
Places to stay near James Monroe's Highland
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Top-rated holiday rentals near James Monroe's Highland
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Private Apt in Historic C'ville Home (Garden Side)
This cozy, newly refurbished, 1 BR/1 Bath, apartment is attached to a historic Charlottesville home. With just a 10 min walk to the Downtown Mall and a short drive to the university hospital/campus, the location is nestled in the heart of C'ville. Special amenities include a Sleep Number bed, fast Wifi, a 50" Smart TV with access to Amazon Prime and Netflix, access to pool use during the summer, and Park Lane street parking. Hand crafted soapstone counters and farm sink, beautiful new tile work.

Belmont BnB ~ 2BR/1BA ~ Comfort & Convenience
Welcome to our well-appointed, centrally located 2 BR/1BA apartment! This cozy spot, with comfy queen beds, full kitchen, and cottage garden is a perfect homebase to relax in after a day of exploring. Set out on foot to: • Belmont Park (2 blocks) • Belmont Restaurants (15 min) • The Rivanna Trail (5 min) • The Downtown Mall (20 min) Short drives to Monticello (< 4 mi), grocery stores (1-2 mi), and UVA (2 mi). Your hosts are readily available in the above apartment should you need anything!

One Level Living at Shadwell Terrace
Set in the heart of Wine Enthusiast’s Wine Region of the Year, this newly renovated 2-bedroom, 800 sq/ft terrace level flat with separate entrance, is located in a private setting in the Keswick area. Close to Downtown Charlottesville, we are adjacent to Clifton Inn and Glenmore and minutes to Keswick Hall. After exploring many of Virginia’s wineries, breweries, and historical sites, kick your feet up between the trees in the hammock or share your adventures online with our high speed Wi-Fi.

Basic Belmont Apt w/ Air Hockey & near Downtown!
Perfect for a Cville getaway! Steps from downtown Belmont, under a mile from the Historic Downtown Mall, and 2 miles from UVA. Private access to this comfy studio apartment, perfect for a couple, small friend group, or family of 4. Queen bed plus pull-out couch & single futon. Full bath, kitchenette, TV, air hockey, & other games. Note: I live upstairs; there is no insulated ceiling so you may hear us when we're home. The HVAC is also in the apt, hence the budget price for this prime spot!

Unit 4 - Luxury King Suite with Private Balcony
Experience luxury and a unique journey through history at Sonsak - a newly renovated guesthouse in Albemarle County. Situated near the esteemed landmarks of Thomas Jefferson Parkway, Monticello, Ash Lawn and Michie Tavern, Ash, Sonsak is in a renowned area of historical significance. The property dates back to 1942 and has since been exquisitely renovated with lavish furnishings and modern amenities.Treat yourself to a stay at Sonsak and leave with lasting memories of comfort and beauty.

Honey B - Beautiful loft near UVA, Monticello
Best of both worlds! In beautiful nature but close to UVA, Monticello and downtown. Honey B (Honey House 2) has a lofty feel with the footprint of a small house. High ceilings and several skylights allow for light and privacy in the quiet neighborhood, Located on the southwest side of Charlottesville, just 7 minutes to Scott Stadium, UVA campus, and restaurants, 10 minutes to historic downtown mall, Thomas Jefferson’s Monticello and central to many major wineries and breweries.

Charming St. Charles
A beautifully renovated basement apartment in a family friendly neighborhood. Two blocks from our neighborhood park, with a connector to the Rivanna Trail. A 30 minute walk downtown, a bus stop one block away, & bike & scooter rentals make it much faster! Easy access to 250 bypass make Downtown & 29 North equally convenient destinations! Perfect for a couple with a young baby or toddler! Guests must acknowledge that footsteps and sound from our living area can be noisy!

The Belmont Loft ~ 15 min walk downtown, free park
Stay here! In the cutest house in Charlottesville's most beloved neighborhood. You'll be in the heart of Belmont, steps from some of the best restaurants in Cville, and a few blocks from the historic Downtown Mall - restaurants, shops, coffee, yoga, and music venues. 15-30 min ~ MANY popular wineries, breweries, and hiking in the Blue Ridge Mountains 10-15 min ~ Monticello 5 min ~ Monticello Trail 5-10 min ~ Rivanna River - trail and tubing 5-10 min ~ UVA

Cavalier Suite | Near UVA | Amenities | Parking
Small yet mighty. This carriage house is the perfect retreat for UVA games, special events, and those exploring Charlottesville. Conveniently located within walking distance to Scott Stadium, and a short distance to UVA, Downtown Charlottesville, and 5th Street Station Shopping Center. Hosts have 2 small, friendly dogs (Mac and Pippie) in the main house which may be seen in the patio entrance area. Guests have access to patio and grill.

Private Studio Basement Apt close to UVA
Located in the heart of Charlottesville! This house is close to UVA grounds, the downtown mall, and Belmont. You will be just a few minutes from great restaurants, shops, bars/breweries, and music venues. You’ll have your own private studio apartment in the basement of my house with a separate entrance. Enjoy the king-size bed, a private bathroom and living room with a stocked coffee bar. I would love to share my hometown with you!

Chic Casita – Private Retreat in Heart of Cville
Escape to our newly remodeled Chic Casita, a cozy one-bedroom basement apartment just minutes from UVA and downtown Charlottesville. Featuring great charm with modern touches, it offers a relaxing and comfortable space to unwind. Located in a quiet, safe neighborhood, you’ll enjoy peace and privacy while being close to top attractions, dining, and entertainment. Perfect for a relaxing vacation or getaway.

Luxury tiny house 3 min from UVA
La Casita is a new tiny home combining modern luxury with central location adjacent to UVA, central to wineries, and 10 minutes from Monticello. La Casita is design built to offer custom furnishings and luxurious touches. We are in the residential pedestrian-friendly neighborhood of Fry's Spring, near I 64. Walk to restaurants and Scott Stadium. Enjoy all amenities including a high-speed internet.
Popular amenities for holiday rentals near James Monroe's Highland
Condo rentals with Wi-Fi

Cozy getaway with heated floors

The Modern Mountain Condo

Blue Ridge Retreat: Your Cozy Mountain Getaway

Ski-In Ski-Out ~ Mtn Views ~ King Suite

Stylish*Updated*Central*Walk to Slopes*Dogs OK!

Mountain View Condo at Wintergreen, Fireplace

Luxurious Posh Downtown Condo

New Construction! 1 Bed/2 Bath, pet friendly
Family-friendly house rentals

Close to skiing! | King Beds | Fireplace | Hot Tub

Locust Grove Retreat- 3 Bed, 1 Bath, Full Kitchen

Charming Cottage at Golden Hill

Stylish Belmont Studio: Walk to Downtown Mall

The Hummingbird, a cozy quiet, 2 room apartment

10 Vineyards Within 10 Mi, EV charger & Mini Goats

River Vista Cottage | Fenced Yard + Dog-Friendly

The Loft at Minor Mill - Private loft apartment.
Apartment rentals with air conditioning

Close, Spacious, Fully Furnished, Breakfast

Clean, central, spacious, private - UVA/Downtown

Mountain View Nest

Walker's dream. Close to downtown.

*Private Apartment in Downtown Cville*

country garden apartment downtown

Main Street Downtown Balcony Apartment

A private apartment with Self Check-in.
Other great holiday rentals near James Monroe's Highland

Clean, cozy guesthouse near historic downtown mall

The Laurel Hill Treehouse

Beaver Pond Farm - Near Charlottesville

Woolen Mills Cottage- 2 Beds, 1 Bath, Full Kitchen

Hawkwood House King Bedroom

Crozet Cottage | Close to Wineries & DT Crozet

Tranquil Cottage and Art Studio

The Stable
Destinations to explore
- Shenandoah National Park
- Luray Caverns
- Early Mountain Winery
- Downtown Mall
- Lake Anna State Park
- Frontier Culture Museum
- Prince Michel Winery
- Blenheim Vineyards
- Wintergreen Resort
- Cardinal Point Winery
- Glass House Winery
- James Madison University
- Devils Backbone Brewing Co Basecamp
- University of Virginia
- Monticello
- John Paul Jones Arena
- White Lotus Eco Spa Retreat
- Grand Caverns
- The Rotunda
- Cooter's Place
- IX Art Park
- James River State Park
- James Madison's Montpelier
- White Oak Lavender Farm & The Purple WOLF Vineyard




