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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!
Exterior

Mountain Chalet – Panoramic Views of Blue Ridge Mountains!

9.8 out of 10, Exceptional, (62)
"Very comfortable well appointed house in an excellent location. The proximity of the AT and hikes we could walk to was greatly appreciated. The deck was wonderful…we utilized the gas fire pit every night. The trees blocked our view of mountains but we enjoyed listening to music and watching the squirrels. "
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
Wintergreen Resort Home w/ 2 Decks + Ski Access!
Roseland Vacation Rental | 3BR | 2BA | 1,875 Sq Ft | Stairs Required for Entry

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
Outside picture of house (Spring Time)

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!
Light-drenched living room with modern furnishings

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!
Roseland Vacation Rental | 4BR | 4BA | 1,500 Sq Ft | Stairs Required

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
The neighborhood is full of walking, hiking, and biking trails around lakes with beautiful mountain views.

Updated! 5Br Home / Wineries / Breweries / Hiking

10.0 out of 10, Exceptional, (6)
"All 11 of us agreed that this is our favorite house we've rented near Wintergreen ever! Perfect for 4 adults and 7 kids (ages 10-17) and very conveniently located to breweries and Wintergreen. We are already trying to figure out what dates we want to book for next year!"
Updated! 5Br Home / Wineries / Breweries / Hiking
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
Living area

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
Exterior

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

9.6 out of 10, Exceptional, (16)
"Beautiful, spacious house away from the main village. Nice furniture and very comfy beds! Nice gas fireplace that warms the great room up quickly. Nice leaf off views to the east. We had a great stay with wonderful fall leaf colors and great hiking in the area. As an owner/manager of resort property I would have given this house 5 stars except for some maintenance issues. A nonfunctioning icemaker in the fridge, a Brita filter in the fridge that had an old nonfunctioning filter, piles of leaves...
Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard
Kick back at Virginia’s premier ski and golf resort

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.
Fresh Private Hot Tub Lower Deck Relaxing Location in woods with Beautiful Views

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 AED 547
AED 1,411 total
includes taxes & fees
1 Dec - 2 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....
Our Windy Knoll - come and enjoy!

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
Terrace/patio

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
Wintergreen Vacation Rental | 3BR | 2BA | 1,300 Sq Ft | 2 Stories

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
Main living floor contains dining, kitchen, living room, and half bath.

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 AED 628
AED 1,749 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
Winter views on the patio, from the living room and kitchen.

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
Terrace/patio

Blue's Barn: Nelson151 Escape + Mountain Views

9.4 out of 10, Exceptional, (8)
"Would recommend to anyone who wants a romantic getaway "
The price is AED 1,021
AED 1,650 total
includes taxes & fees
27 Nov - 28 Nov
Blue's Barn: Nelson151 Escape + Mountain Views
Beautiful 4-season Mountain Home- New Listing
Living area

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 AED 731
AED 1,942 total
includes taxes & fees
2 Dec - 3 Dec
Beautiful 4-season Mountain Home- New Listing
Heaven On Earth ~ Wintergreen Mountain

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
Exterior

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 AED 863
AED 1,612 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
Exterior

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.
Entrance to High Ridge

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 AED 514
AED 1,060 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
Cabin sits on host's 34-acre mountain property. Private guest driveway/parking.

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 AED 477
AED 734 total
includes taxes & fees
27 Nov - 28 Nov
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Endless Mountain Top Views from All The Way Up!
Enjoy the stunning views from the balcony!

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.