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Massies Mill Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Massies Mill vacation rentals

A wooden deck with a blue planter table holding a yellow flower pot.

1. Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (17 reviews)
"Great location quiet area"
United States
Scott P.
$259 nightly
The price is $290
Sep 7 - Sep 8
Total with taxes and fees
Historic Bungalow 30 minutes from Wintergreen
A two-story house with a deck, large windows, and a garage.

2. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (23 reviews)
"This place was excellent. Very clean and quiet. Sherando lake was only 4 miles away with great hiking trails. The beds were very comfortable. Would definitely stay at this place again."
United States
Josh
$188 nightly
The price is $204
Oct 6 - Oct 7
Total with taxes and fees
Love Ridge Mountain Lodging
A sandy beach with a lake and forested hills in the background.

3. 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
$220 nightly
The price is $247
Sep 15 - Sep 16
Total with taxes and fees
Cozy Country small two bedroom home.
A sauna with wooden benches and a view of a forested hillside.

4. Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
$250 nightly
The price is $281
Sep 28 - Sep 29
Total with taxes and fees
Branch and Barrel
A cozy room with a wooden ceiling, a ceiling fan, a sofa with floral cushions, a glass coffee table, and a chair.

5. 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, (114 reviews)
"Beautiful, peaceful and all accommodations were available. Very neat, meticulously cared for and we felt like we were at home."
United States
Jason L.
$175 nightly
The price is $197
Sep 10 - Sep 11
Total with taxes and fees
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

6. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (60 reviews)
"Nice resort"
United States
Diana J.
$156 nightly
The price is $175
Sep 9 - Sep 10
Total with taxes and fees
Where the Trail Ends
A small, single-story cabin with a porch and large windows, surrounded by trees.

7. 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
$188 nightly
The price is $211
Sep 7 - Sep 8
Total with taxes and fees
New cabin 1 mile from Blue Ridge Parkway. Minutes from Appalachian Trail
A garden with a variety of flowers and trees at dusk.

8. 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, (159 reviews)
"We had a calm and relaxing mountain get a way. The property was charming and perfect for us, clean and organized. The location was great. We loved to go for walks nearby and visit the gnomes and fairies in the trees. We would love to make it an annual trip and would definitely stay here again."
United States
Michelle
$223 nightly
The price is $250
Sep 7 - Sep 8
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A stone wall, a small stream, and a house with a red roof.

9. 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, (32 reviews)
"Amazing haven in a quaint setting. Can’t wait to escape here again ! "
United States
Nicole B.
$310 nightly
The price is $348
Sep 7 - Sep 8
Total with taxes and fees
Creekfront Cabin • Fire Pit • Fenced Yard • Near Crabtree Falls
A kitchenette with a coffee machine, mugs, and a sign on the wall.

10. Whole House

Whole House
Amherst
9.6 out of 10, Exceptional, (43 reviews)
"House was perfect for overnight stay. 30 min from Vines Center and easy to find."
United States
Unspecified U.
$135 nightly
The price is $149
Sep 7 - Sep 8
Total with taxes and fees
Whole House
A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

11. 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, (34 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
$190 nightly
The price is $213
Sep 7 - Sep 8
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A rustic wooden cabin with a sign reading "Rusty's Retreat." It features large windows, a door, and is surrounded by a garden with plants and a large tree.

12. Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
Afton
9.6 out of 10, Exceptional, (18 reviews)
"Beautiful little spot. We will definitely be back."
United States
Caitlin S.
$153 nightly
The price is $169
Sep 7 - Sep 8
Total with taxes and fees
Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat
A small cabin with a porch, surrounded by trees.

13. 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, (71 reviews)
"We had a great stay at the Cabin! Everything met our expectations and more we will definitely be coming back!"
United States
Jake
$203 nightly
The price is $228
Sep 10 - Sep 11
Total with taxes and fees
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
A small, dark-colored cabin with a wooden deck and large windows, surrounded by trees.

14. 5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Montebello
10.0 out of 10, Exceptional, (29 reviews)
"The cabins were well stocked and arranged to look at your window at the creek. Beautiful place to relax. Nice fire pit and pretty pollinator garden in the front. Easy place to stay and hike on the parkway. Dogs were very comfortable in the cabin. Would definitely return."
United States
alisa c.
$188 nightly
The price is $211
Sep 7 - Sep 8
Total with taxes and fees
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
A small cabin with a wooden deck, large windows, and a porch.

15. New Blue RIdge Mountains Montebello, Virginia with stary stary skies

New Blue RIdge Mountains Montebello, Virginia with stary stary skies
Montebello
10.0 out of 10, Exceptional, (23 reviews)
"Place was great! Perfect getaway. "
United States
Bradley P.
$188 nightly
The price is $211
Sep 7 - Sep 8
Total with taxes and fees
New Blue RIdge Mountains Montebello, Virginia with stary stary skies
A hotel room with a large bed, a desk, a chair, a lamp, and a view of the outdoor deck.

16. First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (17 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
$222 nightly
The price is $250
Sep 9 - Sep 10
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

17. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Wintergreen Resort
10.0 out of 10, Exceptional, (42 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
$279 nightly
The price is $313
Sep 7 - Sep 8
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

18. 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.
$286 nightly
The price is $290
Sep 7 - Sep 8
Total with taxes and fees
Mountain Retreat in Wintergreen!
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

19. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (34 reviews)
"Everything was great! Very accommodating host and lovely place!"
United States
Jason S.
$228 nightly
The price is $256
Sep 7 - Sep 8
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

20. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay for our family of 4 for a wedding weekend. Easy check-in and close to the Inn."
United States
Scott M.
$238 nightly
The price is $267
Sep 8 - Sep 9
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
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

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

10/10 Excellent
"Nice new cabin. Beautiful creek right in the back. Great location also."
GLENN R. 3-night trip
Posted 9 hours ago
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

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 $179 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?

Berry Hill Lake - Private Luxury Family Resort w/ Pool & Hot Tub - Pet Friendly: This vacation home rental near Massies Mill is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Bold Rock Hard Cider Nellysford Cidery.

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.