

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (35)
"Nice quaint cottage. Exactly as described. Quick and friendly communication. "
The price is CA $286
CA $517 total
includes taxes & fees
Jan 13 - Jan 14, 2025
Ivy Rose Cottage nestled b/t Cville & Vineyards

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

10.0 out of 10, Exceptional, (66)
"The cabin is super cute and close to breweries. We had a great time and the host is amazing! "
The price is CA $187
CA $282 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

9.8 out of 10, Exceptional, (68)
"We had a wonderful time at this home. Everything was accurate in its description. The driveway is extremely steep so I would be suspect in the winter of how to get up, but we had no problem this time of year."
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

View from the Top

10.0 out of 10, Exceptional, (47)
"We really enjoyed our stay and the wonderful mountain vews! Very comfortable condo."
View from the Top
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, (285)
"We really enjoyed our stay Host Scott was very informative and has very clear information. The house is very family friendly. We loved being able to use the fireplace. The hot tub was spectacular my wife usually never likes Hot Tubs but used this one twice. Kids loved the indoor basketball hoops and pac-man . My wife grew up with pac-man so she really loved it. We booked the house for my BD and we had some great memories. We were very lucky ski resort was open so the kids loved that. Thank so...
The price is CA $215
CA $553 total
includes taxes & fees
Jan 13 - Jan 14, 2025
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Best views on Mountain! Breathtaking 5 Star. Available Dec 13-15! Ski! BOOK NOW!

10.0 out of 10, Exceptional, (227)
"We cannot wait to book this property again for a longer stay! It is such a beautiful condo, so tastefully decorated, with the most spectacular views of sunrise and mountain ranges! Really a very special place to be! "
Best views on Mountain! Breathtaking 5 Star. Available Dec 13-15! Ski! BOOK NOW!

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

10.0 out of 10, Exceptional, (298)
"This house was so beautiful! It was the best stocked vrbo we've stayed in with everything for the kitchen, bath, games and even a few dog toys! The hosts have thought of every little detail. Highly recommend. "
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 spa tub so you can immerse yourself in your vacation. Our travelers also rate Fantastic Mountain & Valley Views! 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 42 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.