Search Holiday Rentals in Charlottesville

    price find illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Save instantly and earn perks with One Key
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Top Holiday Rentals in Charlottesville

Charming Updated 3 Bedroom Home Near Downtown

9.8 out of 10, Exceptional, (54)
"Super accommodating host and very nice property— clean and comfortable. "
The price is £328
includes taxes & fees
2 Jul - 3 Jul
Charming Updated 3 Bedroom Home Near Downtown

Historic Beauty and Walkable to Everywhere

10.0 out of 10, Exceptional, (48)
"We really enjoyed our stay here. The house was wonderful, very nicely decorated and clean. We really liked how close it was to all the unique restaurants and downtown.Nightlife"
The price is £266
includes taxes & fees
30 Jul - 31 Jul
Historic Beauty and Walkable to Everywhere

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (78)
"We absolutely loved our stay here! Absolutely beautiful property inside and out, perfect cozy spot, caught the snow which was beautiful! Only 15 minutes from town. We will definitely be back, and we loved the Alley Light suggestion from the owner which was incredible! All around it was a perfect stay, thank you!"
1802 cottage once part of Monticello and owned by Thomas Jefferson

Charlottesville Retreat for Family & Friends

10.0 out of 10, Exceptional, (98)
"Loved our time here. The house was cozy, outdoors peaceful and quiet. Would highly recommend to anyone visiting the area. Great for large groups too!"
Charlottesville Retreat for Family & Friends

Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi

2.0 star property
8.8 out of 10, Excellent, (6)
"Stayed here for one night for a concert at JPJ. Perfect location, cute and clean house, snacks & coffee there when we arrived, easy access and great communication! "
The price is £248
includes taxes & fees
9 Jul - 10 Jul
Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi

Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!

9.8 out of 10, Exceptional, (83)
"Perfectly located for dinners in historic district and visiting wine country."
The price is £234
includes taxes & fees
14 Jul - 15 Jul
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (52)
"The cottage was super adorable and perfect for our little weekend getaway!!! "
The price is £258
includes taxes & fees
7 Jul - 8 Jul
Ivy Rose Cottage nestled b/t Cville & Vineyards

Postcard Cabins Shenandoah

2.0 star property
10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay. Real close to Shenandoah National Park. "
The price is £144
includes taxes & fees
2 Jul - 3 Jul
Postcard Cabins Shenandoah

Massanutten's Woodstone Meadows by Tripforth

4.0 star property
9.0 out of 10, Wonderful, (216)
"Nice and quiet place to stay over the weekend and food was great "
Massanutten's Woodstone Meadows by Tripforth

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (188)
"I liked that it's has regular door keys. Loved it!"
The price is £80
includes taxes & fees
6 Jul - 7 Jul
Valley Extended Suites

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

9.0 out of 10, Wonderful, (282)
"The condo has just the right amenities, nicely decorated, and yes, a million dollar view."
The price is £179
includes taxes & fees
9 Jul - 10 Jul
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Massanutten Resort by Tripforth

3.0 star property
7.8 out of 10, Good, (152)
"The condo was very nice and clean. It accommodated our needs for the weekend. "
Massanutten Resort by Tripforth

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

9.0 out of 10, Wonderful, (111)
"Owners were easy to reach and very kind!! Place was clean and easy to locate. Everything about it rocked!"
The price is £149
includes taxes & fees
10 Jul - 11 Jul
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

Afton Mountain Vineyards

2.5 star property
The price is £276
includes taxes & fees
2 Jul - 3 Jul
Afton Mountain Vineyards

Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries.

10.0 out of 10, Exceptional, (31)
"We had a beautiful stay and very secluded. We would love to come back. "
Cozy Cabin located close to Shenandoah National Park, Wineries, and Breweries.

The Summit at Massanutten Resort by Tripforth

3.5 star property
9.2 out of 10, Wonderful, (60)
"Great location and it was quiet and clean. Easy check in"
The Summit at Massanutten Resort by Tripforth

Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

10.0 out of 10, Exceptional, (55)
"Totally enjoyed our stay here. Loved sitting outside listening to the water going down the creek. House was clean and located in a quiet neighborhood. "
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead

Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing

9.0 out of 10, Wonderful, (141)
"Evidently rustic means trashy, trash all around the property trees, falling all over the place, just waiting for the next one to fall through the cabin not as advertised took forever to get into the cabin because things were taken care of properly"
Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (307)
"The house is so nice, and area is gorgeous. We do an annual girls trip, and this was perfect for us. Walking distance to a store was nice as well. The owners were only a text away if we needed anything, but we didn't. Highlyrecommend. "
The price is £280
includes taxes & fees
14 Jul - 15 Jul
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed

10.0 out of 10, Exceptional, (56)
"Enjoyed our stay at this lovely getaway - clean, pleasant and roomy home. "
The price is £316
includes taxes & fees
9 Jul - 10 Jul
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
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.
Save an average of 15% on thousands of hotels when you're signed in

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 acclaimed theatre scene 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's Woodstone Meadows by Tripforth: This holiday home rental outside Charlottesville is located near skiing, and has an outdoor pool, an arcade/games room and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Some other homes for rent in Charlottesville include Historic Beauty and Walkable to Everywhere and Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi.

How many holiday rentals will I find in Charlottesville?

With 173 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 Charlottesville Ice Park and Virginia Discovery Museum, 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.