Holiday Rentals in Massies Mill

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Our top choices for Massies Mill holiday rentals

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 €404
includes taxes & fees
18 May - 19 May
Afton Mountain Vineyards

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, (55 reviews)
"Great property, peaceful setting, great owner response."
United States
Tim V.
The price is €398
includes taxes & fees
20 May - 21 May
RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.

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 €251
includes taxes & fees
18 May - 19 May
Peacefull, private Cabin! 140 acres,mile of river trails! 10 minutes to Rt.151!

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 €283
includes taxes & fees
18 May - 19 May
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Enjoy breweries, wineries, hikes & music · Short walk to the resort and 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 €270
includes taxes & fees
18 May - 19 May
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

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.
Stoneridge Woods 05 with Wintergreen Advantage

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.
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (17 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is €187
includes taxes & fees
18 May - 19 May
Love Ridge Mountain Lodging

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, (183 reviews)
"Everything was amazing "
United States
Richard
The price is €169
includes taxes & fees
18 May - 19 May
Cozy cabin for 2 w/ great mt views & walking trails!

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 €217
includes taxes & fees
19 May - 20 May
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

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, (128 reviews)
"Rooms a clean thermostats are easy to use and everything is easily accessible"
United States
JOSHUA KAMAU KARIUKI
The price is €223
includes taxes & fees
18 May - 19 May
Escape to the Blue Ridge Mountains at Wine-tergreen!

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great. "
United States
Nathan T.
The price is €132
includes taxes & fees
18 May - 19 May
Whole House

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.
Cozy Lux Condo at Wintergreen Resort

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 €234
includes taxes & fees
20 May - 21 May
Diamond Hill Studio 09 with Wintergreen Advantage

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 €230
includes taxes & fees
18 May - 19 May
Wintergreen Condo -Steps to Ski and restaurants

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)
"Everything was perfect! "
United States
Danielle B.
The price is €218
includes taxes & fees
19 May - 20 May
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is €523
includes taxes & fees
20 May - 21 May
Modern Nellysford Getaway on 40 Private Acres!

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.
The price is €232
includes taxes & fees
25 May - 26 May
Endless Mountain Top Views from All The Way Up!

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 €254
includes taxes & fees
18 May - 19 May
Panoramic Peak: Wintergreen Condo with Views

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 €500
includes taxes & fees
18 May - 19 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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Find out more about Massies Mill

Everything you need to know about Massies Mill holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Massies Mill holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Massies Mill holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Massies Mill holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Massies Mill. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Massies Mill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Massies Mill holiday rentals we have selected for you start as low as €128 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Massies Mill rentals

At Expedia, we put the best Massies Mill holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Massies Mill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Massies Mill holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Massies Mill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.