A historic brick building with columns and a central entrance.

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

Our top choices for Charlottesville holiday rentals

A spacious kitchen with wooden flooring, a marble island, and white cabinetry.

1. Ranchito

Ranchito
2.0 star property
Troy
The price is S$1,073
includes taxes & fees
19 Oct - 20 Oct
Ranchito

2. SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (5 reviews)
"Our stay was perfect. Hotels.com really messed up the booking and I almost didn’t have a place to stay. The host at this property held the room for me and we handled everything directly. He was great, the room was spectacular!"
United States
Crystal
The price is S$159
includes taxes & fees
28 Sept - 29 Sept
SONSAK - MONTICELLO
A spacious kitchen with wooden flooring, a dining area with a table and chairs, and a large window with a view of trees.

3. Hardwood Hall

Hardwood Hall
2.0 star property
Barracks Rugby
The price is S$1,370
includes taxes & fees
30 Sept - 1 Oct
Hardwood Hall
A spacious living area with a sofa, armchairs, a coffee table, and a TV. There is a dining area with chairs and a table. The room has a wooden floor and white walls.

4. Cavalier Cocoon

Cavalier Cocoon
2.0 star property
Jefferson Park Avenue
10.0 out of 10, Exceptional, (1 review)
"Love this place! It’s close to campus as well as some great food. Don’t miss Pi Napo for pizza. We stayed at the end of a long road trip so we appreciated the washer and dryer."
United States
Lisa
The price is S$291
includes taxes & fees
28 Sept - 29 Sept
Cavalier Cocoon
A bathroom with a white sink, a chrome faucet, a soap dispenser, and a toilet paper holder.

5. Riverbluff Nest

Riverbluff Nest
2.0 star property
Woolen Mills
The price is S$438
includes taxes & fees
19 Oct - 20 Oct
Riverbluff Nest
A house with a red door, a porch with two rocking chairs and a small table, and a window above the door.

6. Oasis on 5th

Oasis on 5th
2.0 star property
Fifeville
The price is S$740
includes taxes & fees
28 Sept - 29 Sept
Oasis on 5th

7. 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 S$149
includes taxes & fees
20 Oct - 21 Oct
Valley Extended Suites
A cabin with a dining table set for a meal, a bicycle, and a sign indicating the name 'Vangelis'.

8. Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
2.5 star property
Stanardsville
9.4 out of 10, Exceptional, (143 reviews)
"Loved everything about my stay, customer service was amazing and I’m definitely making this an animal visit!"
United States
Promise
The price is S$242
includes taxes & fees
30 Sept - 1 Oct
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

9. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
The price is S$351
includes taxes & fees
27 Oct - 28 Oct
Three Little Bears
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.

10. 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 S$169
includes taxes & fees
13 Oct - 14 Oct
Affordable Suites of America Waynesboro
A two-story house with a deck, large windows, and a garage.

11. Love Ridge Mountain Lodging

Love Ridge Mountain Lodging
3.0 star property
Lyndhurst
10.0 out of 10, Exceptional, (25 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 S$263
includes taxes & fees
30 Sept - 1 Oct
Love Ridge Mountain Lodging

12. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is S$832
includes taxes & fees
6 Oct - 7 Oct
Modern Nellysford Getaway on 40 Private Acres!
A bedroom with a large bed, a ceiling fan, and two windows with blinds.

13. 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 S$560
includes taxes & fees
28 Sept - 29 Sept
Afton Mountain Vineyards
A wooden deck with wicker furniture, a brick wall, and a view of greenery.

14. Bluebird Cottage

Bluebird Cottage
2.0 star property
Roseland
The price is S$345
includes taxes & fees
28 Sept - 29 Sept
Bluebird Cottage
A cabin with a porch, surrounded by trees.

15. Nelson Cozy Cabin

Nelson Cozy Cabin
2.0 star property
Nellysford
The price is S$550
includes taxes & fees
28 Sept - 29 Sept
Nelson Cozy Cabin
A modern living room with a large sectional sofa, a fireplace, and a view of the mountains.

16. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is S$438
includes taxes & fees
27 Sept - 28 Sept
Firefly on The Ridge
A hot tub with a wooden deck and a view of a forest.

17. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is S$556
includes taxes & fees
28 Sept - 29 Sept
Bear Tracks Cottage
A living room with a brown leather sofa, a grey armchair, a round woven ottoman, a patterned rug, a white table with chairs, and a painting on the wall.

18. Blue Ridge Hideaway

Blue Ridge Hideaway
2.0 star property
Waynesboro
The price is S$289
includes taxes & fees
28 Sept - 29 Sept
Blue Ridge Hideaway
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.

19. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
The price is S$329
includes taxes & fees
27 Sept - 28 Sept
Mountain View Vista
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

20. Panoramic Peak

Panoramic Peak
2.0 star property
Nellysford
The price is S$329
includes taxes & fees
28 Sept - 29 Sept
Panoramic Peak
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 Charlottesville Hotel Reviews

English Inn of Charlottesville

English Inn of Charlottesville

8/10 Good
"The room was clean and well maintained and the staff was friendly and helpful. The breakfast bar was good and had a decent selection to choose from. I enjoyed my stay. I would stay again"
Alicia 4-night trip
Posted 3 hours ago
English Inn of Charlottesville

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Charlottesville?

Yes, there are holiday rentals in Charlottesville close to Carter Mountain Orchard, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Charlottesville like the majestic mountain landscape and great live music this destination is known for. While you're here, don't miss the university campus and array of shops.

What are some of the best holiday rentals that Charlottesville has to offer?

Massanutten Resort by Tripforth: This holiday home rental outside Charlottesville is located near skiing, and has an outdoor pool, an arcade/games room and free WiFi to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Charlottesville?

With 188 Expedia holiday rentals, you're guaranteed to find just the right place for your Charlottesville stay.

What’s there to see and do in Charlottesville?

Family-friendly attractions include Virginia Discovery Museum and Charlottesville Ice Park, whereas Carter Mountain Orchard and Ix Art Park are a couple of great spots to enjoy the outdoors. While here, Ting Pavilion and Downtown Mall are other places worth a visit.

What’s a holiday rental in Charlottesville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charlottesville. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family getaway.