
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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Historic cottage with stunning mountain views
Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

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.

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!

Private Apt in Historic C'ville Home (Lane Side)
Looking for a place in C'ville close to everything? Look no further. This newly furnished apartment, which comes with high speed internet, a Smart TV, and access to a swimming pool, is just a short walk away to the Historic Downtown Mall. It is a short 5 minute drive to the UVA hospital/campus, and is within reasonable driving distance to the area's many wineries and breweries. Nestled in the heart of the city, and attached to a historic C'ville home, this apt is an excellent place to stay.

Rooftop*Mountains*Lake/Near Monticello/DT/Wineries
Spacious modern house with a large furnished rooftop deck overlooking Monticello & Carter Mountain. Two spacious primary bedroom suits (one on each floor) with attached decks, plus additional two bedrooms and a full bathroom on the 2nd floor. Located in a quiet neighborhood. Backs up to a lake for beautiful views and tranquil environment. Convenient location - minutes away from Monticello (2 mi/4 min), downtown (2.5 mi/6 min), UVA (3 mi/9 min), wineries (closest: 3.5 mi/5 min) & breweries.

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.

Mountain-view hot tub near downtown Cville
The Inner Hippie Garden is a studio suite in a quiet neighborhood fitting two people comfortably. Minutes from vibrant historic downtown Charlottesville and vineyards, wineries and music halls. Check out the Inner Hippie Guidebook in listing. Man-cave for book and 60s music -lovers, full bathroom with tub/shower. Bed and living room space are separated by shelving unit (see photos) Queen bed (see photos) Private Hottub overlooks the mountain.

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).

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.
Popular amenities for holiday rentals near James Monroe's Highland
Condo rentals with Wi-Fi

The Modern Mountain Condo

Blue Ridge Retreat: Your Cozy Mountain Getaway

Eight Minute Walk to Everything

Mountain Views

Luxurious Posh Downtown Condo

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

The Townie 3 BD/2BA Historic Downtown Building
Family-friendly house rentals

3BR / Pets Welcome / Fenced Yard / Fiber Internet

Cozy 3 bedroom home near UVa and Downtown Mall.

Mountain View Rambler | 3 Bedrooms | Private deck

Charming Cottage at Golden Hill

Wine Cellar Cottage | Parking | Quiet but Walkable

Spaniel Hill; cozy hilltop home w privacy & views

The Hummingbird, a cozy quiet, 2 room apartment

Tranquil Estate Cottage + Art Studio
Apartment rentals with air conditioning

UVA, Downtown Mall, Historic Area

Heart of Belmont ~ 15 min walk downtown, free park

Patio Downtown Retreat

Entire 1st Floor of 2 Story Home!

The Barn at Haden near Wineries and C'ville

Charming St. Charles

Historic Beauty and Walkable to Everywhere

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

The Cottage at Hardware Hills Vineyard

Cottage in the Country (close to UVA!)

Bluebird Cottage B: Quiet, Firepit, Patio, Games

Cavalier Suite | Near UVA | Amenities | Parking

Sun Cottage in Downtown Charlottesville

Redbud Garden Suite

Delightful one bedroom treehouse with king bed

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




