Default HTG hotel image

Massies Mill Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Massies Mill vacation rentals

Ravens Roost, 3 Bedrooms, Hot Tub, Mountain View | Terrace/patio

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (21 reviews)
"Very quiet and peaceful stay. "
United States
Timika
The price is ￥22,741
￥35,289 total
includes taxes & fees
Jul 28 - Jul 29
Love Ridge Mountain Lodging
Outdoor dining

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (17 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is ￥22,033
￥48,571 total
includes taxes & fees
Jul 23 - Jul 24
Historic Bungalow 30 minutes from Wintergreen
Beach towels

Cozy Country small two bedroom home.

Cozy Country small two bedroom home.
Roseland
9.8 out of 10, Exceptional, (19 reviews)
"Lovely cozy place in the mountains, we had a total blast!"
United States
Prabir
The price is ￥22,033
￥40,324 total
includes taxes & fees
Jul 27 - Jul 28
Cozy Country small two bedroom home.
Exterior

Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is ￥24,971
￥28,043 total
includes taxes & fees
Jul 23 - Jul 24
Branch and Barrel
Smart TV, DVD player, books, music library

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (109 reviews)
"Beautiful cabin!"
United States
Anna W.
The price is ￥21,126
￥31,938 total
includes taxes & fees
Aug 18 - Aug 19
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (58 reviews)
"Wonderful location. Wonderful host. We will be back!"
United States
April S.
The price is ￥12,850
￥35,326 total
includes taxes & fees
Aug 5 - Aug 6
Where the Trail Ends
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, (112 reviews)
"Nice place!"
United States
Gregory G.
The price is ￥19,745
￥48,272 total
includes taxes & fees
Jul 27 - Jul 28
Endless Mountain Top Views from All The Way Up!
Interior

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (39 reviews)
"House was perfect for overnight stay. 30 min from Vines Center and easy to find."
United States
Unspecified U.
The price is ￥14,626
￥24,199 total
includes taxes & fees
Jul 23 - Jul 24
Whole House
Exterior

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (10 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
The price is ￥18,201
￥51,022 total
includes taxes & fees
Jul 23 - Jul 24
Laurelwood Hollow: Walk to Ski & Swim
Exterior

New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail

New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
Montebello
9.6 out of 10, Exceptional, (12 reviews)
"The property was very clean and located on scenic property. The owner provided many extra perks such as firewood, fire pit, grill, cooking materials, and several toiletries! Would definitely recommend this location to anyone!"
United States
Donna
The price is ￥21,299
￥34,369 total
includes taxes & fees
Jul 23 - Jul 24
New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
Coffee/tea maker, fridge, microwave, oven

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, (41 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 ￥16,820
￥50,097 total
includes taxes & fees
Jul 26 - Jul 27
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Exterior

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

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Montebello
10.0 out of 10, Exceptional, (65 reviews)
"We had a great stay at the Cabin! Everything met our expectations and more we will definitely be coming back!"
United States
Jake
The price is ￥21,208
￥34,586 total
includes taxes & fees
Jul 23 - Jul 24
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
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, (157 reviews)
"It was a beautiful stay - we enjoyed the place and wished we could have stayed one more day to soak up the surroundings of the area more!"
United States
Michelle W.
The price is ￥17,876
￥40,515 total
includes taxes & fees
Jul 29 - Jul 30
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior

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, (192 reviews)
"Excellent stay! Perfect little get-a-way cabin in the woods!"
United States
Brenda P.
The price is ￥20,564
￥26,759 total
includes taxes & fees
Aug 5 - Aug 6
Cozy cabin for 2 w/ great mt views & walking trails!
Property grounds

Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls

Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
Tyro
10.0 out of 10, Exceptional, (30 reviews)
"Everything was great! The house is well appointed and the fenced in yard was perfect for our dogs. Highly recommend."
United States
Michael W.
The price is ￥32,705
￥56,620 total
includes taxes & fees
Jul 27 - Jul 28
Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
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, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is ￥17,480
￥40,341 total
includes taxes & fees
Jul 23 - Jul 24
Escape to the Blue Ridge Mountains at Wine-tergreen!
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (35 reviews)
"Condo was as advertised, perfect for a quick trip up to Wintergreen!"
United States
Jason L.
The price is ￥18,606
￥43,256 total
includes taxes & fees
Jul 23 - Jul 24
Wintergreen Condo -Steps to Ski and restaurants
Exterior

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (119 reviews)
"Great location"
United States
Chrissy R.
The price is ￥27,174
￥52,330 total
includes taxes & fees
Aug 20 - Aug 21
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Property grounds

Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA

Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA
Roseland
10.0 out of 10, Exceptional, (35 reviews)
"The cabin was perfect for our family of four! The owner thought of all the small details that made our trip easy and accessible. We will be back! "
United States
Brittany P.
The price is ￥37,377
￥58,217 total
includes taxes & fees
Jul 28 - Jul 29
Mountain Hideaway Cabin Near Wintergreen and Rt 151 Nelson County, VA
Exterior

Mountain Retreat in Wintergreen!

Mountain Retreat in Wintergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
The price is ￥20,401
￥47,401 total
includes taxes & fees
Aug 4 - Aug 5
Mountain Retreat in Wintergreen!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Massies Mill Hotel Reviews

Afton Mountain Inn

Afton Mountain Inn

8/10 Good
"Stayed here when they first opened a couple years ago. Definitely is starting to show some wear. The pool is definitely not half as inviting as it once was… in need of a new liner and the lounge chairs have no cushions anymore so they are definitely not half as comfortable as they used to be. The fire pits have no kindling or fire starter and with no staff on site you need to figure that out on your own. The rooms are very clean, mattress is very comfy and bathroom was beautifully updated. Just need someone to do some outdoor updating and maintenance for sure!"
Seth 3-night trip
Posted 16 hours ago
Afton Mountain Inn

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:

  • View our selection of featured holiday rentals in Massies Mill
  • Use the map to find apartments and other holiday homes in the Massies Mill neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Massies Mill while they last

Look no further and take a look at our great range of rental properties in Massies Mill!

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?

Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI: This vacation home rental near 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 you can cook with friends or family. Make the most of the arcade game 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 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.