Holiday homes in Charlottesville
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Top-rated holiday homes in Charlottesville
Guests agree: These condos are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Charlottesville condo rentals
Weekly condo rentals
Condo in Wintergreen Resort
4.9 out of 5 average rating, 105 reviewsPanoramic Peak: Wintergreen Condo with Views
17 – 24 July
Condo in Wintergreen Resort
4.89 out of 5 average rating, 126 reviewsCondo - King Master Suite - Wintergreen Resort
8 – 15 Sept
Condo in Wintergreen Resort
4.99 out of 5 average rating, 141 reviews3 BR 3 BA, 2 story condo in Highlands
6 – 13 Jan
Condo in Wintergreen Resort
4.98 out of 5 average rating, 120 reviewsSlope side+Panoramic Mountain Views!
8 – 15 Sept
Condo in Wintergreen Resort
4.88 out of 5 average rating, 144 reviewsWander Lodge: Golf, Spa, Wine, or just a getaway
21 – 28 Feb
Condo in Wintergreen Resort
4.91 out of 5 average rating, 145 reviewsGorgeous Wintergreen Condo – 2-min to Slopes
15 – 22 Aug
Condo in Wintergreen Resort
4.94 out of 5 average rating, 106 reviewsCozy 2BR+4 min to slopes+hike+golf course view!
21 – 26 July
Condo in Wintergreen Resort
5.0 out of 5 average rating, 70 reviews1 bedroom condo close to hiking breweries & resort
3 – 10 Aug
Pet-friendly condo rentals
Condo in Wintergreen Resort
4.96 out of 5 average rating, 105 reviewsAll-Season 2bd/2ba next to Spa view of Golf Course
9 – 16 Nov
Condo in Wintergreen Resort
4.96 out of 5 average rating, 235 reviewsFive Minute Walk to Everything!
14 – 21 Jan
Condo in Wintergreen Resort
4.89 out of 5 average rating, 107 reviews1720 High Ridge at Wintergreen Resort
11 – 18 June
Condo in Wintergreen Resort
4.96 out of 5 average rating, 155 reviewsSki-in/Ski-out Wintergreen Highlands Condo -Views!
20 – 27 Sept
Condo in Roseland
4.94 out of 5 average rating, 33 reviewsNature’s Haven 1 Bedroom Condo Wintergreen Resort
19 – 26 Sept
Condo in Charlottesville
4.88 out of 5 average rating, 34 reviewsThe Townie 3 BD/2BA Historic Downtown Building
18 – 25 June
Condo in Charlottesville
4.96 out of 5 average rating, 24 reviewsLovely 2 bed 2 bathroom condo close to UVA
30 May – 4 June
Condo in Wintergreen Resort
4.92 out of 5 average rating, 83 reviewsBlue Ridge Retreat: Your Cozy Mountain Getaway
26 June – 3 July
Condo rentals with a pool
Condo in Wintergreen Resort
5.0 out of 5 average rating, 45 reviewsCozy Laurelwood condo-walk to slopes & restaurants
27 May – 3 June
Condo in Charlottesville
4.96 out of 5 average rating, 77 reviewsComfy Condo*Near DT/UVA/Wineries
12 – 19 May
Condo in Wintergreen Resort
4.97 out of 5 average rating, 96 reviews2 bdrm/2 full bath Best Views of Blue Ridge Mtns.
17 – 24 Nov
Condo in Wintergreen Resort
4.84 out of 5 average rating, 55 reviewsMajestic Mountain View’s from The Cliffs
3 – 10 June
Condo in Wintergreen Resort
4.84 out of 5 average rating, 63 reviewsIncredible mountain views from Peak-A-Bear Den
2 – 9 June
Condo in Roseland
4.93 out of 5 average rating, 74 reviewsCondo in Wintergreen Resort
1 – 8 Jan
Condo in Wintergreen Resort
4.88 out of 5 average rating, 34 reviewsWintergreen! Dog friendly, cozy and comfortable
27 Mar – 3 Apr
Condo in Nelson County
4.94 out of 5 average rating, 31 reviewsMountain View Wintergreen Condo - Sleeps up to 4
4 – 11 Nov
Quick stats about condo rentals in Charlottesville
Total rentals
30 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.2K reviews
Nightly prices starting at
$76 AUD before taxes and fees
Destinations to explore
- Richmond Accommodation & holiday rentals
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