
Places to stay near James Monroe's Highland
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Top-rated vacation 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!

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!

Thomas Jefferson Pkwy - Gateway to Monticello
Farmhouse on 14 acres offers closest proximity to Monticello (4 minutes away). Jefferson Vineyard (1 min), Ash Lawn (3 min), Carter's Mountain & Michie Tavern (5 min), Downtown Open-Air Mall (14 min). Relax with a cold drink on the front porch or enjoy views of the mountains and pond from the back deck. There is plenty of space to breathe here. Full kitchen & laundry. Feel free to snack on whatever we have. Great views & country feeling but close to everything. Relax & make yourself at home!

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.

Beaver Pond Farm - Near Charlottesville
Relax at this unique and tranquil getaway. Sit on the screened in porch and enjoy the sights and sounds of nature while you enjoy a beverage. Visit the Downtown Mall, Monticello, a Winery, a Brewery, or UVA (20 min). Enjoy a dip in the pool (JUN-AUG) or relax by the firepit - perhaps joined by a Great Pyrenees for cocktails. Feel like staying in - SmartTVs with YouTubeTV (which includes local channels) and Gig-speed Internet await. Easy checkout. No cleaning fee.

Convenient Rustic Cabin near Wineries
I’m located 6 miles from Scottsville, 15 miles from Charlottesville, 25-30 minute drive. A pasture of cattle is not too far away you can hear the mooing at times and see sightings of deer quite often. It’s a private and quiet location. Two large rivers, James and Rivanna offer recreational activities. Rustic cabin, country located. Clean and cozy with a well stocked kitchen with all your cooking needs. If not, leave suggestions on what is missed. Thank you.

The Loft at Minor Mill - Private loft apartment.
Our place is a newly constructed barn loft in our 1960's barn. Enjoy beautiful views of the surrounding countryside from large windows and a private balcony. The barn is surrounded by our horse pastures and neighboring fields. Self check in with the key lockbox. This loft is separate from the main house where we live. Private parking and entrance for our guests directly outside of barn loft (this is separate from the main house driveway).

Oxford Cottage: Cville’s favorite tiny home!
Tiny living done right! Discover 350 sq ft of stylish simplicity in this thoughtfully designed mini cottage. With an airy entry, cozy living area, smart kitchenette, full bath, lofted sleeping nook, and clever storage, it’s perfect for 1–4 guests seeking a relaxed stay—whether for a romantic retreat, work escape, quick stopover, or lively Charlottesville event like weddings, concerts, or triathlons.

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.

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.

Charming Cottage at Golden Hill
Enjoy our lovely handcrafted cottage in its wooded, peaceful setting with its new keyhole-style herb garden. Just a mile off the Keswick exit of I-64 near Charlottesville, UVA, Monticello, many wineries and historic sites, this conveniently located property includes walking trails, hilarious chickens, beautiful gardens and a new playset for children. High speed internet is an added bonus.
Popular amenities for vacation rentals near James Monroe's Highland
Condo rentals with wifi

Five Minute Walk to Everything!

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

Mountain View Condo at Wintergreen, Fireplace

Luxurious Posh Downtown Condo

New Construction! 1 Bed/2 Bath, pet friendly

2-min drive to slopes, stair-free/free firewood!

The Townie 3 BD/2BA Historic Downtown Building

Sunset Vista Villa, Mountain Views-Close to Slopes
Family-friendly house rentals

3BR / Pets Welcome / Fenced Yard / Fiber Internet

Montrose Manor- In the heart of Belmont!

Newly Built Luxury Home 3min to UVA–Near Downtown

Wakefield Ct | Private Parking spots | Fast WiFi

High Note | Parking X3 | Sleeps 6 | Rivanna Access

The Hummingbird, a cozy quiet, 2 room apartment

One Level Living at Shadwell Terrace

River Vista Cottage with Fenced Yard
Apartment rentals with air conditioning

Close, Spacious, Fully Furnished, Breakfast

*Private Apartment in Downtown Cville*

Charming St. Charles

Main Street Downtown Balcony Apartment

A private apartment with Self Check-in.

Willow Ridge

Black Cat Retreat

UVA Hospital Area Private Guest Parking
Other great vacation rentals near James Monroe's Highland

Clean, cozy guesthouse near historic downtown mall

Downtown studio, walk to corner/downtown mall/UVA

Cavalier Suite | Near UVA | Amenities | Parking

The Laurel Hill Treehouse

Small cozy Cabin in the foothills! Dogs welcome!

Cabin in The Pines

Hawkwood House King Bedroom

Polaroid Provided! | Rooftop Balcony | Stunning
Destinations to explore
- Luray Caverns
- Early Mountain Winery
- The Plunge Snow Tubing Park
- Massanutten Ski Resort
- Prince Michel Winery
- Lake Anna State Park
- The Foundry Golf Club
- Kinloch Golf Club
- Chisholm Vineyards at Adventure Farm
- Wintergreen Resort
- Frontier Culture Museum
- Spring Creek Golf Club
- Blenheim Vineyards
- Farmington Country Club
- Birdwood Golf Course
- Cardinal Point Winery
- Glass House Winery
- The Car and Carriage Caravan Museum
- Monticello
- Meriwether Springs Vineyard and Brewery
- Burnley Vineyards




