A mountainous landscape with autumn foliage.

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Lovingston condo rentals

A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

1. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (59 reviews)
$166 nightly
The price is $187
Aug 31 - Sep 1
Total with taxes and fees
Where the Trail Ends
A garden with a variety of flowers and trees at dusk.

2. 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
Aug 30 - Aug 31
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

3. 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, (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
Aug 29 - Aug 30
Total with taxes and fees
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

4. 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
Aug 30 - Aug 31
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A wooden deck with a round table and chairs, overlooking a grassy area with trees.

5. 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.
$230 nightly
The price is $258
Aug 30 - Aug 31
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
A house with a covered porch, two Adirondack chairs, and a welcome mat.

6. Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (5 reviews)
"The place was great and we enjoyed our stay! Super comfy and cozy. Would definitely stay again!"
United States
Christopher H.
$286 nightly
The price is $290
Aug 30 - Aug 31
Total with taxes and fees
Cozy Lux Condo at Wintergreen Resort
A hotel room with a large bed, a desk, a chair, a lamp, and a view of the outdoor deck.

7. 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.
$227 nightly
The price is $255
Sep 1 - Sep 2
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

8. 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.
$239 nightly
The price is $268
Aug 31 - Sep 1
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
A swimming pool surrounded by lush greenery and a wooden cabin.

9. 2BR/2BA + Bonus Kids Room. Walk to Slopes, Village & Market. Pool. Dog-Friendly.

2BR/2BA + Bonus Kids Room. Walk to Slopes, Village & Market. Pool. Dog-Friendly.
Wintergreen Resort
10.0 out of 10, Exceptional, (4 reviews)
"This is a warm and inviting condo. We enjoyed our stay. The host provided excellent communication!"
United States
Shannon T.
$301 nightly
The price is $337
Aug 31 - Sep 1
Total with taxes and fees
2BR/2BA + Bonus Kids Room. Walk to Slopes, Village & Market. Pool. Dog-Friendly.
A wooden deck with two Adirondack chairs facing a scenic view of a sunset over a mountainous landscape.

10. 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, (119 reviews)
"Gorgeous views! We spent most of our time out and about, but enjoyed our stay!"
United States
Jennifer P.
$232 nightly
The price is $261
Aug 31 - Sep 1
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!
A kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a granite countertop.

11. Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (15 reviews)
"The condo was beautiful and clean and worked perfectly for our group."
United States
Eric W.
$292 nightly
The price is $328
Aug 29 - Aug 30
Total with taxes and fees
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

12. Mountain Inn Studio 96 with Wintergreen Advantage

Mountain Inn Studio 96 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. "
United States
Lana
$241 nightly
The price is $270
Aug 31 - Sep 1
Total with taxes and fees
Mountain Inn Studio 96 with Wintergreen Advantage

13. Timbers Studio 46 with Wintergreen Advantage

Timbers Studio 46 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple...
United States
Madison D.
$241 nightly
The price is $270
Aug 31 - Sep 1
Total with taxes and fees
Timbers Studio 46 with Wintergreen Advantage
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

14. Panoramic Peak

Panoramic Peak
2.0 star property
Nellysford
$229 nightly
The price is $257
Sep 13 - Sep 14
Total with taxes and fees
Panoramic Peak

15. Mountain Inn Lodge 57 with Wintergreen Advantage

Mountain Inn Lodge 57 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
$265 nightly
The price is $297
Aug 31 - Sep 1
Total with taxes and fees
Mountain Inn Lodge 57 with Wintergreen Advantage
A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

16. 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
Aug 30 - Aug 31
Total with taxes and fees
Mountain Retreat in Wintergreen!
A two-story log cabin with a balcony, a staircase, and a snow-covered roof.

17. Pet-Friendly Retreat Walk to Slopes & Village!

Pet-Friendly Retreat Walk to Slopes & Village!
Wintergreen Resort
10.0 out of 10, Exceptional, (1 review)
"A wonderful place to stay comfortable beds. The place was nice and clean "
United States
Denise P.
$260 nightly
The price is $292
Aug 31 - Sep 1
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!
A modern kitchen with white cabinetry, a black stove, and a dining area with a chandelier.

18. Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf

Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"Pet-friendly, very hospitable, had coffee and Brita filter for water, linens, paper towels, everything we needed. "
United States
Sarah L.
$265 nightly
The price is $298
Aug 31 - Sep 1
Total with taxes and fees
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
A mountainous landscape with dense green forests and a clear sky.

19. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (330 reviews)
"Our 2-BR condo was lovely. Everything was sparkling clean and the place was spacious for what we needed. What MADE it, though, was the VIEW which was spectacular! I felt we should have been pre-informed that there was no coffee for us to use. We could have easily brought some but didn’t know of its non-existence."
United States
Virginia
$229 nightly
The price is $257
Sep 27 - Sep 28
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A modern kitchen with white cabinetry, a large island with bar stools, stainless steel appliances, and a chandelier.

20. Your Ski-In and Ski-Out Wintergreen Escape

Your Ski-In and Ski-Out Wintergreen Escape
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place!"
United States
Chris C.
$299 nightly
The price is $336
Aug 31 - Sep 1
Total with taxes and fees
Your Ski-In and Ski-Out Wintergreen Escape
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 Lovingston Hotel Reviews

The Crossroads Inn

The Crossroads Inn

10/10 Excellent
"It was such a beautiful, historic site to stay. It was centrally located to everything we wanted to do hiking, tubing, sightseeing. The breakfast was outstanding. The vineyard next door is one of the best places I have ever eaten."
Angie 4-night trip
Posted 1 hour ago
The Crossroads Inn

Find out more about Lovingston

Lovingston Condo Rentals information

Number of reviews
966
Accommodation
336 Condo Rentals
Lowest Price
$187
Highest Price
$337

Frequently asked questions

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What is there to do in Lovingston near my condo?
If you're eager to see the sights of Lovingston, pay a visit to Lovingston Winery. It's popular among travelers and locals alike.

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