Massies Mill Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Massies Mill holiday rentals

Interior detail

Afton Mountain Vineyards

Afton Mountain Vineyards
2.5 star property
Afton
10.0 out of 10, Exceptional, (2 reviews)
"Cozy and comfortable with pond and mountain views. Wine tasting on site and easy access to Wintergreen. We loved our stay and will be back again!"
United States
Jennifer
The price is HK$3,277
HK$3,680 total
includes taxes & fees
19 May - 20 May
Afton Mountain Vineyards
Smart TV

RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.

RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.
Faber
10.0 out of 10, Exceptional, (54 reviews)
"Great property, peaceful setting, great owner response."
United States
Tim V.
The price is HK$2,819
HK$3,570 total
includes taxes & fees
20 May - 21 May
RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.
Terrace/patio

Peacefull, private Cabin! 140 acres,mile of river trails! 10 minutes to Rt.151!

Peacefull, private Cabin! 140 acres,mile of river trails! 10 minutes to Rt.151!
Faber
10.0 out of 10, Exceptional, (56 reviews)
"The entire home was very clean and comfortable. The property is stunning and worth exploring. "
United States
Mario
The price is HK$1,793
HK$2,251 total
includes taxes & fees
26 May - 27 May
Peacefull, private Cabin! 140 acres,mile of river trails! 10 minutes to Rt.151!
Exterior

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (111 reviews)
"Great and comfortable place to stay! Host was very welcoming and responsive. "
United States
Jon L.
The price is HK$1,304
HK$2,554 total
includes taxes & fees
18 May - 19 May
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Fridge, microwave, oven, stovetop

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is HK$810
HK$2,414 total
includes taxes & fees
16 May - 17 May
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Exterior

Stoneridge Woods 05 with Wintergreen Advantage

Stoneridge Woods 05 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"Loved the house. The layout was great and worked great for our family."
United States
Torry M.
The price is HK$1,636
HK$2,935 total
includes taxes & fees
16 May - 17 May
Stoneridge Woods 05 with Wintergreen Advantage
Snow and ski sports

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (38 reviews)
"Amazing spot! Ski in - out was so convenient and a quick walk to the village! Phyllis was amazing and the condo was beautiful! Would definitely book this condo again! "
United States
Susan J.
The price is HK$1,189
HK$3,131 total
includes taxes & fees
21 May - 22 May
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (16 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is HK$1,049
HK$1,647 total
includes taxes & fees
20 May - 21 May
Love Ridge Mountain Lodging
Property grounds

Cozy cabin for 2 w/ great mt views & walking trails!

Cozy cabin for 2 w/ great mt views & walking trails!
Schuyler
10.0 out of 10, Exceptional, (182 reviews)
"Everything was amazing "
United States
Richard
The price is HK$1,078
HK$1,475 total
includes taxes & fees
17 May - 18 May
Cozy cabin for 2 w/ great mt views & walking trails!
Property grounds

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, (153 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is HK$861
HK$1,943 total
includes taxes & fees
19 May - 20 May
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Outdoor dining

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (127 reviews)
"great stay"
United States
Vickie G.
The price is HK$909
HK$2,023 total
includes taxes & fees
21 May - 22 May
Escape to the Blue Ridge Mountains at Wine-tergreen!
Fridge, microwave, oven, stovetop

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great. "
United States
Nathan T.
The price is HK$705
HK$1,166 total
includes taxes & fees
19 May - 20 May
Whole House
Terrace/patio

Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed it so much! So cozy and close to the resort! "
United States
Katie B.
The price is HK$1,057
HK$2,361 total
includes taxes & fees
17 May - 18 May
Cozy Lux Condo at Wintergreen Resort
Exterior

Diamond Hill Studio 09 with Wintergreen Advantage

Diamond Hill Studio 09 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"Great location and cozy condo! "
United States
Molly M.
The price is HK$1,245
HK$2,091 total
includes taxes & fees
16 May - 17 May
Diamond Hill Studio 09 with Wintergreen Advantage
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (36 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is HK$892
HK$2,084 total
includes taxes & fees
19 May - 20 May
Wintergreen Condo -Steps to Ski and restaurants
Interior

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is HK$939
HK$1,899 total
includes taxes & fees
9 Jun - 10 Jun
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is HK$1,918
HK$4,763 total
includes taxes & fees
20 May - 21 May
Modern Nellysford Getaway on 40 Private Acres!
Property grounds

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (103 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
Endless Mountain Top Views from All The Way Up!
1 bedroom, desk, Internet, bed sheets

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (44 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
The price is HK$1,088
HK$2,277 total
includes taxes & fees
18 May - 19 May
Panoramic Peak: Wintergreen Condo with Views
Smart TV, fireplace, ping pong, books

4 BR cabin mins to trails & breweries pets welcome

4 BR cabin mins to trails & breweries pets welcome
Chestnut Springs
9.6 out of 10, Exceptional, (34 reviews)
"Beautiful place. Exactly as depicted in the listing. Very responsive host with questions prior to my stay."
United States
Philip S.
The price is HK$1,515
HK$4,577 total
includes taxes & fees
17 May - 18 May
4 BR cabin mins to trails & breweries pets welcome
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

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!

10/10 Excellent
"Beautiful house right on the river. We had an amazing time just sitting outside listening to the sound of the water rolling by. Inside, the house is impeccable with everything you need to spend some relaxing time away. Our dogs were quite happy as well and were lounging by the river and exploring the property all day long. We will be back again. Thank you Maria!"
Mark V. 3-night trip
Posted 15 hours ago
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

Find out more about Massies Mill

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Frequently asked questions

Are there holiday rentals in Massies Mill?

Yes, there are holiday rentals close to the most popular sights in Massies Mill, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Massies Mill has to offer?

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI: This holiday home rental outside of Massies Mill is located in the mountains, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind.

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 wider area, you’ll find Lovingston Winery and Oak Ridge Estate.

What are holiday rentals like in Massies Mill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Massies Mill. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips.