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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Top Guest favourite
Apartment in Charlottesville
4.98 out of 5 average rating, 248 reviews

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!

Top Guest favourite
Home in Keswick
5 out of 5 average rating, 113 reviews

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.

Top Guest favourite
A welcoming living area is highlighted by a comfortable couch, complemented by a decorative pillow. Natural light enters through windows adorned with light curtains, creating an airy feel. A stylish area rug adds warmth, while a lamp and small plant enhance the inviting atmosphere.
Guesthouse in Crozet
4.98 out of 5 average rating, 209 reviews

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.

Guest favourite
A wooden coffee table displays potted plants, offering a touch of greenery to the living area. In the background, a small dining table with chairs is positioned near a window, where natural light enhances the warmth of the space.
Home in Charlottesville
4.95 out of 5 average rating, 148 reviews

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.

Guest favourite
A well-lit living area features a comfortable sofa, two patterned chairs, and a coffee table. A television is placed on a white entertainment unit, while soft lighting from nearby lamps creates a cozy ambiance. Light wood flooring complements the neutral color scheme.
Apartment in Charlottesville
4.83 out of 5 average rating, 235 reviews

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*

Top Guest favourite
A serene patio area features a small round table surrounded by two black chairs. Lush greenery and a pathway visible in the background enhance the tranquil setting, with garden views inviting relaxation.
Cottage in Charlottesville
5 out of 5 average rating, 181 reviews

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.

Guest favourite
An aerial view of a grand historical building is surrounded by lush greenery. The structure features a distinctive architectural design, with a circular entrance and multiple columns. Rolling hills and a serene landscape are visible in the background, highlighting the natural beauty of the location.
Home in Charlottesville
4.98 out of 5 average rating, 140 reviews

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.

Top Guest favourite
Apartment in Charlottesville
4.9 out of 5 average rating, 273 reviews

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!

Top Guest favourite
The exterior of the guesthouse is presented, showcasing a modern structure with three large glass doors. A stone patio area is depicted, featuring two outdoor chairs and a fire pit with kindling. Soft outdoor lighting enhances the serene environment among lush greenery.
Guesthouse in Charlottesville
4.98 out of 5 average rating, 104 reviews

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.

Top Guest favourite
The exterior of La Casita features a modern design with smooth gray siding and large windows. A manicured green lawn surrounds the home, with blooming trees providing shade. A small patio area with chairs is visible, inviting outdoor relaxation.
Guesthouse in Charlottesville
5 out of 5 average rating, 189 reviews

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.

Guest favourite
A spacious living area is illuminated by natural light, featuring a modern sectional couch in blue. The room showcases exposed wooden beams along the ceiling and a round area rug with intricate patterns. A small coffee table and vibrant accent pillows add inviting touches.
Apartment in Charlottesville
4.94 out of 5 average rating, 132 reviews

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.

Top Guest favourite
Apartment in Charlottesville
4.97 out of 5 average rating, 435 reviews

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