A mountainous landscape with autumn foliage.

Lovingston 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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Lovingston 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, (30 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
The price is SAR 374
SAR 645 total
includes taxes & fees
10 Dec - 11 Dec
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
The price is SAR 662
SAR 1,586 total
includes taxes & fees
12 Nov - 13 Nov
Blackwood Chalet
Interior

3. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is SAR 1,025
SAR 2,440 total
includes taxes & fees
12 Nov - 13 Nov
Modern Nellysford Getaway on 40 Private Acres!
Street view

4. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (282 reviews)
"Clean room convenient parking, good kitchen, friendly staff."
United States
Jamie
The price is SAR 428
SAR 476 total
includes taxes & fees
15 Nov - 16 Nov
Valley Extended Suites
An outdoor seating area with a fire pit, wicker chairs, and a view of the landscape.

5. 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
The price is SAR 1,367
SAR 1,535 total
includes taxes & fees
15 Nov - 16 Nov
Afton Mountain Vineyards
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

6. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is SAR 511
SAR 1,100 total
includes taxes & fees
12 Nov - 13 Nov
Bluebird Cottage
A kitchen with wooden cabinets, a stainless steel refrigerator, a large island with bar stools, and pendant lighting.

7. Mountaintop Wintergreen Resort Home w/ Deck, Views

Mountaintop Wintergreen Resort Home w/ Deck, Views
3.0 star property
Nellysford
10.0 out of 10, Exceptional, (1 review)
The price is SAR 796
SAR 1,899 total
includes taxes & fees
23 Nov - 24 Nov
Mountaintop Wintergreen Resort Home w/ Deck, Views
A hallway with a wooden staircase, a bench, and a door leading to a balcony.

8. Fore Seasons

Fore Seasons
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (1 review)
"Me and my family had such a great time. The house was clean and beautiful. Everything about the house was amazing. The hosts were very responsive and sincere.❤️"
United States
Menen
The price is SAR 622
SAR 1,204 total
includes taxes & fees
12 Nov - 13 Nov
Fore Seasons
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

9. 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
The price is SAR 617
SAR 1,073 total
includes taxes & fees
12 Nov - 13 Nov
Panoramic Peak
A sauna with wooden benches and a view of a forested hillside.

10. Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is SAR 666
SAR 1,233 total
includes taxes & fees
1 Dec - 2 Dec
Branch and Barrel
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

11. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
The price is SAR 489
SAR 1,181 total
includes taxes & fees
12 Nov - 13 Nov
Three Little Bears
A two-story cabin with a deck and outdoor seating area.

12. On Mountain Time

On Mountain Time
2.5 star property
Roseland
The price is SAR 1,328
SAR 2,861 total
includes taxes & fees
16 Nov - 17 Nov
On Mountain Time
A wooden cabin with a stone exterior, a balcony with wooden railings, and outdoor seating with Adirondack chairs.

13. Tucked Inn: Lower Unit

Tucked Inn: Lower Unit
2.0 star property
Nellysford
The price is SAR 444
SAR 1,131 total
includes taxes & fees
12 Nov - 13 Nov
Tucked Inn: Lower Unit
A string of lights hanging outdoors, with a wooden structure and a view of a forested landscape in the background.

14. Hillside Haven

Hillside Haven
2.0 star property
Faber
The price is SAR 795
SAR 1,525 total
includes taxes & fees
30 Nov - 1 Dec
Hillside Haven
A hot tub with a wooden deck and a view of a forest.

15. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is SAR 813
SAR 1,671 total
includes taxes & fees
12 Nov - 13 Nov
Bear Tracks Cottage
A wooden cabin with a sliding door, a hot tub, and string lights.

16. The Reserve at 151

The Reserve at 151
2.0 star property
Afton
10.0 out of 10, Exceptional, (1 review)
The price is SAR 1,017
SAR 2,407 total
includes taxes & fees
16 Nov - 17 Nov
The Reserve at 151
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
The price is SAR 466
SAR 1,156 total
includes taxes & fees
16 Nov - 17 Nov
Tucked Inn: Upper Unit
A modern kitchen with a large island, dark cabinetry, and a view to the dining area.

18. 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
The price is SAR 751
SAR 1,686 total
includes taxes & fees
15 Nov - 16 Nov
Little Haven Cottage
Lounge

19. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is SAR 799
SAR 1,425 total
includes taxes & fees
12 Nov - 13 Nov
Firefly on The Ridge
A two-story cabin with a balcony, surrounded by trees.

20. Blackrock Canopy

Blackrock Canopy
2.0 star property
Nellysford
The price is SAR 1,197
SAR 2,925 total
includes taxes & fees
12 Nov - 13 Nov
Blackrock Canopy
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 Lovingston Hotel Reviews

Grey Pine Lodge

Grey Pine Lodge

10/10 Excellent
"It was a very pleasant stay. The room was nice. My only complaint would be that there was no ice machine. Also if you need anything there is no staff present. Such as towels. Fortunately I was good with what I had."
Dwayne 4-night trip
Posted 1 day ago
Grey Pine Lodge

Frequently asked questions

Can I find a vacation rental in Lovingston?

Yes, we offer vacation rentals near the most popular attractions in Lovingston, or you can go with a more secluded option if you're looking for relaxation. Visitors to Lovingston speak positively about the mountain landscape and wineries in this destination. Make sure you have time to check out the coffeehouses and jazz scene during your trip.

What are some of the best vacation home rentals that Lovingston has to offer?

Wintergreen cabin, hot tub, sauna, walk to trails: This vacation home rental outside of Lovingston 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.

How many vacation rentals are there in Lovingston?

Choose from 4 Expedia vacation rentals in Lovingston for a memorable vacation.

What’s there to see and do in Lovingston?

Naked Mountain State Natural Area Preserve and Fortune's Cove Preserve are a couple of lovely local spots to get outside and enjoy nature. While here, Lovingston Winery and Virginia Distillery Museum are other places worth a visit.

What’s a vacation rental in Lovingston like?

Vacation rentals are private properties you can stay in for several days or longer in Lovingston. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for small groups.