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Holiday Homes in Charlottesville

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113 rentals in Charlottesville.
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H'Owl at the Moon Farm and Cabin, holiday rental in Charlottesville
H'Owl at the Moon Farm and Cabin, holiday rental in Charlottesville
H'Owl at the Moon Farm and Cabin, holiday rental in Charlottesville

H'Owl at the Moon Farm and Cabin

Cabin Holiday Rental
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Retreat on 10 Acres Minutes from Monticello, Wineries & Charlottesville!, holiday rental in Charlottesville
Private Retreat on 10 Acres Minutes from Monticello, Wineries & Charlottesville!, holiday rental in Charlottesville
Private Retreat on 10 Acres Minutes from Monticello, Wineries & Charlottesville!, holiday rental in Charlottesville

Private Retreat on 10 Acres Minutes from Monticello, Wineries & Charlottesville!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Stay Minutes from ~UVA~, Yet Feel Like You're in the Country—On 5 Ac. w/ Pond, holiday rental in Charlottesville
Stay Minutes from ~UVA~, Yet Feel Like You're in the Country—On 5 Ac. w/ Pond, holiday rental in Charlottesville
Stay Minutes from ~UVA~, Yet Feel Like You're in the Country—On 5 Ac. w/ Pond, holiday rental in Charlottesville

Stay Minutes from ~UVA~, Yet Feel Like You're in the Country—On 5 Ac. w/ Pond

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Renovated Belmont Bungalow, Walk to Restaurants, DT, UVA, Attractions, holiday rental in Charlottesville
Renovated Belmont Bungalow, Walk to Restaurants, DT, UVA, Attractions, holiday rental in Charlottesville
Renovated Belmont Bungalow, Walk to Restaurants, DT, UVA, Attractions, holiday rental in Charlottesville

Renovated Belmont Bungalow, Walk to Restaurants, DT, UVA, Attractions

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Secluded Escape for Family & Friends ~ Charlottesville ~, holiday rental in Charlottesville
Secluded Escape for Family & Friends ~ Charlottesville ~, holiday rental in Charlottesville
Secluded Escape for Family & Friends ~ Charlottesville ~, holiday rental in Charlottesville

Secluded Escape for Family & Friends ~ Charlottesville ~

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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The Recycled House - Walk Downtown, holiday rental in Charlottesville
The Recycled House - Walk Downtown, holiday rental in Charlottesville
The Recycled House - Walk Downtown, holiday rental in Charlottesville

The Recycled House - Walk Downtown

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Cottage at Sunnybank B&B, holiday rental in Charlottesville
The Cottage at Sunnybank B&B, holiday rental in Charlottesville
The Cottage at Sunnybank B&B, holiday rental in Charlottesville

The Cottage at Sunnybank B&B

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quaint and Cozy, 2 Bed, I Bath, Full Kitchen Cottage with Off Street Parking, holiday rental in Charlottesville
Quaint and Cozy, 2 Bed, I Bath, Full Kitchen Cottage with Off Street Parking, holiday rental in Charlottesville
Quaint and Cozy, 2 Bed, I Bath, Full Kitchen Cottage with Off Street Parking, holiday rental in Charlottesville

Quaint and Cozy, 2 Bed, I Bath, Full Kitchen Cottage with Off Street Parking

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Comfortable Charlottesville Town House, holiday rental in Charlottesville
Comfortable Charlottesville Town House, holiday rental in Charlottesville
Comfortable Charlottesville Town House, holiday rental in Charlottesville

Comfortable Charlottesville Town House

Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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C'ville Country Retreat for UVa Events~Wine Tours~Family/Friends Reunions, holiday rental in Charlottesville
C'ville Country Retreat for UVa Events~Wine Tours~Family/Friends Reunions, holiday rental in Charlottesville
C'ville Country Retreat for UVa Events~Wine Tours~Family/Friends Reunions, holiday rental in Charlottesville

C'ville Country Retreat for UVa Events~Wine Tours~Family/Friends Reunions

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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Beautiful Home - Great Location, minutes from Downtown, University of Virginia, holiday rental in Charlottesville
Beautiful Home - Great Location, minutes from Downtown, University of Virginia, holiday rental in Charlottesville
Beautiful Home - Great Location, minutes from Downtown, University of Virginia, holiday rental in Charlottesville

Beautiful Home - Great Location, minutes from Downtown, University of Virginia

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Dowtown Mall / Best Location in C-Ville - Rare House just off Main Street, holiday rental in Charlottesville
Dowtown Mall / Best Location in C-Ville - Rare House just off Main Street, holiday rental in Charlottesville
Dowtown Mall / Best Location in C-Ville - Rare House just off Main Street, holiday rental in Charlottesville

Dowtown Mall / Best Location in C-Ville - Rare House just off Main Street

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Renew*Coniferidge ... Located in a beautiful wooded setting., holiday rental in Charlottesville
Renew*Coniferidge ... Located in a beautiful wooded setting., holiday rental in Charlottesville
Renew*Coniferidge ... Located in a beautiful wooded setting., holiday rental in Charlottesville

Renew*Coniferidge ... Located in a beautiful wooded setting.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Azalea Cottage - adorable cottage within one mile of the University of Virginia, holiday rental in Charlottesville
Azalea Cottage - adorable cottage within one mile of the University of Virginia, holiday rental in Charlottesville
Azalea Cottage - adorable cottage within one mile of the University of Virginia, holiday rental in Charlottesville

Azalea Cottage - adorable cottage within one mile of the University of Virginia

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Afton Cottage: UVA, Monticello, Hiking, Wineries, Breweries., holiday rental in Charlottesville
Afton Cottage: UVA, Monticello, Hiking, Wineries, Breweries., holiday rental in Charlottesville
Afton Cottage: UVA, Monticello, Hiking, Wineries, Breweries., holiday rental in Charlottesville

Afton Cottage: UVA, Monticello, Hiking, Wineries, Breweries.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Rugby Hills-Walk  to University Rotunda/Downtown, holiday rental in Charlottesville
Rugby Hills-Walk  to University Rotunda/Downtown, holiday rental in Charlottesville
Rugby Hills-Walk  to University Rotunda/Downtown, holiday rental in Charlottesville

Rugby Hills-Walk to University Rotunda/Downtown

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Pryor-Haynes House | Walk to Downtown Mall | Historic Stately Home with Pool Tab, holiday rental in Charlottesville
Pryor-Haynes House | Walk to Downtown Mall | Historic Stately Home with Pool Tab, holiday rental in Charlottesville
Pryor-Haynes House | Walk to Downtown Mall | Historic Stately Home with Pool Tab, holiday rental in Charlottesville

Pryor-Haynes House | Walk to Downtown Mall | Historic Stately Home with Pool Tab

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Braeside Annex | Comfort Close to Boars Head & UVA, holiday rental in Charlottesville
Braeside Annex | Comfort Close to Boars Head & UVA, holiday rental in Charlottesville
Braeside Annex | Comfort Close to Boars Head & UVA, holiday rental in Charlottesville

Braeside Annex | Comfort Close to Boars Head & UVA

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Cabell Cottage | Garth Rd area guest house just 7 miles to UVA w/ wood-burning f

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Located In Trendy downtown Belmont, Easy Walk To Downtown Mall,UVA. Pet friendly, holiday rental in Charlottesville
Located In Trendy downtown Belmont, Easy Walk To Downtown Mall,UVA. Pet friendly, holiday rental in Charlottesville
Located In Trendy downtown Belmont, Easy Walk To Downtown Mall,UVA. Pet friendly, holiday rental in Charlottesville

Located In Trendy downtown Belmont, Easy Walk To Downtown Mall,UVA. Pet friendly

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Experience CHARLOTTESVILLE with charm❣️, holiday rental in Charlottesville
Experience CHARLOTTESVILLE with charm❣️, holiday rental in Charlottesville
Experience CHARLOTTESVILLE with charm❣️, holiday rental in Charlottesville

Experience CHARLOTTESVILLE with charm❣️

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Ingleridge Annex | 2-bed historic home just 3 miles to UVA up scenic Garth Rd, holiday rental in Charlottesville
Ingleridge Annex | 2-bed historic home just 3 miles to UVA up scenic Garth Rd, holiday rental in Charlottesville
Ingleridge Annex | 2-bed historic home just 3 miles to UVA up scenic Garth Rd, holiday rental in Charlottesville

Ingleridge Annex | 2-bed historic home just 3 miles to UVA up scenic Garth Rd

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Honey House--Newly renovated loft-style guesthouse near UVA/Downtown, holiday rental in Charlottesville
Honey House--Newly renovated loft-style guesthouse near UVA/Downtown, holiday rental in Charlottesville
Honey House--Newly renovated loft-style guesthouse near UVA/Downtown, holiday rental in Charlottesville

Honey House--Newly renovated loft-style guesthouse near UVA/Downtown

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Stadium Cottage | Beautiful Home Steps Away From Scott's Stadium/UVA Grounds, holiday rental in Charlottesville
Stadium Cottage | Beautiful Home Steps Away From Scott's Stadium/UVA Grounds, holiday rental in Charlottesville
Stadium Cottage | Beautiful Home Steps Away From Scott's Stadium/UVA Grounds, holiday rental in Charlottesville

Stadium Cottage | Beautiful Home Steps Away From Scott's Stadium/UVA Grounds

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Westview Haus- walking distance to UVA, Scott Stadium, JPJ Arena, dining/shops, holiday rental in Charlottesville
Westview Haus- walking distance to UVA, Scott Stadium, JPJ Arena, dining/shops, holiday rental in Charlottesville
Westview Haus- walking distance to UVA, Scott Stadium, JPJ Arena, dining/shops, holiday rental in Charlottesville

Westview Haus- walking distance to UVA, Scott Stadium, JPJ Arena, dining/shops

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Premium Downtown Charlottesville 1900's Renovated Abode in Belmont Neighborhood, holiday rental in Charlottesville
Premium Downtown Charlottesville 1900's Renovated Abode in Belmont Neighborhood, holiday rental in Charlottesville
Premium Downtown Charlottesville 1900's Renovated Abode in Belmont Neighborhood, holiday rental in Charlottesville

Premium Downtown Charlottesville 1900's Renovated Abode in Belmont Neighborhood

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cavalier Cove | Fantastic location, Walking distance to UVA, and free trolley st, holiday rental in Charlottesville
Cavalier Cove | Fantastic location, Walking distance to UVA, and free trolley st, holiday rental in Charlottesville
Cavalier Cove | Fantastic location, Walking distance to UVA, and free trolley st, holiday rental in Charlottesville

Cavalier Cove | Fantastic location, Walking distance to UVA, and free trolley st

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
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Corner House | Stylish Belmont Home, Walk to Downtown Mall

Corner House | Styli, holiday rental in Charlottesville
Corner House | Stylish Belmont Home, Walk to Downtown Mall

Corner House | Styli, holiday rental in Charlottesville
Corner House | Stylish Belmont Home, Walk to Downtown Mall

Corner House | Styli, holiday rental in Charlottesville

Corner House | Stylish Belmont Home, Walk to Downtown Mall Corner House | Styli

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bright, Spacious Home Perfect for Groups (5 Beds), holiday rental in Charlottesville
Bright, Spacious Home Perfect for Groups (5 Beds), holiday rental in Charlottesville
Bright, Spacious Home Perfect for Groups (5 Beds), holiday rental in Charlottesville

Bright, Spacious Home Perfect for Groups (5 Beds)

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Stay at Knight's Gambit Vineyard, holiday rental in Charlottesville
Stay at Knight's Gambit Vineyard, holiday rental in Charlottesville
Stay at Knight's Gambit Vineyard, holiday rental in Charlottesville

Stay at Knight's Gambit Vineyard

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautifully Rustic Cabin just 10 minutes from UVA, with pool!, holiday rental in Charlottesville
Beautifully Rustic Cabin just 10 minutes from UVA, with pool!, holiday rental in Charlottesville
Beautifully Rustic Cabin just 10 minutes from UVA, with pool!, holiday rental in Charlottesville

Beautifully Rustic Cabin just 10 minutes from UVA, with pool!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Spacious Apartment at Ivy Farms near Barracks and central Charlottesville, holiday rental in Charlottesville
Spacious Apartment at Ivy Farms near Barracks and central Charlottesville, holiday rental in Charlottesville
Spacious Apartment at Ivy Farms near Barracks and central Charlottesville, holiday rental in Charlottesville

Spacious Apartment at Ivy Farms near Barracks and central Charlottesville

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!, holiday rental in Charlottesville
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!, holiday rental in Charlottesville
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!, holiday rental in Charlottesville

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Recycled House - Walk Downtown, holiday rental in Charlottesville
The Recycled House - Walk Downtown, holiday rental in Charlottesville
The Recycled House - Walk Downtown, holiday rental in Charlottesville

The Recycled House - Walk Downtown

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Payment Protection
Unique private space in downtown Charlottesville, holiday rental in Charlottesville
Unique private space in downtown Charlottesville, holiday rental in Charlottesville
Unique private space in downtown Charlottesville, holiday rental in Charlottesville

Unique private space in downtown Charlottesville

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Boutique Hotel Room above The Jefferson Theater on the Downtown Mall, holiday rental in Charlottesville
Boutique Hotel Room above The Jefferson Theater on the Downtown Mall, holiday rental in Charlottesville
Boutique Hotel Room above The Jefferson Theater on the Downtown Mall, holiday rental in Charlottesville

Boutique Hotel Room above The Jefferson Theater on the Downtown Mall

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Belmont Flat | Located in the popular Belmont neighborhood, just a stroll aw, holiday rental in Charlottesville
The Belmont Flat | Located in the popular Belmont neighborhood, just a stroll aw, holiday rental in Charlottesville
The Belmont Flat | Located in the popular Belmont neighborhood, just a stroll aw, holiday rental in Charlottesville

The Belmont Flat | Located in the popular Belmont neighborhood, just a stroll aw

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Blue Bungalow | Renovated 1890`s Farmhouse, close to UVA and Downtown.

Blue Bun, holiday rental in Charlottesville
Blue Bungalow | Renovated 1890`s Farmhouse, close to UVA and Downtown.

Blue Bun, holiday rental in Charlottesville
Blue Bungalow | Renovated 1890`s Farmhouse, close to UVA and Downtown.

Blue Bun, holiday rental in Charlottesville

Blue Bungalow | Renovated 1890`s Farmhouse, close to UVA and Downtown. Blue Bun

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Socially isolate - brand new tiny house close to UVA, holiday rental in Charlottesville
Socially isolate - brand new tiny house close to UVA, holiday rental in Charlottesville
Socially isolate - brand new tiny house close to UVA, holiday rental in Charlottesville

Socially isolate - brand new tiny house close to UVA

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Townsman Hotel | Secretariat Room, holiday rental in Charlottesville
Townsman Hotel | Secretariat Room, holiday rental in Charlottesville
Townsman Hotel | Secretariat Room, holiday rental in Charlottesville

Townsman Hotel | Secretariat Room

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Well Appointed Home For Your Family's Enjoyment In The Heart Of Charlottesville, holiday rental in Charlottesville
Well Appointed Home For Your Family's Enjoyment In The Heart Of Charlottesville, holiday rental in Charlottesville
Well Appointed Home For Your Family's Enjoyment In The Heart Of Charlottesville, holiday rental in Charlottesville

Well Appointed Home For Your Family's Enjoyment In The Heart Of Charlottesville

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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One mile from University of Virginia and UVA Medical Center, holiday rental in Charlottesville
One mile from University of Virginia and UVA Medical Center, holiday rental in Charlottesville
One mile from University of Virginia and UVA Medical Center, holiday rental in Charlottesville

One mile from University of Virginia and UVA Medical Center

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Cozy Suite on Historic Property - Explore Nearby Vineyards and Wineries, holiday rental in Charlottesville
Cozy Suite on Historic Property - Explore Nearby Vineyards and Wineries, holiday rental in Charlottesville
Cozy Suite on Historic Property - Explore Nearby Vineyards and Wineries, holiday rental in Charlottesville

Cozy Suite on Historic Property - Explore Nearby Vineyards and Wineries

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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NEW! Charming Charlottesville Apt w/ Outdoor Space, holiday rental in Charlottesville
NEW! Charming Charlottesville Apt w/ Outdoor Space, holiday rental in Charlottesville
NEW! Charming Charlottesville Apt w/ Outdoor Space, holiday rental in Charlottesville

NEW! Charming Charlottesville Apt w/ Outdoor Space

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Nest on Locust | Stylish Downtown Villa

Nest on Locust | Stylish Downtown Villa, holiday rental in Charlottesville
Nest on Locust | Stylish Downtown Villa

Nest on Locust | Stylish Downtown Villa, holiday rental in Charlottesville
Nest on Locust | Stylish Downtown Villa

Nest on Locust | Stylish Downtown Villa, holiday rental in Charlottesville

Nest on Locust | Stylish Downtown Villa Nest on Locust | Stylish Downtown Villa

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Newly Renovated Private Cottage near Wineries, holiday rental in Charlottesville
Newly Renovated Private Cottage near Wineries, holiday rental in Charlottesville
Newly Renovated Private Cottage near Wineries, holiday rental in Charlottesville

Newly Renovated Private Cottage near Wineries

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Doggone fun 3 bdr Home at UVA with a Free Breakfast!, holiday rental in Charlottesville
Doggone fun 3 bdr Home at UVA with a Free Breakfast!, holiday rental in Charlottesville
Doggone fun 3 bdr Home at UVA with a Free Breakfast!, holiday rental in Charlottesville

Doggone fun 3 bdr Home at UVA with a Free Breakfast!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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The Wood Company Loft | Fully renovated modern apartment overlooking the Downtow, holiday rental in Charlottesville
The Wood Company Loft | Fully renovated modern apartment overlooking the Downtow, holiday rental in Charlottesville
The Wood Company Loft | Fully renovated modern apartment overlooking the Downtow, holiday rental in Charlottesville

The Wood Company Loft | Fully renovated modern apartment overlooking the Downtow

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Graves Street Magnolia | Charming classic Belmont home located within a stone's, holiday rental in Charlottesville
Graves Street Magnolia | Charming classic Belmont home located within a stone's, holiday rental in Charlottesville
Graves Street Magnolia | Charming classic Belmont home located within a stone's, holiday rental in Charlottesville

Graves Street Magnolia | Charming classic Belmont home located within a stone's

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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The Redwood House | Walk to UVA and Scott Stadium

The Redwood House | Walk to U, holiday rental in Charlottesville
The Redwood House | Walk to UVA and Scott Stadium

The Redwood House | Walk to U, holiday rental in Charlottesville
The Redwood House | Walk to UVA and Scott Stadium

The Redwood House | Walk to U, holiday rental in Charlottesville

The Redwood House | Walk to UVA and Scott Stadium The Redwood House | Walk to U

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Frequently Asked Questions about Charlottesville