A historic brick building with columns and a central entrance.

Charlottesville Holiday Rentals

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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 Charlottesville holiday rentals

Room

1. SONSAK - MONTICELLO

SONSAK - MONTICELLO
3.5 star property
Charlottesville
10.0 out of 10, Exceptional, (12 reviews)
"Excellent For Couples Getaways!!!"
United States
Jonathan
The price is S$159
includes taxes & fees
15 Nov - 16 Nov
SONSAK - MONTICELLO
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.

2. 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$317
includes taxes & fees
11 Nov - 12 Nov
Cavalier Cocoon
A house with a stone facade, a wooden front door, and a mailbox.

3. The 1st Street Bungalow

The 1st Street Bungalow
2.0 star property
Ridge St.
The price is S$629
includes taxes & fees
7 Dec - 8 Dec
The 1st Street Bungalow
A house with a red door, a porch with two rocking chairs and a small table, and a window above the door.

4. Oasis on 5th

Oasis on 5th
2.0 star property
Fifeville
The price is S$713
includes taxes & fees
9 Dec - 10 Dec
Oasis on 5th
A spacious kitchen with wooden flooring, a dining area with a table and chairs, and a large window with a view of trees.

5. Hardwood Hall

Hardwood Hall
2.0 star property
Barracks Rugby
The price is S$1,303
includes taxes & fees
11 Nov - 12 Nov
Hardwood Hall
A two-story house with a porch and a garage, surrounded by a well-maintained lawn and trees.

6. Ranchito

Ranchito
2.0 star property
Troy
The price is S$1,321
includes taxes & fees
25 Nov - 26 Nov
Ranchito
A cabin with a fire pit, picnic table, and Adirondack chairs in a forest setting.

7. 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, (156 reviews)
"Picture perfect, seemless check in and the coffee and maple oatmeal were my cherry on top!"
United States
Rachel
The price is S$242
includes taxes & fees
9 Dec - 10 Dec
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Street view

8. 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 S$162
includes taxes & fees
24 Nov - 25 Nov
Valley Extended Suites
A fire pit with chairs, a small house with stairs, and trees in a yard.

9. Artisan's Cottage

Artisan's Cottage
2.0 star property
Afton
The price is S$382
includes taxes & fees
29 Nov - 30 Nov
Artisan's Cottage
A two-story house with a deck, large windows, and a garage.

10. 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 S$241
includes taxes & fees
29 Nov - 30 Nov
Love Ridge Mountain Lodging
An outdoor seating area with a fire pit, wicker chairs, and a view of the landscape.

11. 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$523
includes taxes & fees
15 Nov - 16 Nov
Afton Mountain Vineyards
Interior

12. Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
Nellysford
The price is S$831
includes taxes & fees
11 Nov - 12 Nov
Modern Nellysford Getaway on 40 Private Acres!
A spacious living area with a staircase, a brown leather sofa, a globe on a wooden stand, and a dining table with a tray.

13. Blue Ridge Hideaway

Blue Ridge Hideaway
2.0 star property
Waynesboro
The price is S$310
includes taxes & fees
18 Nov - 19 Nov
Blue Ridge Hideaway
A kitchen with wooden cabinets, a stainless steel refrigerator, a large island with bar stools, and pendant lighting.

14. 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)
Mountaintop Wintergreen Resort Home w/ Deck, Views
Exterior

15. The Guest Wing at Kateri

The Guest Wing at Kateri
2.0 star property
Waynesboro
10.0 out of 10, Exceptional, (1 review)
"The property was amazing, beyond wonderful. Gracious host. High end furniture and bedding. The backyard and pool area were just beautiful !!! I wish I stayed earlier in the year so i could enjoy the pool. The property is surrounded by wide open farm lands, Starry skies, birds and crickets. It was a very relaxing stay. I wish I could stay longer !!!"
United States
Barbara
The price is S$443
includes taxes & fees
16 Nov - 17 Nov
The Guest Wing at Kateri
A log cabin with a large deck, surrounded by trees.

16. Afton View Lodge

Afton View Lodge
3.0 star property
Afton
The price is S$851
includes taxes & fees
9 Dec - 10 Dec
Afton View Lodge
A modern kitchen with a large island, dark cabinetry, and a view to the dining area.

17. 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 S$574
includes taxes & fees
15 Nov - 16 Nov
Little Haven Cottage
A fire pit surrounded by black Adirondack chairs in a forested outdoor area.

18. Pine and Vine

Pine and Vine
2.0 star property
Gordonsville
The price is S$1,094
includes taxes & fees
30 Nov - 1 Dec
Pine and Vine
A wooden cabin with a sliding door, a hot tub, and string lights.

19. The Reserve at 151

The Reserve at 151
2.0 star property
Afton
10.0 out of 10, Exceptional, (1 review)
The price is S$820
includes taxes & fees
11 Nov - 12 Nov
The Reserve at 151
A cabin with a porch, surrounded by trees.

20. Nelson Cozy Cabin

Nelson Cozy Cabin
2.0 star property
Nellysford
The price is S$591
includes taxes & fees
22 Nov - 23 Nov
Nelson Cozy Cabin
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 Charlottesville Hotel Reviews

Omni Charlottesville Hotel

Omni Charlottesville Hotel

10/10 Excellent
"Very nice hotel. Recommended if you’re staying in Charlottesville."
Chris 1-night trip
Posted less than an hour ago
Omni Charlottesville Hotel

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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 182 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 Historic Court Square 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.