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Compare 280 Vacation Homes in Massies Mill with updated reviews, rates, and availability.

Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

9.8 out of 10, Exceptional, (62)
"Great location and awesome house. It was exactly what we wanted for a low key getaway with friends. "
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

Wintergreen Resort Home w/ 2 Decks + Ski Access!

9.2 out of 10, Wonderful, (38)
"The property location was great. In the heart of wintergreen with great views. The firplace on back deck was a great addition so we could enjoy evenings outside. My only complaint was the bed. It lists as queen and was not, and was also very "wore out" and in need of replacing. The bathrooms are a little tight and the toilet is low. If you are not a small person, it's a little cramped in there. The place wasn't dirty but could use a heavy dusting all over. Overall a nice little sopt on the...
Wintergreen Resort Home w/ 2 Decks + Ski Access!

Luxury Mountain House - Christmas Week still available

9.8 out of 10, Exceptional, (108)
"We booked this home to celebrate our anniversary and our nieces wedding. The Fall foliage was absolutely stunning, this property is so welcoming with gorgeous views and fully equipped with everything you could possibly need! The owners are such gracious hosts and their home is beautiful! We couldn’t have asked for a better location and we definitely will be back! Thanks for everything!!!"
Luxury Mountain House - Christmas Week still available

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

10.0 out of 10, Exceptional, (36)
"Pleasant stay!"
Modern Luxe Treetop Retreat w/Gas Fire Pit, Steps to Ski & Hike! 100% 5 Star!

Wintergreen Resort Getaway w/ Deck, Mountain View!

8.8 out of 10, Excellent, (5)
"We loved the place. Lots of room. The deck is awesome. "
Wintergreen Resort Getaway w/ Deck, Mountain View!

Updated! 5Br Home / Wineries / Breweries / Hiking

10.0 out of 10, Exceptional, (6)
"We enjoyed the house and how close it was to some of our favorite places, like Devils Backbone and Bold Rock. The basement was a lot of fun for the kids and adults! It was very clean and Ryan was easy to communicate with. We would definitely stay again!"
Updated! 5Br Home / Wineries / Breweries / Hiking

Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

10.0 out of 10, Exceptional, (56)
"Great place with great communication; perfect for a girls weekend in a beautiful area!"
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

9.6 out of 10, Exceptional, (16)
"This stay was perfect for our early Thanksgiving. Plenty of space and things to do without leaving the house. "
Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

Kick back at Virginia’s premier ski and golf resort

10.0 out of 10, Exceptional, (127)
"Second time here. Outstanding home with nothing missing. Nothing. Host is awesome. Came by herself to fix an issue, beyond what anyone else would do. Everything was wonderful. Plenty of supplies that others have you bring. This is a 6 star, better than any 5. Do yourself a favor and stay here."
Kick back at Virginia’s premier ski and golf resort

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

9.6 out of 10, Exceptional, (283)
"We came to stay in this area to attend my best friend's wedding. There were around 100 guests at the wedding and everyone had rented a home in the area. Our location was perfect! We were near other guests, the venue, and several breweries. There were several activities planed at the resort as well. We were able to spend one day in Charlottesville as well but it was around a 50 minute drive. We really enjoyed the view and trails around the home. There are several balconies to relax on but we...
The price is SAR 560
SAR 1,442 total
includes taxes & fees
4 Dec - 5 Dec
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Come and enjoy a beautiful view and relaxing time at Windy Knoll....

10.0 out of 10, Exceptional, (194)
"Windy Knoll is the best of all worlds - a quiet mountain retreat to relax at and disappear into nature, while being close enough to multiple great towns to enjoy what they have to offer as well. The owners clearly love this home, always upgrading to make the experience more enjoyable. Can't get enough of this place!"
Come and enjoy a beautiful view and relaxing time at Windy Knoll....

Unbeatable Views Atop Wintergreen 4min to Skiing

10.0 out of 10, Exceptional, (117)
"We loved the beautiful views and the warmth of the property. We prepared a few meals and found everything that we needed in the kitchen. The dens were large enough to seat us all together as a family and the property owners were quick to respond to any questions we had. "
Unbeatable Views Atop Wintergreen 4min to Skiing

Wintergreen Home w/ Hot Tub, Deck & Mountain Views

9.6 out of 10, Exceptional, (183)
"We had a fantastic day at this property! The house is great and easily includes enough room for two couples with two kids, so the two of us had plenty of room. We really enjoyed the hot tub and mountain views. We were really close to one of the ski slopes, so staying here if you are a skier would be ideal. And it was just a short 10 minute walk to the local market to get supplies. The owner reached out to make sure we had everything we needed. "
Wintergreen Home w/ Hot Tub, Deck & Mountain Views

Spacious + Serene Mtn Top Escape, 4 En Suites

10.0 out of 10, Exceptional, (28)
"Spent a week with an old friend visiting some vineyards and breweries. Went on a hot air balloon ride from Charlottesville, dined at the Farmhouse at Veritas and took a few hikes. Enjoyed it all. "
The price is SAR 637
SAR 1,783 total
includes taxes & fees
1 Dec - 2 Dec
Spacious + Serene Mtn Top Escape, 4 En Suites

Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort

9.8 out of 10, Exceptional, (121)
"Conveniently located on Wintergreen resort, minutes away from the convenience store and easy drive to all the main local points of interest. The house was clean and comfortable and the views outside were simply spectacular. house "
Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort

Blue's Barn: Nelson151 Escape + Mountain Views

9.4 out of 10, Exceptional, (8)
"We stayed for our wedding weekend, and it was perfect! Cute, comfy, cozy. The kitchen was well appointed and the furnishings were tops. We slept like a dream in the bed. 10/10 would recommend."
The price is SAR 1,146
SAR 1,816 total
includes taxes & fees
28 Nov - 29 Nov
Blue's Barn: Nelson151 Escape + Mountain Views

Beautiful 4-season Mountain Home- New Listing

10.0 out of 10, Exceptional, (18)
"This place is superclean, bright, and very comfortable. "
The price is SAR 748
SAR 1,986 total
includes taxes & fees
2 Dec - 3 Dec
Beautiful 4-season Mountain Home- New Listing

Heaven On Earth ~ Wintergreen Mountain

10.0 out of 10, Exceptional, (3)
"We love Wintergreen. We used to own a house up there so we know the area very well. This was our first time staying at this property and not only did it have the marvelous view from the top of the mountain that only devils knob loop has, but the house itself was everything we could've asked for and more. Very comfortable and very beautiful. We hope we will get to come back and stay here again. It is definitely our new favorite up on the mountain."
Heaven On Earth ~ Wintergreen Mountain

The Branch at Afton Mountain Retreat

10.0 out of 10, Exceptional, (23)
"Would recommend this lovely house for a weekend getaway or longer stay!"
The price is SAR 883
SAR 1,634 total
includes taxes & fees
2 Dec - 3 Dec
The Branch at Afton Mountain Retreat

Get out of the city and enjoy the country life at the Buffalo River Bungalow

9.8 out of 10, Exceptional, (39)
"The place is so pretty, well stocked kitchen including coffee and essentials for guests, clean, screened in porch, creek side, lovely sound of moving water, fire pit with everything needed for your enjoyment. Not far from many hiking trails and breweries. Great getaway!"
Get out of the city and enjoy the country life at the Buffalo River Bungalow
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 property types in Massies Mill

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 SAR 526
SAR 1,084 total
includes taxes & fees
30 Nov - 1 Dec
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

10.0 out of 10, Exceptional, (65)
"The cabin is super cute and close to breweries. We had a great time and the host is amazing! "
The price is SAR 488
SAR 746 total
includes taxes & fees
4 Dec - 5 Dec
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (51)
"This was our second time at this location. It is well equipped, clean, comfortable and the location is great. It sits at the top of the ridge, so views of sunrise and the evening sky are beautiful. The owners are responsive and accommodating. We "
Endless Mountain Top Views from All The Way Up!
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.