Massies Mill Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Massies Mill

Our top choices for Massies Mill vacation rentals

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

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

10.0 out of 10, Exceptional, (60)
"Loved our stay - the house, location, and amenities were perfect for us!"
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Miscellaneous

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

10.0 out of 10, Exceptional, (243)
"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!
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Exterior

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

10.0 out of 10, Exceptional, (32)
"Great property and host"
The price is ￥21,403
￥33,485 total
includes taxes & fees
Sep 28 - Sep 29
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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
Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.
Fridge, microwave, oven, stovetop

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."
The price is ￥20,665
￥35,805 total
includes taxes & fees
Sep 28 - Sep 29
Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.
Wintergreen. Sunset Vista Villa - Sea of Mountains
Interior

Wintergreen. Sunset Vista Villa - Sea of Mountains

10.0 out of 10, Exceptional, (80)
"Everything was great!"
The price is ￥17,412
￥39,442 total
includes taxes & fees
Oct 1 - Oct 2
Wintergreen. Sunset Vista Villa - Sea of Mountains
Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area
Property grounds

Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area

10.0 out of 10, Exceptional, (15)
"Nice time exploring the area"
Relax in Natures Beauty: Private Log Cabin with Spacious Open Living Area
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

9.0 out of 10, Wonderful, (292)
"Beautiful location and million dollar views are so true. The condo was clean and comfortable. Will stay again and recommend to everybody. "
The price is ￥15,626
￥36,099 total
includes taxes & fees
Sep 29 - Sep 30
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Love Ridge Mountain Lodging
Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
The price is ￥31,590
￥44,405 total
includes taxes & fees
Sep 29 - Sep 30
Love Ridge Mountain Lodging
Aftonshire Cottage - Heart of Afton's Wine Region
Fridge, microwave, oven, stovetop

Aftonshire Cottage - Heart of Afton's Wine Region

9.8 out of 10, Exceptional, (10)
"Better than advertised. Kitchen has everything needed. Perfect for two couples. Comfy firm beds. Beautiful views- enjoyed watching the horses out back and the roaming deer. The brewery across the street has a fantastic scratch kitchen food truck - and great staff. Would love to book again in the near future. "
Aftonshire Cottage - Heart of Afton's Wine Region
Log Cabin, 27 Acre Modern Mountain Escape, Pool, Hot Tub and Fireplace
4 bedrooms, desk, iron/ironing board, free WiFi

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

10.0 out of 10, Exceptional, (19)
"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
3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes
Dining

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
Upscale and Family-Friendly in Wintergreen
Indoor spa tub

Upscale and Family-Friendly in Wintergreen

9.6 out of 10, Exceptional, (24)
"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
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (48)
"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
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Pool

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"
The price is ￥16,237
￥36,801 total
includes taxes & fees
Sep 28 - Sep 29
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
Smart TV, fireplace, DVD player

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

9.8 out of 10, Exceptional, (52)
"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
Lotus View Retreat in Yogaville, Chalet with WiFi and AC
Smart TV, DVD player, books, video library

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."
The price is ￥23,647
￥39,945 total
includes taxes & fees
Sep 26 - Sep 27
Lotus View Retreat in Yogaville, Chalet with WiFi and AC
Wow! What A View!
Exterior

Wow! What A View!

10.0 out of 10, Exceptional, (53)
"Property was gorgeous with amazing mountain views! Comfortable beds, beautiful kitchen and large living room for relaxing. Great location. Can’t wait to stay here again!"
Wow! What A View!
Whimsical Creekside Cabin
Property grounds

Whimsical Creekside Cabin

10.0 out of 10, Exceptional, (28)
"Had a very quiet relaxing stay "
The price is ￥7,041
￥23,436 total
includes taxes & fees
Sep 28 - Sep 29
Whimsical Creekside Cabin
The Modern Mountain Condo
Property grounds

The Modern Mountain Condo

10.0 out of 10, Exceptional, (28)
"Ideal location for skiing at Wintergreen. "
The price is ￥14,900
￥35,117 total
includes taxes & fees
Oct 5 - Oct 6
The Modern Mountain Condo
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

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

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

10/10 Excellent
"We are so grateful we found this property. We were goi g to pay over 1000 for two rooms at the hotel down the road for two nights. Thankfully my sister found this as an alternative. It was so quaint and clean. It smelled good and everything looked brand new it was so well cared for. I could go on and on about the shower and how great the water pressure was. We were there two days and I took 3 showers because it was so nice. My parents and husband met the owner while I was gone early tog et ready for a wedding down the road and said they were very king. 10/10 would recommend and would stay again if we were ever in the area. "
Anna W. 2-night trip
Posted 3 days ago
Murphy’s Place 2-bedroom apartment near hiking skiing wineries and breweries.

Find out more about Massies Mill

Find out more about Massies Mill

Search for holiday rentals in Massies Mill on Expedia! You can easily find your home rentals, villas, holiday apartments in Massies Mill using one of the methods below:

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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?

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.