Charlottesville Holiday Rentals

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Holiday Rentals in Charlottesville

Exterior
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
10.0 out of 10, Exceptional, (220)
"Bill and Cynthia are such amazing hosts and the property inside and out exemplifies it. What a great place to stay for some serious rural R&R! The property was very clean. They have thought of everything one would need for a delightful get away. If you forgot anything, just ask and they are sure to help one way or another. The Fresh eggs, courtesy of their chickens, were a treat and the farm animals are such fun…esp Posy, Zoey and Hemingway. We hope to return soon for a longer retreat! Thank you...
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Interior
Ivy Rose Cottage nestled b/t Cville & Vineyards
10.0 out of 10, Exceptional, (12)
"Very unique and quaint house. Property manager was so kind and helpful. Highly recommend."
The price is HK$1,640
per night
16 May - 17 May
Ivy Rose Cottage nestled b/t Cville & Vineyards
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, (271)
"Fantastic!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
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Property grounds
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
10.0 out of 10, Exceptional, (24)
"We absolutely loved our stay. But yes we did have 3 older people in their 70s and the stairs were many but we were able to rearrange baths and other activities based on floor level."
The price is HK$1,172
per night
16 May - 17 May
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
Terrace/patio
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead
10.0 out of 10, Exceptional, (12)
"What a pleasant little cottage, centrally located to Harrisburg, Bridgewater, and Staunton with easy access to Shenandoah National Park and several area wineries and breweries. There’s a great porch and deck area to relax and unwind outside, with ample open grassy areas as well."
Charming cottage retreat by Shenandoah National Park and Madison Run Trailhead
Interior
Massanutten Chalet
10.0 out of 10, Exceptional, (19)
"Owner was so sweet! Extremely helpful, answered so quickly. Came with my friends to go snow tubing and we enjoyed every moment! The home is truly beautiful and everything was perfect. Thank you so much (:"
The price is HK$1,156
per night
16 May - 17 May
Massanutten Chalet
Exterior
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
10.0 out of 10, Exceptional, (18)
"Pete's place was a great getaway. Just a quick drive to some great hikes in Shenandoah National Park. The house was clean, comfortable and had everything we needed. Plan to visit again in the fall!"
The price is HK$1,250
per night
19 May - 20 May
Pete's Place: Forest retreat near wineries, Blue Ridge School, and Shenandoah NP
Private kitchen
Lovely Wooded Cabin with Numerous Trails On-Site!
10.0 out of 10, Exceptional, (50)
"My husband and I had a lovely stay at the cabin! It was perfect for our anniversary trip. Close enough to Shenandoah National park for hiking yet secluded for the perfect off-grid feel."
Lovely Wooded Cabin with Numerous Trails On-Site!
Fridge, microwave, oven, stovetop
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!
9.8 out of 10, Exceptional, (65)
"Very nice and roomy, very quiet, only issue was the 2 flights of stairs"
The price is HK$1,094
per night
4 Jun - 5 Jun
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!
Property grounds
Relax at 3100 feet and enjoy the peace and tranquility
9.8 out of 10, Exceptional, (59)
"The listing was accurate to what is presented. Very clean and easy to find with GPS. Close drive to National Park entrance. Gorgeous views."
Relax at 3100 feet and enjoy the peace and tranquility
Fridge, microwave, stovetop, coffee/tea maker
Secluded Stanardsville Cabin w/ 10 Acres & Hot Tub
9.8 out of 10, Exceptional, (64)
"Cute cabin with everything you could need for a stay away with additional extras. Secluded location with relaxing river sounds"
Secluded Stanardsville Cabin w/ 10 Acres & Hot Tub
Property grounds
Cottage near Shenandoah NP Old Rag and White Oak Canyon
9.8 out of 10, Exceptional, (39)
"If you are looking for peace and quiet in a location near tons of hiking, wineries, breweries, and farms, stay here! Jen was a perfect host and the cottage is gorgeous. All of the appliances are new, the house itself is out of a magazine, and the bed is super comfortable. We loved that there is a washer and dryer, a perfect porch, a fire pit, games, books, tv, everything. We can't wait to visit again!"
Cottage near Shenandoah NP Old Rag and White Oak Canyon
Exterior
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
9.8 out of 10, Exceptional, (55)
"We had a lovely stay. The area was gorgeous and the house was comfortable and perfect for our family of 5."
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
Outdoor pool, a heated pool
1802 cottage once part of Monticello and owned by Thomas Jefferson
9.6 out of 10, Exceptional, (58)
"I had a great stay!"
1802 cottage once part of Monticello and owned by Thomas Jefferson
Outdoor dining
Restored Vintage Airstream at Craft Brewery
9.6 out of 10, Exceptional, (8)
"Cute, wonderful place"
Restored Vintage Airstream at Craft Brewery
Property grounds
Splendid European-Style Chalet w/ Game Room and Newly Renovated Baths
9.6 out of 10, Exceptional, (108)
"My family had this house built when Massanutten first opened back in the early 70’s. Started the build in 1973 moved in 1974 and sold in 2004. It was a girls weekend to go to some of the wineries and breweries. The house has plenty of room for large groups and has a ping pong and pool tables. Great to be able to stay in the house once again and remember 30 years of wonderful memories my family had in the house. Would definitely recommend this house."
Splendid European-Style Chalet w/ Game Room and Newly Renovated Baths
TV
GreenLeaf |3 bed, 2 Bath in Rugby Hills - Great central location UVA and Downtown Cville!
9.4 out of 10, Exceptional, (3)
"House was comfortable and cozy, in a quiet, leafy neighborhood. Beds were super comfy, bedding was very nice. Well appointed kitchen and great outdoor dining area. A few glitches: 1. The Wi-Fi didn’t work. 2. There’s only one bathroom in the main house for three sleeping areas, which requires upstairs sleepers to descend a very steep staircase to use the bathroom. 3. The fourth single bed and second full bath are in the annex area, attached to the main house with a breezeway. Door to the...
GreenLeaf |3 bed, 2 Bath in Rugby Hills - Great central location UVA and Downtown Cville!
Exterior
Cozy modern cabin - the squirrel's nest
9.4 out of 10, Exceptional, (199)
"We had a great time staying at the Squirrel’s Nest. The location is secluded but still only 15 minutes away from Shenandoah. The cabin was warm & cozy and a perfect escape from everyday life. Hot tub was a plus!"
Cozy modern cabin - the squirrel's nest
Property grounds
Charming Farmhouse Cottage with Mountain Views
9.4 out of 10, Exceptional, (12)
"Great location in Orange County Va farm land very close to many attractions and with in reach to Charlottesville for a day trip via country road route 20 ( no traffic lights). The cottage is an outbuilding on the Bloomingdale Farm property that is surround by working farms. The view from the porch is peaceful and relaxing with the Blue Ridge off in the distance. The cottage is rustic with old wide plank pine floors that creek with every step. The first floor sitting room has a large working wood...
Charming Farmhouse Cottage with Mountain Views
Exterior
Autumn Ridge- Cozy cabin in the Blue Ridge Mountains with a bubbly hot tub!🗻
9.4 out of 10, Exceptional, (79)
"Our stay was amazing and everything we could have asked for, the cabin vibe was definitely there. The only thing we could think of that was bad about this place was the pictures on the ad could use a little updating (which is no big deal at all) other than that no problems and we plan to stay again sometime"
Autumn Ridge- Cozy cabin in the Blue Ridge Mountains with a bubbly hot tub!🗻
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See all available properties in Charlottesville
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.

Other types of properties in Charlottesville you may be interested in

Front of property
English Inn of Charlottesville
3.0 star property
9.0 out of 10, Wonderful, (1662)
"Nice place. Receptionist at check in not very friendly, but she got the job done"
The price is HK$837
per night
22 May - 23 May
English Inn of Charlottesville
Exterior
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Effortless check in/ checkout; and substantial breakfast . Essential comfortable room arrangements. "
The price is HK$911
per night
28 May - 29 May
Country Inn & Suites by Radisson, Charlottesville-UVA, VA
Terrace/patio
Omni Charlottesville Hotel
4.0 star property
8.8 out of 10, Excellent, (1003)
"Lovely hotel! We were in Charlottesville for a wedding and this was the perfect place to stay. The lobby area/conservatory is so beautiful. I also loved how the hotel is steps away from a charming promenade of streets and restaurants. I would absolutely stay here again if I find myself in Charlottesville for another occasion. "
The price is HK$1,461
per night
2 Jun - 3 Jun
Omni Charlottesville Hotel
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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Frequently asked questions

Can I find holiday rentals in Charlottesville?

Yes, there are holiday rentals in Charlottesville close to Virginia Discovery Museum, 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 entertainment choices 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 of 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 169 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.

Recent reviews of Charlottesville properties
Expedia verified reviews

Home2 Suites by Hilton Charlottesville Downtown

Home2 Suites by Hilton Charlottesville Downtown

5/5 Excellent
Fantastic hotel.
"Way better than expected. This place was better than my first apartment. I only stayed one night but I was super impressed with how efficiently the large space was used. The rooms were twice the size of another downtown hotel and cheaper too. "
A verified traveller stayed at Home2 Suites by Hilton Charlottesville Downtown
Posted 1 day ago
Home2 Suites by Hilton Charlottesville Downtown