
Places to stay near Monticello
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Top-rated holiday rentals near Monticello
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Belmont Home with Hot Tub - steps from Downtown
The perfect destination for your Charlottesville visit in the hip neighborhood of Belmont, where you can read on the loggia with great views or in the hot tub on the patio. From this modern home, you can walk to the best restaurants the city has to offer as well as the popular Downtown Mall and IX Art Park. The University of Virginia and Monticello are each just a short drive, and the home is convenient to the Monticello Wine Trail and Skyline Drive. See below for link to basement apt. listing.

Jefferson Cottage quiet farm close to everything
The cottage circa 1802 offer a peaceful private setting on a historic horse farm once part of Monticello with close proximity to wineries (10 minutes), town (12 minutes), Rivanna River borders the property, Carter mountain (8 minutes) and many other activities. A "Jimmy Buffet" salt water pool complex has a private Jacuzzi for each unit, double bars, two fire pits, frig ,full bath/shower/changing room) There is a private lake (catch and release fishing) and many places to walk on the property.

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.

Mountain Overlook House - Blue Ridge Parkway
Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Shenandoah Stargazer with Sauna
Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

Honey B - Beautiful small house 9 minutes from UVA
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.

CloudPointe Retreat
Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

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).

Cozy Wine Country Escape | Near Clifton Inn
Tucked in Keswick, Virginia, this renovated 2-bedroom, 850 sq/ft suite is your perfect wine country escape. Two queen bedrooms, full kitchen, living room, and private entrance — all your own. Less than a quarter mile from Clifton Inn, minutes from Keswick Hall, and surrounded by award-winning wineries. Downtown Charlottesville is 15 min away, Monticello just 7. When the day winds down, find your spot in the hammock under the trees.

10 Vineyards Within 10 Mi, EV charger & Mini Goats
Upscale boutique Carriage House on a 25-acre farm in Charlottesville Wine Country. Minutes from top vineyards, this light-filled retreat features elegant rustic design, new furnishings, and spa-like comfort. Enjoy visits with Nigerian dwarf goats and free-ranging chickens. Perfect for romantic getaways or remote work, with WiFi, cozy touches, and the beauty of nature all around. Tesla wall connector charger available for guests.

Tranquil Estate, Cottage, Vineyards and C'ville
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"
Popular amenities for holiday rentals near Monticello
Condo rentals with Wi-Fi

Where the Trail Ends

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

Mountain Views

Luxurious Posh Downtown Condo

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

The Townie 3 BD/2BA Historic Downtown Building

Panoramic Sunsets, Mountain Views, Private Deck.

Cozy Condo on the mountain at Wintergreen!
Family-friendly house rentals

3BR / Pets Welcome / Fenced Yard / Fiber Internet

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

Farm Cottage w. Blue Ridge views 20 mins from SNP

Walk DT | Pets | Soaking Tub | Parking

Spaniel Hill; cozy hilltop home w privacy & views

Firnew Cottage

River Vista Cottage | Pet-Friendly + Fenced Yard

Cozy Downtown Cottage!
Apartment rentals with air conditioning

Heart of Belmont ~ 15 min walk downtown, free park

Patio Downtown Retreat

Belmont BnB ~ 2BR/1BA ~ Comfort & Convenience

Parker Mountain Carriage House Near SNP, UVA & JMU

The Barn at Haden near Wineries and C'ville

Charming St. Charles

Private apartment in Charlottesville / Belmont

Main Street Downtown Balcony Apartment
Other great holiday rentals near Monticello

Ultimate cabin in the mountains

Beaver Pond Farm - Near Charlottesville

Sun Cottage in Downtown Charlottesville

Adorable cottage steps from Grounds

Delightful one bedroom treehouse with king bed

Cozy Farm Apt near Cville•wineries, mt. views

Charlottesville Cottage-2 king beds

100% Solar Home! Guilt Free Living 1 mile from DT
Destinations to explore
- Shenandoah National Park
- Luray Caverns
- Lake Anna State Park
- Early Mountain Winery
- University of Virginia
- Downtown Mall
- Wintergreen Resort
- Devils Backbone Brewing Co Basecamp
- Glass House Winery
- Blenheim Vineyards
- Prince Michel Winery
- Cardinal Point Winery
- The Rotunda
- James Monroe's Highland
- Frontier Culture Museum
- John Paul Jones Arena
- Grand Caverns
- White Oak Lavender Farm & The Purple WOLF Vineyard
- James Madison University
- IX Art Park
- The Plunge Snow Tubing Park
- Massanutten Indoor WaterPark
- James River State Park
- James Madison's Montpelier





