Charlottesville Holiday Rentals

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Holiday Rentals in Charlottesville

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (35)
"Nice quaint cottage. Exactly as described. Quick and friendly communication. "
The price is AU$580
includes taxes & fees
5 Jan - 6 Jan 2025
Ivy Rose Cottage nestled b/t Cville & Vineyards

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

10.0 out of 10, Exceptional, (232)
"We had a total of 8 adults stay at this site, to celebrate parent's anniversary, as well as family wedding in the area. What a wonderful location and home!!! The owners are great, love their home and love sharing it with others. We had a relaxing time with adult children, with plenty of space for private conversations as well as for all of us together in the same room. The home is well stocked, including coffee and eggs: the furnishings are beautiful, plus decorated for Christmas, and very...
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

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

9.8 out of 10, Exceptional, (76)
"Great location. Nice play to stay."
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!

Broadhead Mountain Retreat | 2 Bedroom, 2 Bath

9.6 out of 10, Exceptional, (46)
"Such a unique, amazing stay. We are so happy we found this property for an early Thanksgiving getaway in Charlottesville to visit our family. The kitchen was stocked with enough pots and pans and appliances that it was perfect for making a full Thanksgiving meal. We loved it!"
Broadhead Mountain Retreat | 2 Bedroom, 2 Bath

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (70)
"Excellent location for our visit to Monticello and Charlottesville. The cottage was very clean and comfortable and the foothills scenery - plus wildlife - was beautiful. The weather was a bit cool for the hot tub but the farm and pastures were exactly the respite for which we were planning. Our host, Steve, called to check in and offer recommendations. Great visit to Monticello, Jefferson Vineyards, the Highlands, Boars Head and Charlottesville."
1802 cottage once part of Monticello and owned by Thomas Jefferson

Ridgeview Cottage: Mtn Views and Fall Foliage!

9.2 out of 10, Wonderful, (10)
"It’s perfect for a family of 4 or two couples. The pool is amazing, the ambiance, the lighting just perfect for pictures. Also, the cottage equipped with everything needed. We were able to get instacart & DoorDash to deliver. Good time in deed and plan on going back next year for sure. "
The price is AU$599
includes taxes & fees
5 Jan - 6 Jan 2025
Ridgeview Cottage: Mtn Views and Fall Foliage!

GreenLeaf |3 bed, 2 Bath in Rugby Hills - Great central location UVA and Downtown Cville!

9.6 out of 10, Exceptional, (7)
"Three moms looking to get away for a weekend and enjoy uninterrupted conversations and tons of laughter. House was adorable and we will be dreaming of the patio for some time to come. Perfect walking distance to mall area and morning breakfast locations. Quiet and cozy...just what we needed."
GreenLeaf |3 bed, 2 Bath in Rugby Hills - Great central location UVA and Downtown Cville!

Massanutten's Woodstone Meadows by Tripforth

4.0 star property
9.0 out of 10, Wonderful, (191)
"We love the location - close to Shenandoah National Park and fun things to do in Harrisonburg. Local wine, beer, and cider tastings are fun too!"
Massanutten's Woodstone Meadows by Tripforth

Massanutten Resort by Tripforth

3.0 star property
7.8 out of 10, Good, (145)
"Beautiful area! Check in took us over a hour. Not enough details on the rental information "
Massanutten Resort by Tripforth

The Summit at Massanutten Resort by Tripforth

3.5 star property
9.2 out of 10, Wonderful, (49)
"Will stay again "
The Summit at Massanutten Resort by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4.0 star property
7.6 out of 10, Good, (126)
"Went to a resort during “off season” less stuff to do."
Massanuttens Shenandoah Villas by Tripforth

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

9.0 out of 10, Wonderful, (256)
"My wife Teresa and I have been staying here for 11 years now. Every year for the last eleven years we have stayed the last week of Oct. The view is incredible. It never gets old. Something else that is very important to my wife and I is that the foyer door is only about 15 feet from the parking lot and its a flat walkway. Also, once in the foyer, its literally 2 steps to the stairs which are only 9 stairs. Most condos at Wintergreen are a hike just getting to the front door of the unit. Not...
The price is AU$392
includes taxes & fees
5 Jan - 6 Jan 2025
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

9.6 out of 10, Exceptional, (285)
"We really enjoyed our stay Host Scott was very informative and has very clear information. The house is very family friendly. We loved being able to use the fireplace. The hot tub was spectacular my wife usually never likes Hot Tubs but used this one twice. Kids loved the indoor basketball hoops and pac-man . My wife grew up with pac-man so she really loved it. We booked the house for my BD and we had some great memories. We were very lucky ski resort was open so the kids loved that. Thank so...
The price is AU$621
includes taxes & fees
13 Jan - 14 Jan 2025
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Massanutten's Regal Vistas by Tripforth

3.5 star property
8.6 out of 10, Excellent, (50)
"one negative point here is - there are lot many cockroaches. You must do serious pesticide treatment for the entire building to get rid of cockroaches from kitchen to bath-tub to bed."
Massanutten's Regal Vistas by Tripforth

Cottage near Shenandoah NP Old Rag and White Oak Canyon

9.8 out of 10, Exceptional, (58)
"Super nice cabin. It was nicely decorated and the bed was super comfortable!"
Cottage near Shenandoah NP Old Rag and White Oak Canyon

Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging

10.0 out of 10, Exceptional, (191)
"Everything about the property was planned and built with top quality. It was easy to communicate with Terry who was very friendly. We have never stayed at a property with such access to privacy yet many on-site activities. We loved it. Well worth the drive!"
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging

Secluded Stanardsville Cabin w/ 10 Acres & Hot Tub

10.0 out of 10, Exceptional, (80)
"Very impressed by the quiet and solitude of the location. Because of almost zero light pollution, we were able to go outside at night and enjoy the stars on an absolutely clear evening. Thank you for the opportunity to stay in your warm and inviting cabin. "
Secluded Stanardsville Cabin w/ 10 Acres & Hot Tub

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (298)
"This house was so beautiful! It was the best stocked vrbo we've stayed in with everything for the kitchen, bath, games and even a few dog toys! The hosts have thought of every little detail. Highly recommend. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Lovely Wooded Cabin with Numerous Trails On-Site!

10.0 out of 10, Exceptional, (64)
"Our 2nd time staying here. Beautiful, quiet and cozy place. Plenty to explore, horses to meet, wonderful communication with owner. The perfect spot to get away from the everyday hectic life. We will be back. "
Lovely Wooded Cabin with Numerous Trails On-Site!

Hot Tub, Scenic Views, Pet Friendly!

9.8 out of 10, Exceptional, (183)
"The house was absolutely perfect and beautiful for our small very intimate non traditional wedding."
Hot Tub, Scenic Views, Pet Friendly!
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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Other types of properties in Charlottesville you may be interested in

English Inn of Charlottesville

3.0 star property
9.2 out of 10, Wonderful, (1977)
"BEST BREAKFAST! ESP. THE POTATOES! VERY CLEAN! STAFF ARE LOVELY TOO!"
The price is AU$173
includes taxes & fees
23 Dec - 24 Dec
English Inn of Charlottesville

Omni Charlottesville Hotel

4.0 star property
8.8 out of 10, Excellent, (1006)
"I enjoyed the location, especially due to seeing a concert at the Paramount. The hotel comes with beautiful views. However, it’s very noisy even when not crowded. And the food was just so so. But the room was nice."
The price is AU$291
includes taxes & fees
5 Jan - 6 Jan 2025
Omni Charlottesville Hotel

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3.0 star property
9.0 out of 10, Wonderful, (1008)
"Nice for a night on the road. Beds are good, and breakfast was fine."
The price is AU$154
includes taxes & fees
2 Jan - 3 Jan 2025
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
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.

Frequently asked questions

Can I find holiday rentals in Charlottesville?

Yes, there are holiday rentals in Charlottesville close to Charlottesville Ice Park, 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'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.

How many holiday rentals will I find in Charlottesville?

With 168 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 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.