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Massies Mill Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Massies Mill vacation rentals

A two-story house with a deck, large windows, and a garage.

1. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
9.6 out of 10, Exceptional, (29 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
$186 nightly
The price is $202
Nov 18 - Nov 19
Total with taxes and fees
Love Ridge Mountain Lodging
A spacious living area with a wooden staircase, a dining table, and a sofa.

2. Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (6 reviews)
"Cleanliness and ease of check in"
United States
Patrick
$376 nightly
The price is $423
Nov 5 - Nov 6
Total with taxes and fees
Blackwood Chalet
Interior

3. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
$579 nightly
The price is $650
Nov 9 - Nov 10
Total with taxes and fees
Modern Nellysford Getaway on 40 Private Acres!
An outdoor seating area with a fire pit, wicker chairs, and a view of the landscape.

4. Afton Mountain Vineyards

Afton Mountain Vineyards
3.5 star property
Afton
7.4 out of 10, Good, (3 reviews)
"Cozy and comfortable with pond and mountain views. Wine tasting on site and easy access to Wintergreen. We loved our stay and will be back again!"
United States
Jennifer
$405 nightly
The price is $454
Nov 15 - Nov 16
Total with taxes and fees
Afton Mountain Vineyards
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

5. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
$261 nightly
The price is $293
Nov 5 - Nov 6
Total with taxes and fees
Bluebird Cottage
A wooden structure with a large glass door, a gravel patio, outdoor furniture, and a view of trees and hills.

6. Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
$293 nightly
The price is $329
Nov 5 - Nov 6
Total with taxes and fees
Branch and Barrel
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

7. Panoramic Peak

Panoramic Peak
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (1 review)
"The place was absolutely beautiful and spotless. The view was amazing. The only issue we had was when we asked where it was. We were told Nellysford and didn’t really understand that it was part of the Wintergreen resort so it was much further away from our actual destination. But the place was really amazing. We would stay there again."
United States
Carrie
$254 nightly
The price is $286
Nov 23 - Nov 24
Total with taxes and fees
Panoramic Peak
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

8. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
$280 nightly
The price is $315
Nov 5 - Nov 6
Total with taxes and fees
Three Little Bears
A two-story cabin with a deck and outdoor seating area.

9. On Mountain Time

On Mountain Time
2.5 star property
Roseland
$679 nightly
The price is $762
Nov 9 - Nov 10
Total with taxes and fees
On Mountain Time
A two-story cabin with a balcony, surrounded by trees.

10. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
$688 nightly
The price is $773
Nov 16 - Nov 17
Total with taxes and fees
Blackrock Canopy
Lounge

11. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
$339 nightly
The price is $381
Nov 24 - Nov 25
Total with taxes and fees
Firefly on The Ridge
A wooden cabin with a sliding door, a hot tub, and string lights.

12. The Reserve at 151

The Reserve at 151
2.0 star property
Afton
10.0 out of 10, Exceptional, (1 review)
$571 nightly
The price is $641
Nov 9 - Nov 10
Total with taxes and fees
The Reserve at 151
A modern kitchen with a large island, dark cabinetry, and a view to the dining area.

13. Little Haven Cottage

Little Haven Cottage
2.0 star property
Afton
8.0 out of 10, Very good, (1 review)
"Good location, very spacious for 4 guests. Excellent choice of LVP flooring instead of carpeting as there was significant rainfall both days of the visit that would have suffered wet shoes on departures and arrivals at the house."
United States
Elizabeth
$400 nightly
The price is $449
Nov 5 - Nov 6
Total with taxes and fees
Little Haven Cottage
A fire pit with chairs, a small house with stairs, and trees in a yard.

14. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
$266 nightly
The price is $299
Nov 9 - Nov 10
Total with taxes and fees
Artisan's Cottage
A wooden cabin with a stone exterior, a balcony with wooden railings, and outdoor seating with Adirondack chairs.

15. Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
$268 nightly
The price is $301
Nov 5 - Nov 6
Total with taxes and fees
Tucked Inn: Lower Unit
Exterior

16. Art & Soul

Art & Soul
2.0 star property
Nellysford
$700 nightly
The price is $786
Nov 15 - Nov 16
Total with taxes and fees
Art & Soul
A wooden deck with a yellow door, a table with chairs, and a rocking chair.

17. Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
$274 nightly
The price is $308
Nov 9 - Nov 10
Total with taxes and fees
Tucked Inn: Upper Unit
A hot tub with a wooden deck and a view of a forest.

18. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
$397 nightly
The price is $445
Nov 16 - Nov 17
Total with taxes and fees
Bear Tracks Cottage
A two-story stone house with a deck, outdoor seating, and a fireplace.

19. Red White and Wintergreen

Red White and Wintergreen
2.0 star property
Pedlars Edge
$883 nightly
The price is $991
Nov 5 - Nov 6
Total with taxes and fees
Red White and Wintergreen
A wooden deck with outdoor seating and a fire pit.

20. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
$496 nightly
The price is $557
Nov 9 - Nov 10
Total with taxes and fees
Mountain Mindset
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

Love Ridge Mountain Lodging

Love Ridge Mountain Lodging

10/10 Excellent
"We had a great overnight stay. Loved exploring the wooded grounds, watched a beautiful sunset at 5 min drive overlook on the Blue Ridge parkway, had marshmallows toasted over a fire & did some stargazing from right outside our cabin, then hiked in the area the next morning. Loved meeting the sweet property kitty. Only wish we had more time to check out the game shed and try some disc golf there. Clean & comfy. Overall a perfect stay!"
Anonymous traveler 1-night trip
Posted 8 hours ago
Love Ridge Mountain Lodging

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 $171 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?

Wintergreen cabin, hot tub, sauna, walk to trails: This vacation home rental near Massies Mill is located in the mountains and has a fireplace, a balcony, 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 Oak Ridge Estate 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.