
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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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.

Crozet Cottage | Close to Wineries & DT Crozet
Enjoy a cozy getaway at our centrally-located carriage house, in the heart of sought-after Crozet, VA. Completely renovated in 2022, the carriage house feels brand new! Our space offers 1 queen bed and 1 full-bed pull-out couch. The space is .5 miles from downtown Crozet, 2.5 miles to King Family Vineyard and 3.5 miles to Chiles Orchard. It is equipped with a kitchen, a large closet (fits a pack n' play!), high speed internet and Apple TV. We have assigned parking spots in the driveway.

Belmont Private Suite, 1/2 mile to Downtown Mall
Cozy, quiet high-ceiling basement suite located in historic Belmont neighborhood. Private entrance with keypad lock for easy check-in/out. Space includes living area, 1 large bedroom with queen bed (air mattress provided if needed), full bathroom with towels/essentials, coffee maker, electric tea kettle, microwave and mini fridge. Walking distance to Downtown mall and numerous restaurants, coffee shops, and parks nearby. 1-2 mile walk from UVA and 3 miles to Monticello. Free street parking.

Clean, central, spacious, private - UVA/Downtown
This downtown, sparkling clean, basement-level apartment has a private entrance. Centrally located downtown in a quiet historic neighborhood that backs into the beautiful Rivanna trail. Stroll to the famous pedestrian Downtown Mall with fine dining and theaters, and to the brand new Wegman's store and shopping center. Enjoy a 40-minute walk, or 7-minute ride to Scott Stadium, UVA's Rotunda, the UVA Hospital, the "Corner", and much more. *Please read more details provided below*

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.

Unit 1_Expansive Luxury Suite for up to 4 Persons
Take a journey to Albemarle County and experience historical sites and luxurious accommodations. Sonsak is uniquely situated on the Thomas Jefferson Parkway; nears area's most celebrated landmarks, including Monticello - Home of Thomas Jefferson, directly across Michie Tavern and near Ash Lawn - Home of James Monroe, Carter Mountain Orchard and numerous Vineyards. Embark on a 'Journey Through Hallowed Ground', an unforgettable experience that's packed with history and beauty.

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!

Clean, cozy guesthouse near historic downtown mall
You're sure to enjoy this recently built (completed March 2020), private guesthouse in the charming Little High neighborhood near downtown Charlottesville. Cozy yet uncluttered space, high-speed wi-fi, private patio area, and a helpful host make for a pleasant stay in a great location. We are less than a mile from the historic downtown mall, two miles from UVa, four miles from Monticello, and within 15 miles of numerous hikes, vineyards and breweries.

Luxury tiny house 3 min from UVA
La Casita, a new tiny home, combines modern luxury with a prime location near UVA, wineries, and Monticello. Designed to offer custom furnishings and luxurious touches, La Casita is situated in the residential, pedestrian-friendly neighborhood of Fry’s Spring, conveniently located near I-64. Residents can enjoy easy access to restaurants and Scott Stadium. Amenities include high-speed internet and other modern conveniences.

Beautiful, Cozy, Downtown Apt!
Enjoy a stylish experience at this centrally-located place. Beautifully curated apartment with luxury kitchen, tiled bathroom and wonderful deck. It has two split units to keep the place as cool or as warm as you desire. Semi-firm Queen mattress for a perfect nights sleep. A short walk to the Historic Downtown Malls shops and restaurants and The Rivanna River for tubing, swimming, biking, picnics.

2 King/1 Twin Near Downtown & UVA
⭐️Two bedroom lower-level apartment (2 king beds, 1 twin XL, 1 toddler bed, 1 pack-n-play) in a quiet neighborhood near downtown! ⭐️Our guests rave about the excellent value, amenities, & cleanliness! 📍1 mile from UVA Hospital and Downtown Mall 📍1.6 miles from UVA ⭐️No smoking! ⭐️Please read note about the slope to the entrance 🟢The person booking must be present during the stay
Popular amenities for holiday rentals near James Monroe's Highland
Condo rentals with Wi-Fi

Cozy getaway with heated floors

Blue Ridge Retreat: Your Cozy Mountain Getaway

Cozy Condo - Sleeps 4

Five Minute Walk to Everything!

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

Eight Minute Walk to Everything

Luxurious Posh Downtown Condo

Mountaintop Overlook – Updated 2BR w/ Deck & Views
Family-friendly house rentals

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

Rooftop*Mountains*Lake/Near Monticello/DT/Wineries

Kid and Family Friendly Downtown

Cozy convenient home in Bellmont

Charming Cottage at Golden Hill

The Hummingbird, a cozy quiet, 2 room apartment

Tranquil Estate Cottage + Art Studio

Stylish Belmont Studio: Walk to Downtown Mall
Apartment rentals with air conditioning

UVA, Downtown Mall, Historic Area

Mountain View Nest

Walkable/Peaceful/Spacious Suite/Downtown/UVA/1 BR

country garden apartment downtown

A private apartment with Self Check-in.

Black Cat Retreat

The Octagon ~ bright/spacious 2BR Downtown Retreat

Basic Belmont Apt w/ Air Hockey & near Downtown!
Other great holiday rentals near James Monroe's Highland

Garden Apt | Lux Extended Stay in Downtown Belmont

Terrace Level Apartment Walking Distance to UVA

Comfortable North Downtown Getaway

The Gardener’s Cottage

Sunny studio apartment near UVA/Downtown

Hawkwood House King Bedroom

Sunny private studio, walk to the University

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




