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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Lovingston vacation rentals

A sauna with wooden benches and a view of a forested hillside.

1. Branch and Barrel

Branch and Barrel
2.0 star property
Roseland
The price is P9,407
P17,607 total
includes taxes & fees
Sep 24 - Sep 25
Branch and Barrel
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, (24 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 P8,796
P13,640 total
includes taxes & fees
Sep 24 - Sep 25
Love Ridge Mountain Lodging
A compact kitchen with a stove, a dining area with chairs and a table, and a small seating area with a sofa and a lamp.

3. Affordable Suites of America Waynesboro

Affordable Suites of America Waynesboro
2.5 star property
Waynesboro
9.0 out of 10, Wonderful, (70 reviews)
"Very good value, would definitely stay again"
United States
Frank
The price is P6,209
P6,910 total
includes taxes & fees
Sep 24 - Sep 25
Affordable Suites of America Waynesboro

4. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is P17,121
P40,767 total
includes taxes & fees
Oct 6 - Oct 7
Modern Nellysford Getaway on 40 Private Acres!

5. Valley Extended Suites

Valley Extended Suites
3.0 star property
Fishersville
9.0 out of 10, Wonderful, (258 reviews)
"Would stay again 👍"
United States
Jessica
The price is P7,150
P7,957 total
includes taxes & fees
Sep 29 - Sep 30
Valley Extended Suites
A bedroom with a large bed, a ceiling fan, and two windows with blinds.

6. 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 P24,471
P27,481 total
includes taxes & fees
Sep 24 - Sep 25
Afton Mountain Vineyards
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

7. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is P7,212
P16,904 total
includes taxes & fees
Sep 28 - Sep 29
Bluebird Cottage
A bedroom with a bed, a television, a mirror, and a staircase leading to another room.

8. On Mountain Time

On Mountain Time
2.5 star property
Roseland
The price is P18,752
P43,948 total
includes taxes & fees
Sep 24 - Sep 25
On Mountain Time
A spacious living area with a wooden staircase, a dining table, and a sofa.

9. 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 P10,599
P25,988 total
includes taxes & fees
Sep 24 - Sep 25
Blackwood Chalet
A hallway with a wooden staircase, a bench, and a door leading to a balcony.

10. Fore Seasons

Fore Seasons
2.0 star property
Nellysford
"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 P8,780
P18,312 total
includes taxes & fees
Sep 30 - Oct 1
Fore Seasons
A string of lights hanging outdoors, with a wooden structure and a view of a forested landscape in the background.

11. Hillside Haven

Hillside Haven
2.0 star property
Faber
The price is P13,045
P25,213 total
includes taxes & fees
Oct 19 - Oct 20
Hillside Haven
A wooden deck with a yellow door, a table with chairs, and a rocking chair.

12. Tucked Inn: Upper Unit

Tucked Inn: Upper Unit
2.0 star property
Nellysford
Tucked Inn: Upper Unit
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 P6,272
P17,607 total
includes taxes & fees
Sep 24 - Sep 25
Tucked Inn: Lower Unit
A wooden cabin with a sliding door, a hot tub, and string lights.

14. The Reserve at 151

The Reserve at 151
2.0 star property
Afton
10.0 out of 10, Exceptional, (1 review)
The Reserve at 151
A cabin with a porch, surrounded by trees.

15. Nelson Cozy Cabin

Nelson Cozy Cabin
2.0 star property
Nellysford
The price is P11,853
P25,637 total
includes taxes & fees
Sep 29 - Sep 30
Nelson Cozy Cabin
A hot tub with a wooden deck and a view of a forest.

16. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is P13,296
P27,608 total
includes taxes & fees
Sep 29 - Sep 30
Bear Tracks Cottage
A modern cabin with a stone chimney, large windows, a deck with outdoor furniture, and a staircase leading to an upper level.

17. Pilotview Hollow

Pilotview Hollow
2.0 star property
Nellysford
Pilotview Hollow
A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

18. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
The price is P9,658
P17,185 total
includes taxes & fees
Oct 5 - Oct 6
Mountain View Vista
A modern living room with a large sectional sofa, a fireplace, and a view of the mountains.

19. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is P11,289
P21,481 total
includes taxes & fees
Sep 24 - Sep 25
Firefly on The Ridge
A wooden deck with outdoor seating and a fire pit.

20. Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
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.
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

Spark by Hilton Waynesboro

Spark by Hilton Waynesboro

10/10 Excellent
"The staff was very friendly and helpful. The property was very clean and well maintained. This is obviously not a luxury property but it was perfect for one night as I had an appointment at UVA. Very well located to restaurants."
Elizabeth 1-night trip
Posted 3 hours ago
Spark by Hilton Waynesboro

Find out more about Lovingston

Search for holiday rentals in Lovingston on Expedia! You can easily find your home rentals, villas, holiday apartments in Lovingston using one of the methods below:

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

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

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.

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.