
Places to stay near James Monroe's Highland
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Top-rated holiday rentals near James Monroe's Highland
Guests agree: these stays are highly rated for location, cleanliness and more.

Rooftop*Mountains*Lake/Near Monticello/DT/Wineries
Spacious modern house with a large furnished rooftop deck overlooking Monticello & Carter Mountain. Not one, but two spacious master suites (one on each floor) with attached decks, plus additional two bedrooms and a full bathroom on the 2nd floor. Located in a quiet neighborhood and 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.

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!

Idyllic Cottage Retreat
⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

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!

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.

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.

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.

The Octagon ~ bright/spacious 2BR Downtown Retreat
Bright and spacious two bedroom apartment with ample free off-street parking, two blocks from the Historic Downtown Mall. Walk to shops, restaurants, coffee, yoga, and music venues. 10 minute walk ~ the historic downtown mall 5 min ~ Rivanna River - walking trail and tubing/kayaking/SUP 5-10 min ~ UVA 5-10 min ~ Monticello Trail 10-15 min ~ Monticello 15-30 min ~ MANY popular wineries, breweries, and hiking in the Blue Ridge Mountains

Tranquil Estate Cottage + Art Studio
Guests consistently say the sunsets alone are worth the stay! We've had anniversary trips, proposals, creative retreats, and gal pal gatherings looking for fun. This area boasts award winning vineyards, gardens and history buffs enjoy Monticello and Montpelier. Our peaceful cottage offers the perfect space for couples, creatives, and anyone craving beauty just 10 minutes from downtown C'ville. *Read "Your Property"

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.
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

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

Mountaintop Overlook – Updated 2BR w/ Deck & Views

Luxurious Posh Downtown Condo
Family-friendly house rentals

Woodwind Cottage

Kid and Family Friendly Downtown

Charming Cottage at Golden Hill

10 Vineyards Within 10 Mi, EV charger & Mini Goats

One Level Living at Shadwell Terrace

River Vista Cottage | Fenced Yard + Dog-Friendly

The Loft at Minor Mill - Private loft apartment.

Thomas Jefferson Pkwy - Gateway to Monticello
Apartment rentals with air conditioning

Charming & Convenient Guest Suite minutes to UVA

*Private Apartment in Downtown Cville*

So Walkable, 1 Spacious Bedroom Suite/Downtown/UVA

Charming St. Charles

country garden apartment downtown

A private apartment with Self Check-in.

Black Cat Retreat

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

Terrace Level Apartment Walking Distance to UVA

Cavalier Suite | Near UVA | Amenities | Parking

Beaver Pond Farm - Near Charlottesville

The Laurel Hill Treehouse

Delightful one bedroom treehouse with king bed

Relaxing 2BR CABIN, 12 acres, dog friendly, hiking

Hawkwood House King Bedroom

Jefferson Cottage quiet farm close to everything
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
- Cardinal Point Winery
- Glass House Winery
- University of Virginia
- John Paul Jones Arena
- Devils Backbone Brewing Co Basecamp
- James Madison University
- White Lotus Eco Spa Retreat
- Monticello
- The Rotunda
- Cooter's Place
- Grand Caverns
- IX Art Park
- White Oak Lavender Farm & The Purple WOLF Vineyard
- James River State Park
- Appomattox Court House National Historical Park




