Massies Mill Vacation Rentals

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Vacation Rentals in Massies Mill

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

10.0 out of 10, Exceptional, (244)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

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

10.0 out of 10, Exceptional, (327)
"The property is nestled very nicely on the mountain and convenient to the main lodge, restaurants and other attractions. We really enjoyed our stay. The condo was plenty big for the two of us and our dog. It is well-appointed Kudos to the owner, Heather, for thinking of everything to make our stay great. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

9.0 out of 10, Wonderful, (293)
"Beautiful location and million dollar views are so true. The condo was clean and comfortable. Will stay again and recommend to everybody. "
$216 nightly
The price is $243
Oct 2 - Oct 3
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (62)
"Loved our stay - the house, location, and amenities were perfect for us!"
$635 nightly
The price is $713
Oct 27 - Oct 28
Total with taxes and fees
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table

10.0 out of 10, Exceptional, (15)
"Nice time exploring the area"
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table

The Modern Mountain Condo

10.0 out of 10, Exceptional, (28)
"Ideal location for skiing at Wintergreen. "
$216 nightly
The price is $243
Oct 2 - Oct 3
Total with taxes and fees
The Modern Mountain Condo

Log Cabin, 27 Acre Modern Mountain Escape, Pool, Hot Tub and Fireplace

9.8 out of 10, Exceptional, (20)
"Thank you, we enjoyed our little vacation! The pool was the best part !"
Log Cabin, 27 Acre Modern Mountain Escape, Pool, Hot Tub and Fireplace

Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

9.6 out of 10, Exceptional, (49)
"We had the best weekend! Loved Lake Monocan and Devil’s Knob Spa. Also visited Three Notched and Devil’s Backbone. Condo worked very well. Beds were so comfortable and we lived kicking back on the patio. Will definitely rent again since it’s so close. Thanks for great communications!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

9.8 out of 10, Exceptional, (53)
"This was our second stay in Wintergreen. First time at this property. The condo was beautifully decorated, had all the necessities and the view was breathtaking. "
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

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

10.0 out of 10, Exceptional, (34)
"Great property and host"
$202 nightly
The price is $227
Oct 2 - Oct 3
Total with taxes and fees
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
$283 nightly
The price is $311
Oct 7 - Oct 8
Total with taxes and fees
Love Ridge Mountain Lodging

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

9.6 out of 10, Exceptional, (136)
"Very clean place and very accommodating host"
$239 nightly
The price is $268
Oct 2 - Oct 3
Total with taxes and fees
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Escape to the Blue Ridge Mountains at Wine-tergreen!

9.8 out of 10, Exceptional, (119)
"Well appointed and clean unit. Beds were comfortable and the kitchen had everything we needed. The balcony is a great place to have coffee and enjoy nature. "
$218 nightly
The price is $245
Oct 5 - Oct 6
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!

Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.

10.0 out of 10, Exceptional, (119)
"This is the perfect location, very clean, fabulous hosts, and nice, quiet neighborhood."
$216 nightly
The price is $243
Oct 5 - Oct 6
Total with taxes and fees
Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.

Lotus View Retreat in Yogaville, Chalet with WiFi and AC

10.0 out of 10, Exceptional, (4)
"The view really is that beautiful! It's rural and peaceful! The check-in and check-out was easy and the owners pleasant to work with. The house is very comfortable and open."
$250 nightly
The price is $269
Oct 6 - Oct 7
Total with taxes and fees
Lotus View Retreat in Yogaville, Chalet with WiFi and AC

3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

10.0 out of 10, Exceptional, (62)
"House was very nice. Great set up for family."
3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

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

8.0 out of 10, Very Good, (1)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Family Friendly Log Cabin Nestled in Blue Ridge Foothills

2.0 star property
10.0 out of 10, Exceptional, (13)
"Perfect beautiful cabin for a weekend getaway. Everything was clean and the kitchen well-stocked. Little thoughtful touches made you feel taken care of!"
Family Friendly Log Cabin Nestled in Blue Ridge Foothills

New Build! Log Cabin with Hot Tub in Wintergreen

10.0 out of 10, Exceptional, (2)
"Well appointed kitchen, beautiful cabin!"
$1,136 nightly
The price is $1,275
Oct 9 - Oct 10
Total with taxes and fees
New Build! Log Cabin with Hot Tub in Wintergreen

Deer Run - Mountain Getaway

10.0 out of 10, Exceptional, (231)
"We’ve been vacationing here yearly since 2018, it’s like coming home, we absolutely love Deer Run!"
Deer Run - Mountain Getaway
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

Find out more about Massies Mill

Find out more about Massies Mill

Everything you need to know about Massies Mill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Massies Mill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Massies Mill vacation 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 low season months. For more hustle and bustle, you may prefer to visit Massies Mill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $227 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Massies Mill rentals

At Expedia, we put the best Massies Mill vacation 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 vacation.

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 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?

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!: This vacation home rental near Massies Mill is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 Oak Ridge Estate.

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.