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Charlottesville Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Charlottesville

Fridge, microwave, oven, stovetop
Ivy Rose Cottage nestled b/t Cville & Vineyards

Cabin in Charlottesville

10.0 out of 10, Exceptional, (65)
"Loved staying here!"
United States
Rebecca E.
The price is HK$1,393
HK$2,632 total
includes taxes & fees
30 Nov - 1 Dec
Ivy Rose Cottage nestled b/t Cville & Vineyards
Property grounds
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Holiday Home in Charlottesville

10.0 out of 10, Exceptional, (254)
"We can’t wait to get back! Our cups are full - thank you for everything!"
United States
Ann Miller W. M.
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Exterior
Unique Cypress cottage, close to Charlottesville with mountain views.

Cottage in Charlottesville

10.0 out of 10, Exceptional, (45)
"Lovely stay. Clean, comfortable, quaint, and roomy. Perfect location for our family!"
United States
kim E.
The price is HK$1,143
HK$2,205 total
includes taxes & fees
30 Nov - 1 Dec
Unique Cypress cottage, close to Charlottesville with mountain views.
Smart TV
Loveshack, a charming tiny house on a 5 acre farm

Cottage in Charlottesville

9.4 out of 10, Exceptional, (10)
"My wife and I had a great weekend getaway. Property was great. Close to restaurants and hiking. Great hosts."
United States
Zachary G.
Loveshack, a charming tiny house on a 5 acre farm
Exterior
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy

Cabin in Stanardsville

2.0 star property
9.6 out of 10, Exceptional, (50)
"Great cabin!! "
United States
Sami
The price is HK$721
HK$1,169 total
includes taxes & fees
3 Dec - 4 Dec
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
Indoor pool, outdoor pool
Massanutten Resort by Tripforth

Holiday Home in McGaheysville

3.0 star property
7.8 out of 10, Good, (158)
"Spacious facility, quiet/peaceful atmosphere "
United States
Lisa
Massanutten Resort by Tripforth
Exterior
Massanutten's Woodstone Meadows by Tripforth

Holiday Home in McGaheysville

4.0 star property
9.0 out of 10, Wonderful, (219)
"Nice and quiet place to stay over the weekend and food was great "
United States
Pablo
Massanutten's Woodstone Meadows by Tripforth
Aerial view
The Summit at Massanutten Resort by Tripforth

Holiday Home in McGaheysville

3.5 star property
9.0 out of 10, Wonderful, (67)
"Beautiful resort, clean & spacious condo. Lots of activities for the family to enjoy. I recommend staying away from the timeshare presentation they offer guest. "
United States
Shaunte'
The price is HK$4,151
HK$4,836 total
includes taxes & fees
28 Dec - 29 Dec
The Summit at Massanutten Resort by Tripforth
Exterior
Wow! What A View!

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (54)
"Very clean, very comfortable, easy to access - we honestly didn't want to leave."
United States
Josh W.
Wow! What A View!
Terrace/patio
Love Ridge Mountain Lodging

Cabin in Montebello

3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is HK$1,383
HK$2,020 total
includes taxes & fees
4 Dec - 5 Dec
Love Ridge Mountain Lodging
Property grounds
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (53)
"Great place to stay in Wintergreen!"
United States
Caroline w.
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall
Terrace/patio
New Build! Log Cabin with Hot Tub in Wintergreen

Cabin in Chestnut Springs

10.0 out of 10, Exceptional, (3)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
New Build! Log Cabin with Hot Tub in Wintergreen
Property grounds
The Cabin at the Lake

Cabin in Madison

9.8 out of 10, Exceptional, (42)
"Such a lovely and peaceful location. The proximity to Early Mountain Winery was perfect."
United States
Randy D.
The price is HK$1,225
HK$2,252 total
includes taxes & fees
30 Nov - 1 Dec
The Cabin at the Lake
Exterior
Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.

Chalet in Elkton

10.0 out of 10, Exceptional, (31)
"Amazing location right up against the national park land. Very nicely furnished and well appointed in every way!"
United States
Chris W.
Cozy Chalet bordering Shenandoah Park near Massanutten Resort and Skyline Drive.
Interior detail
Afton Mountain Vineyards

Cabin in Afton

2.5 star property
10.0 out of 10, Exceptional, (1)
"Amazing little cottage with everything you need. Loved the back porch and listening to music from the winery and enjoying the view. Good news, did not hear the music inside. "
United States
Kristin
The price is HK$2,722
HK$3,057 total
includes taxes & fees
2 Dec - 3 Dec
Afton Mountain Vineyards
Exterior
Beautiful Big Resort Home,Views, Pool table, Ping Pong, Air Hockey, Foosball

Holiday Home in Massanutten

10.0 out of 10, Exceptional, (395)
"The house was clean and had everthing we needed. The game room qas awesome. "
United States
John S.
Beautiful Big Resort Home,Views, Pool table, Ping Pong, Air Hockey, Foosball
Property grounds
Cub Cabin on Massanutten Resort- Fully Renovated Log Cabin- Hot Tub & Fire Pit

Cabin in Massanutten

10.0 out of 10, Exceptional, (96)
"Absolutely beautiful cabin! The beds were extremely comfortable. Cabin was clean and kids loved the chocolates and chips. Will definitely stay again in the future! This is an A plus cabin! "
United States
Mike Stef M.
Cub Cabin on Massanutten Resort- Fully Renovated Log Cabin- Hot Tub & Fire Pit
Miscellaneous
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Condo in Wintergreen

10.0 out of 10, Exceptional, (251)
"The condo was absolutely lovely! We had great time in Wintergreen and will definitely go back. "
United States
Dawn C.
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!
Smart TV
Massanutten Chalet

Chalet in McGaheysville

10.0 out of 10, Exceptional, (44)
"Nice property. Clean, responsive owner, appreciated the little extras. We had 6 people staying and there was plenty of room. Would stay here again. "
United States
Jan
The price is HK$1,036
HK$2,738 total
includes taxes & fees
30 Nov - 1 Dec
Massanutten Chalet
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Condo in Roseland

9.0 out of 10, Wonderful, (300)
"Great view!!"
United States
Suzanne W.
The price is HK$770
HK$1,843 total
includes taxes & fees
2 Dec - 3 Dec
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
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

English Inn of Charlottesville

English Inn of Charlottesville

10/10 Excellent
"Clean room , excellent staff"
Bruce 2-night trip
Posted 1 day ago
English Inn of Charlottesville

Find out more about Charlottesville

Search for holiday rentals in Charlottesville on Expedia! You can easily find your home rentals, villas, holiday apartments in Charlottesville using one of the methods below:

  • View our selection of featured holiday rentals in Charlottesville
  • Use the map to find apartments and other holiday homes in the Charlottesville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Charlottesville while they last

Look no further and take a look at our great range of rental properties in Charlottesville!

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'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 181 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.