Massies Mill Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Massies Mill

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

9.0 out of 10, Wonderful, (285)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is HK$824
HK$1,904 total
includes taxes & fees
27 Jul - 28 Jul
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

9.6 out of 10, Exceptional, (40)
"We took our two kids and our poodle, Rocky, for a few days of hiking and unplugging! It was the perfect spot!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

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

10.0 out of 10, Exceptional, (27)
"It was a beautiful stay as described. "
The price is HK$1,138
HK$1,781 total
includes taxes & fees
24 Jul - 25 Jul
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

10.0 out of 10, Exceptional, (13)
"We loved staying at this property. Easily accommodated our family and was such a pretty setting. Host was excellent in answering questions and providing information. Would definitely stay here in the future."
Luxury Log Cabin Getaway: Near Wintergreen Resort & Shenandoah Valley

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

10.0 out of 10, Exceptional, (237)
"Absolutely loved my second stay at the gorgeous property! The sunrise and sunset views can’t be beat. "
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

10.0 out of 10, Exceptional, (39)
"Beautiful property and very responsive host. Nice place to stay. "
The price is HK$1,272
HK$2,318 total
includes taxes & fees
2 Aug - 3 Aug
Spy Run Hideaway is a 1/2 mile from the Blue Ridge Parkway & pet friendly!

Afton Mountain Vineyards

2.5 star property
The price is HK$2,649
HK$2,975 total
includes taxes & fees
27 Jul - 28 Jul
Afton Mountain Vineyards

Whimsical Creekside Cabin

10.0 out of 10, Exceptional, (26)
"Had a very quiet relaxing stay "
The price is HK$805
HK$1,743 total
includes taxes & fees
4 Aug - 5 Aug
Whimsical Creekside Cabin

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 HK$1,410
HK$2,055 total
includes taxes & fees
30 Jul - 31 Jul
Love Ridge Mountain Lodging

Family Friendly Log Cabin Nestled in Blue Ridge Foothills

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very well equipped and clean! The owner was super nice and responsive! Great stay!"
Family Friendly Log Cabin Nestled in Blue Ridge Foothills

Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking

10.0 out of 10, Exceptional, (12)
"The house was lovely. The location was great. Plenty of space for everyone. We really enjoyed this home."
Hot Tub EV Charger Pool Dog OK Grill Tennis Hiking

Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

9.8 out of 10, Exceptional, (48)
"Great place, easy to find, and quick drive to the Wontergreen Resort!"
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

Rustic Mountain Retreat-Bear Paw

9.8 out of 10, Exceptional, (229)
"Thanks for sharing your cabin with us! We loved the fireplace and had all the tools we needed for cozy meals."
Rustic Mountain Retreat-Bear Paw

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

9.6 out of 10, Exceptional, (128)
"This property is one of the best prperties we have ever stayed at. The owner is very responsive and goes the extra mile. We will definitely rent this property again!!"
The price is HK$863
HK$1,957 total
includes taxes & fees
28 Jul - 29 Jul
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

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

10.0 out of 10, Exceptional, (52)
"Really cool property on the Piney River. Great fly fishing in the back yard. Tons of outdoor space- house itself is beautiful. Kids enjoyed their spring break hanging outside and fishing. "
Charming cozy RIVERFRONT cottage on the Piney River. A little slice of heaven!

Updated, Cheerful Home Minutes to SVU, VMI and W&L

8.6 out of 10, Excellent, (27)
"The property was easy to navigate to and the neighborhood was very quiet. It had a nice big yard and the theatre room was fun!"
The price is HK$699
HK$1,675 total
includes taxes & fees
27 Jul - 28 Jul
Updated, Cheerful Home Minutes to SVU, VMI and W&L

Charming 2-bedroom condo in beautiful Wintergreen Resort

10.0 out of 10, Exceptional, (1)
"We stayed here for a couple of nights over July 4th and it was a nice short getaway. The condo is in a good location - 5 min walk to resort restaurants - and is very comfortable. The kitchen is well-equipped with plenty of cooking tools. The living room seating space was comfortable and allowed for just hanging out. We really enjoyed our stay! "
The price is HK$1,177
HK$3,006 total
includes taxes & fees
24 Jul - 25 Jul
Charming 2-bedroom condo in beautiful Wintergreen Resort

Wintergreen Resort Studio w/ Deck & Ski-Out Access

9.8 out of 10, Exceptional, (33)
"Awesome spot! Very clean, super close to the slopes like 1 minute walk."
Wintergreen Resort Studio w/ Deck & Ski-Out Access

Unwind at Bear Pause, located right at Wintergreen Resort.

10.0 out of 10, Exceptional, (1)
"There were a few little hiccups, the top bunk bar was not attached (not an issue as it wasn’t fully needed) and the oven was broken but I message the owner and he replied back very quickly. Neither were an issue for us. The house was perfect! Plenty of cooking supplies for our crew of 12. We loved the deck and spent plenty of time out there and there were more than enough towels for everyone. The check out rules were very clear and reasonable. I would say that something should be listed for the...
The price is HK$1,962
HK$4,258 total
includes taxes & fees
27 Jul - 28 Jul
Unwind at Bear Pause, located right at Wintergreen Resort.

Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

9.8 out of 10, Exceptional, (136)
"Beautiful property. Great placee to rest and relax."
Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Massies Mill Hotel Reviews

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?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: This holiday home rental outside of Massies Mill is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.