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Vacation Rentals near James Monroe's Highland

2050 James Monroe Pkwy, Charlottesville, Virginia 22902-7546
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    Travelers to Charlottesville are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    All 225 Rentals in Charlottesville
    Charlottesville, 1830's Row-house 1 Block from Downtown Pedestrian Mall1 / 37
    (2)Very good
    3.9 miles from James Monroe's Highland
    4 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    Park St Flat | 2 Bed, 1 Bath1 / 9
    (27)Very good
    4.2 miles from James Monroe's Highland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Old Met #201 | Downtown Mall at 1st & Main1 / 17
    (11)Very good
    4.1 miles from James Monroe's Highland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Arbor House basement for the VA Film Fest in Nov.1 / 16
    3.5 miles from James Monroe's Highland
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Charlottesville, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Avon House in Historic Downtown near the mall, UVA, restaurants & free trolley1 / 21
    3.5 miles from James Monroe's Highland
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Avon House is a beautiful, 1925 corner brick house with plenty of available parking. The house has been renovated throughout with new HVAC system, electrics and plumbing! The upstairs bathroom has a clawfoot tub and an enclosed steam shower spa with music! All bedrooms are spacious. Enjoy the 46'...
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    Charlottesville, Virginia
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Quiet Garden Suite Near UVA, Private Entrance, Private Guest Parking, WiFi1 / 24
    (2)Excellent
    4.0 miles from James Monroe's Highland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charlottesville, Virginia
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Townsman Hotel: Meriwether | 0 Bed, 1 Bath1 / 9
    (6)Very good
    3.7 miles from James Monroe's Highland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charlottesville, Virginia
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Old Met #306 | 2 Bed, 2 Bath1 / 25
    (12)Very good
    4.0 miles from James Monroe's Highland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Charlottesville, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Walk To UVA: Gorgeous European $2M Rugby Road -Old World 2016 built !!1 / 30
    (4)Excellent
    5.2 miles from James Monroe's Highland
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Charlottesville, Virginia
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Nest on Locust | 2 Bed, 2 Bath1 / 17
    (10)Excellent
    4.3 miles from James Monroe's Highland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Quaint and Cozy, 2 Bed, I Bath, Full Kitchen Cottage with Off Street Parking1 / 15
    (83)Excellent
    3.3 miles from James Monroe's Highland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    4 BR Cozy Home near UVA, Downtown & Wineries1 / 30
    (8)Very good
    3.7 miles from James Monroe's Highland
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Charlottesville, Virginia
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    Luxury 5-Bed Charlottesville Home Close to Farmington Country Club1 / 21
    (3)Excellent
    7.2 miles from James Monroe's Highland
    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    Charlottesville, Virginia
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 10
    Located In Trendy downtown Belmont, Easy Walk To Downtown Mall,UVA. Pet friendly1 / 10
    (81)Excellent
    3.5 miles from James Monroe's Highland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Skiing: Property Is In A Ski Resort
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Doggone Fun 3bdr UVA Home w/ free breakfast.1 / 23
    (5)Very good
    5.0 miles from James Monroe's Highland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Charlottesville, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    The Belmont Flat | 0 Bed, 1 Bath1 / 16
    (46)Very good
    3.4 miles from James Monroe's Highland
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    Charlottesville, Virginia
    Condo/Apartment - 1 Bathroom, Sleeps 3
    C'ville Country Retreat for UVa Events~Wine Tours~Family/Friends Reunions1 / 24
    (72)Excellent
    9.4 miles from James Monroe's Highland
    5 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    Charlottesville, Virginia
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 20
    Broadhead Mountain Retreat | 3 Bed, 2 Bath1 / 25
    7.8 miles from James Monroe's Highland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Charlottesville, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Downtown Carriage House | Located a short walk from the historic downtown mall1 / 16
    (16)Very good
    3.8 miles from James Monroe's Highland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Pryor-Haynes House | 4 Bed, 4.5 Bath1 / 30
    (69)Excellent
    3.6 miles from James Monroe's Highland
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Charlottesville, Virginia
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Corner House | Stylish Belmont Home, Walk to Downtown Mall1 / 23
    (36)Very good
    3.6 miles from James Monroe's Highland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Charlottesville, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Comfortable Charlottesville Town House1 / 30
    (87)Excellent
    2.9 miles from James Monroe's Highland
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 4 Bathrooms, Sleeps 6
    Doggone fun 3 bdr Home at UVA with a Free Breakfast!1 / 22
    (9)Excellent
    5.0 miles from James Monroe's Highland
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Charlottesville, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Cabell Cottage | 2 Bed, 1.5 Bath1 / 30
    (24)Excellent
    8.8 miles from James Monroe's Highland
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    C'ville Country Home for Family & Friends, Close to UVA and Wineries/Breweries1 / 27
    (8)Excellent
    11.2 miles from James Monroe's Highland
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Charlottesville, Virginia
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedroom, 1 Bath, Full Kitchen with Laundry,1 / 14
    (10)Excellent
    4.3 miles from James Monroe's Highland
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Charlottesville, Virginia
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Old Met #202 | Corner View Overlooking Downtown Mall1 / 16
    3.8 miles from James Monroe's Highland
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Charlottesville, Virginia
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Townsman Hotel: Faulkner | 0 Bed, 1 Bath1 / 11
    (39)Very good
    4.1 miles from James Monroe's Highland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charlottesville, Virginia
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Renew*Coniferidge ... Located in a beautiful wooded setting.1 / 27
    (50)Excellent
    9.8 miles from James Monroe's Highland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charlottesville, Virginia
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive1 / 28
    4.1 miles from James Monroe's Highland
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Four blocks to UVA, Scott Stadium. Two blocks to restaurants, free trolley stop.1 / 27
    (1)Excellent
    4.7 miles from James Monroe's Highland
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Charlottesville, Virginia
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Meriwether Springs Vineyard Estate | Professionally Cleaned1 / 21
    (18)Excellent
    9.9 miles from James Monroe's Highland
    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Charlottesville, Virginia
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 14
    Quiet Comfy Cottage - Super Clean - Equipped for Comfort and Enjoyment!1 / 13
    (6)Excellent
    4.8 miles from James Monroe's Highland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Townsman Hotel: Secretariat | 0 Bed, 1 Bath1 / 9
    (15)Very good
    3.9 miles from James Monroe's Highland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charlottesville, Virginia
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Welcome to the Wonderfully Comfortable, Caboose at CVille Cottage1 / 19
    (1)Very good
    4.8 miles from James Monroe's Highland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Blue Bungalow | 4 Bed, 2 Bath1 / 18
    (30)Excellent
    4.2 miles from James Monroe's Highland
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Charlottesville, Virginia
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Azalea Cottage - adorable cottage within one mile of the University of Virginia1 / 23
    (98)Excellent
    4.9 miles from James Monroe's Highland
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Belmont Carriage House1 / 30
    (7)Very good
    2.8 miles from James Monroe's Highland
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Charlottesville, Virginia
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Family-Friendly 1830s Cville Row House Near Downtown Mall, UVA, & Monticello1 / 30
    (17)Very good
    3.9 miles from James Monroe's Highland
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Charlottesville, Virginia
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
    Newly Renovated White Brick Ranch-Minutes to UVA1 / 23
    5.8 miles from James Monroe's Highland
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Charlottesville, Virginia
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Boutique Room steps from Downtown Mall | Rose Jean - Room #51 / 24
    3.9 miles from James Monroe's Highland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charlottesville, Virginia
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Cottage on quiet farm close to town and wineries1 / 30
    2.8 miles from James Monroe's Highland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charlottesville, Virginia
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Boutique Hotel Suite above the Jefferson Theater on the Downtown Mall1 / 8
    (27)Very good
    3.8 miles from James Monroe's Highland
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Charlottesville, Virginia
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    ★ New 3 Bed/4 Bath | 10 min to UVA/Hospital/Wineries/Downtown Mall1 / 30
    4.2 miles from James Monroe's Highland
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Charlottesville, Virginia
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Charming Charlottesville Cottage1 / 28
    (12)Excellent
    5.6 miles from James Monroe's Highland
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    • Wi-Fi
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    • Skiing: Property Is In A Ski Resort
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    Location Information
    Charlottesville, Virginia
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 1
    Braeside Annex | Comfort Close to Boars Head & UVA1 / 22
    (27)Excellent
    8.6 miles from James Monroe's Highland
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    • Internet Access
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    Location Information
    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 3
    Blue Mountain Haven:: 5 BR Hilltop Country Retreat1 / 30
    (7)Very good
    11.3 miles from James Monroe's Highland
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Location Information
    Charlottesville, Virginia
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Chic Sun Bedroom & private bath in Baltimore md1 / 9
    4.1 miles from James Monroe's Highland
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    • Grill
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    Location Information
    Charlottesville, Virginia
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 1
    Stadium Cottage | Beautiful Home Steps Away From Scott's Stadium/UVA Grounds1 / 30
    4.8 miles from James Monroe's Highland
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Charlottesville, Virginia
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Treehouse in Charlottesville Downtown1 / 14
    3.6 miles from James Monroe's Highland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Grill
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    • Waterfront
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    Location Information
    Charlottesville, Virginia
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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