Massies Mill Vacation Rentals

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Dec 8 - Dec 9
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Dec 9 - Dec 10
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Vacation Rentals in Massies Mill

Miscellaneous
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Wintergreen
10.0 out of 10, Exceptional, (252)
"Stayed 3 nights for a wedding at Wintergreen. Wonderful place with spectacular views "
United States
Michael S.
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!
Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio
Love Ridge Mountain Lodging

Love Ridge Mountain Lodging

3.0 star property
Montebello
10.0 out of 10, Exceptional, (13)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is ￥27,902
￥40,655 total
includes taxes & fees
Dec 9 - Dec 10
Love Ridge Mountain Lodging
Terrace/patio
New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Chestnut Springs
10.0 out of 10, Exceptional, (4)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
The price is ￥81,548
￥158,387 total
includes taxes & fees
Jan 7 - Jan 8, 2026
New Build! Log Cabin with Hot Tub in Wintergreen
Property grounds
Whimsical Creekside Cabin

Whimsical Creekside Cabin

Vesuvius
9.8 out of 10, Exceptional, (39)
"Had a very quiet relaxing stay "
United States
Joyce I.
The price is ￥11,883
￥29,821 total
includes taxes & fees
Dec 9 - Dec 10
Whimsical Creekside Cabin
Exterior
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Montebello
10.0 out of 10, Exceptional, (44)
"Nice quiet set of new cabins. Solid set of amenities. Really enjoyed our stay."
United States
Jesse C.
The price is ￥22,523
￥35,760 total
includes taxes & fees
Dec 10 - Dec 11
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Exterior
Wow! What A View!

Wow! What A View!

Wintergreen Resort
10.0 out of 10, Exceptional, (54)
"Very clean, very comfortable, easy to access - we honestly didn't want to leave."
United States
Josh W.
Wow! What A View!
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

Roseland
9.0 out of 10, Wonderful, (302)
"Great view!!"
United States
Suzanne W.
The price is ￥13,840
￥34,732 total
includes taxes & fees
Dec 9 - Dec 10
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Outdoor dining
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Wintergreen Resort
9.8 out of 10, Exceptional, (8)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
Fridge, microwave, oven, stovetop
2min to Ski Hot Tub EV Charger Mountain View DogOK

2min to Ski Hot Tub EV Charger Mountain View DogOK

Wintergreen Resort
10.0 out of 10, Exceptional, (17)
"Had a wonderful weekend stay! Close to the slopes and great location!"
United States
WR Q.
2min to Ski Hot Tub EV Charger Mountain View DogOK
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

Roseland
10.0 out of 10, Exceptional, (336)
"Great stay, highly recommended"
United States
Jeffrey E.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Property grounds
Large and Luxurious Exec 5BR Chalet

Large and Luxurious Exec 5BR Chalet

Pedlars Edge
10.0 out of 10, Exceptional, (250)
"Perfect location for family ski trip"
United States
Angie S.
Large and Luxurious Exec 5BR Chalet
Pool
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Roseland
9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
The price is ￥17,086
￥38,899 total
includes taxes & fees
Dec 9 - Dec 10
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Fridge, microwave, oven, stovetop
Hiker’s paradise! Come relax this summer!!!

Hiker’s paradise! Come relax this summer!!!

Roseland
10.0 out of 10, Exceptional, (36)
"Best place we have stayed around wintergreen hands down."
United States
Allen M.
Hiker’s paradise! Come relax this summer!!!
Smart TV, fireplace, video games, books
The newest and largest edition to the Wintergreen Retreat portfolio!

The newest and largest edition to the Wintergreen Retreat portfolio!

Wintergreen Resort
9.8 out of 10, Exceptional, (47)
"Beautiful property, well maintained. Perfect for a large group."
United States
Kenneth H.
The newest and largest edition to the Wintergreen Retreat portfolio!
Interior
Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen Resort
10.0 out of 10, Exceptional, (91)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
United States
Amanda W.
The price is ￥18,174
￥41,341 total
includes taxes & fees
Dec 9 - Dec 10
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Fridge, microwave, oven, stovetop
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

Roseland
10.0 out of 10, Exceptional, (68)
"Stunning scenic getaway! Perfect setting, beautiful decor, high end amenities, gracious host, serene outdoor spaces. One of best places we’ve stayed. Highly recommend."
United States
Diane L.
The price is ￥31,066
￥68,532 total
includes taxes & fees
Dec 11 - Dec 12
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!
Property grounds
Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.

Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.

Wintergreen Resort
9.8 out of 10, Exceptional, (53)
"Great place to stay in Wintergreen!"
United States
Caroline w.
Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.
Smart TV, fireplace, video games, DVD player
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

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

Wintergreen Resort
10.0 out of 10, Exceptional, (302)
"The home was very clean and beautiful. There were many great views in the mountains. Nathan and Kelly were very helpful with setting up tee times and getting pool passes. The resort has a few restaurants that were close and delicious. Wasn't chilly enough to use the fireplace but it did look inviting."
United States
Jack M.
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Outdoor dining
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

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

Wintergreen Resort
9.6 out of 10, Exceptional, (29)
"Great place to stay, would book again!"
United States
Jessica P.
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Interior detail
Afton Mountain Vineyards

Afton Mountain Vineyards

2.5 star property
Afton
10.0 out of 10, Exceptional, (1)
"Amazing little cottage with everything you need. Loved the back porch and listening to music from the winery and enjoying the view. Good news, did not hear the music inside. "
United States
Kristin
The price is ￥54,366
￥61,054 total
includes taxes & fees
Dec 9 - Dec 10
Afton Mountain Vineyards
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 condo!. Booking NOW for 2026!

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

10/10 Excellent
"The host was exceptionally friendly, informative and helpful. I had questions for the host before booking. She answered our questions quickly and was always gracious. When we asked if there was a mixer and specific baking dish, she said that she would order one for us. That was above and beyond our expectations. The condo is lovely, was clean and ready for guests. The furnishings are stylish, clean and comfortable. The beds were comfortable as well. The view!!! We took so many pictures of the beautiful view from the condo. That expansive view inspired us to go hiking. We found two great hiking trails close to the condo. When we got back from the hike, we used the unlimited firewood to have a wonderful fire in the fireplace. We played games and enjoyed watching something together on the tv over the fireplace. On Thanksgiving, we used the kitchen to make a wonderful meal and we dined at the dining table enjoying the view. There is a small market on the mountain if you need any last minute groceries. I encourage you to stay at this condo. Our family had a great time at this condo. Maureen is a wonderful host."
Mary G. 2-night trip
Posted 4 days ago
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

Find out more about Massies Mill

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Frequently asked questions

Are there vacation rentals in Massies Mill?

Yes, we have vacation rentals near popular local attractions in Massies Mill, or you can choose a secluded option if you're looking for relaxation.

What's the top vacation rental that Massies Mill has to offer?

Large and Luxurious Exec 5BR Chalet: This vacation home rental near Massies Mill is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Massies Mill?

While you're exploring the area, Crabtree Falls and Sherando Lake Recreation Area are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Lovingston Winery and Bold Rock Hard Cider Nellysford Cidery.

What are vacation rentals like in Massies Mill?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Massies Mill. Vacation rentals feature extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family trips or small group gatherings.