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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sep - 7 Sep
In two months
3 Oct - 5 Oct

Vacation Homes in Massies Mill

Upscale and Family-Friendly in Wintergreen
Indoor spa tub

Upscale and Family-Friendly in Wintergreen

9.8 out of 10, Exceptional, (23)
"We absolutely loved our stay. Great hiking access point and very family/pet friendly. Would love to come stay again!"
Upscale and Family-Friendly in Wintergreen
Mountaintop Wintergreen Resort Home w/ Deck, Views
Interior

Mountaintop Wintergreen Resort Home w/ Deck, Views

9.8 out of 10, Exceptional, (53)
"Second time staying here and we had the best time. Great for a weekend getaway to hang out with friends and family. "
Mountaintop Wintergreen Resort Home w/ Deck, Views
NEW! Secluded Farmhouse + Solar Heated Pool + Firepit
Exterior

NEW! Secluded Farmhouse + Solar Heated Pool + Firepit

10.0 out of 10, Exceptional, (25)
"We had a great time. Very pretty house in a very pretty setting!"
NEW! Secluded Farmhouse + Solar Heated Pool + Firepit
White Rock Cabin
Fridge, microwave, oven, stovetop

White Rock Cabin

10.0 out of 10, Exceptional, (208)
"Above and beyond on everything highly recommend staying here"
White Rock Cabin
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Property grounds

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

8.8 out of 10, Excellent, (28)
"The property was easy to navigate to and the neighborhood was very quiet. It had a nice big yard and the theatre room was fun!"
The price is AED 327
AED 788 total
includes taxes & fees
11 Aug - 12 Aug
Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Smart TV, fireplace, video games, DVD player

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

10.0 out of 10, Exceptional, (295)
"The house was perfect for us. Plenty of space for everyone to hang out together. "
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
80s glam house w/ hot tub, mtn views near W&L, VMI
Dining

80s glam house w/ hot tub, mtn views near W&L, VMI

2.0 star property
10.0 out of 10, Exceptional, (8)
"We had a great little break from the hustle and bustle of life. We are locals and it was nice to just get away for a few days"
The price is AED 601
AED 1,789 total
includes taxes & fees
11 Aug - 12 Aug
80s glam house w/ hot tub, mtn views near W&L, VMI
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Outdoor spa tub

Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

10.0 out of 10, Exceptional, (46)
"Check-in process was a breeze, communication with the hosts was super easy and consistent. Place was very clean and exactly as appears in the pictures. My group had an amazing time and loved the location of this property. Would 110% stay here again!"
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Cooler in the mountains, with hot tub.
Property grounds

Cooler in the mountains, with hot tub.

9.8 out of 10, Exceptional, (66)
"House was perfect for a weekend of skiing. You’re able to walk to the resort from the house which was a huge plus since it was a packed weekend. Overall great stay! "
Cooler in the mountains, with hot tub.
Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV
Terrace/patio

Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV

9.4 out of 10, Exceptional, (3)
"The property was well stocked and the location was excellent. There was plenty of firewood for the fireplace and the hot tub was perfect after a long day of skiing at the resort. "
Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
Fridge, microwave, oven, stovetop

Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

9.8 out of 10, Exceptional, (41)
"Beautiful property and very responsive host. Nice place to stay. "
The price is AED 595
AED 1,105 total
includes taxes & fees
11 Aug - 12 Aug
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
Property grounds

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

10.0 out of 10, Exceptional, (32)
"Loved the home! Was a perfect experience for us."
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
Thrilling Views HotTub Sauna Gym EV Charger DogOK
Interior

Thrilling Views HotTub Sauna Gym EV Charger DogOK

10.0 out of 10, Exceptional, (1)
"Beautiful place! Amazing views! Great hospitality! Has everything you need! Plenty of amenities. Host provided everything we needed. "
Thrilling Views HotTub Sauna Gym EV Charger DogOK
Modern Luxury Mountain Home within Wintergreen Retreat Collection
Smart TV, fireplace, video games, video library

Modern Luxury Mountain Home within Wintergreen Retreat Collection

9.8 out of 10, Exceptional, (50)
"Perfect place to relax and enjoy the company of friends and family. "
Modern Luxury Mountain Home within Wintergreen Retreat Collection
Unwind at Bear Pause, located right at Wintergreen Resort.
Outdoor dining

Unwind at Bear Pause, located right at Wintergreen Resort.

10.0 out of 10, Exceptional, (1)
"There were a few little hiccups, the top bunk bar was not attached (not an issue as it wasn’t fully needed) and the oven was broken but I message the owner and he replied back very quickly. Neither were an issue for us. The house was perfect! Plenty of cooking supplies for our crew of 12. We loved the deck and spent plenty of time out there and there were more than enough towels for everyone. The check out rules were very clear and reasonable. I would say that something should be listed for the...
The price is AED 1,102
AED 2,355 total
includes taxes & fees
2 Sep - 3 Sep
Unwind at Bear Pause, located right at Wintergreen Resort.
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, (134)
"Excellent house close to the slopes"
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Blue's Barn: Central to Wineries & Breweries
Pool

Blue's Barn: Central to Wineries & Breweries

9.4 out of 10, Exceptional, (12)
"Would recommend to anyone who wants a romantic getaway "
Blue's Barn: Central to Wineries & Breweries
Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!
Outdoor dining

Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!

9.2 out of 10, Wonderful, (49)
"There was so much to do, you don’t have to leave the place. However, it’s a great area to explore as well. "
Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!
Spacious + Serene Mtn Top Escape, 4 En Suites
Fridge, microwave, oven, stovetop

Spacious + Serene Mtn Top Escape, 4 En Suites

10.0 out of 10, Exceptional, (45)
"Property was very nice and great location."
The price is AED 643
AED 1,769 total
includes taxes & fees
11 Aug - 12 Aug
Spacious + Serene Mtn Top Escape, 4 En Suites
Rockfish River Retreat
Property grounds

Rockfish River Retreat

2.0 star property
10.0 out of 10, Exceptional, (11)
"Everything was perfect for us. Beautiful area!"
Rockfish River Retreat
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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Top Massies Mill Hotel Reviews

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

10/10 Excellent
"The condo was absolutely lovely! We had great time in Wintergreen and will definitely go back. "
Dawn C. 2-night trip
Posted 7 days ago
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!