
Places to stay near Monticello
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Top-rated holiday rentals near Monticello
Guests agree: these stays are highly rated for location, cleanliness and more.

Rooftop*Mountains*Lake/Near Monticello/DT/Wineries
Spacious modern house with a brand new rooftop deck overlooking Carter Mountain and Monticello. 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 from each level 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 (3.5 mi/5 min+) & breweries.

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!

Walk DT | Pets | Soaking Tub | Parking
The High‑Note Craftsman Cottage – live like a local in downtown Charlottesville Stay in a charming and pet friendly Craftsman cottage just minutes from Charlottesville’s Downtown Mall. Enjoy a soaking tub, fast Ting fiber Wi-Fi, and rare free parking — perfect for couples, families, and remote work travelers. This bright, comfortable home blends historic character with modern amenities, creating the ideal base for exploring Charlottesville, UVA, wineries, and the Blue Ridge Mountains.

3BR / Pets Welcome / Fenced Yard / Fiber Internet
Sitting atop the neighborhood, Monticello mountain can be seen from our Ridgetop home. Convenient to all parts of Charlottesville, including Downtown, UVA, and Hospitals. Local parks offer swimming, boating, & are all walkable. The fenced yard allows for a safe space for dogs and the private patio is perfect for relaxing. The home offers an open design in the kitchen, living & dining room. Bath has a modern tile with a jacuzzi tub. Fast TING fiber internet. Big Green Egg grill

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.

Sun Cottage in Downtown Charlottesville
Solar powered cottage with 15 foot ceiling, sleeps four, This unique place has a style all its own. Italian fold out couch and a loft. kitchen and outdoor deck. It Is 75 feet from our house. We are 1.0 mile from the Downtown Mall of Charlottesville in Historic Woolen Mills, 5 blocks from the Rivanna River and Park. Off street parking, 250 sq ft plus loft. Has lots of light. Enjoy fresh eggs from our chickens!there is so much in our area from hiking to eating to contemplating

Cowboy cottage-hot tub on farm close to everything
Chill out at this private unique and tranquil getaway on a historic farm close to everything. The fully renovated and modernized western themed cottage will take you back in time. The Farm once owned by Thomas Jefferson has close proximity to 14 wineries (15 minutes) 15 breweries/cideries (15 minutes) town (12 minutes) Monticello (next door neighbor) Rivanna River (borders the farm) Carter Mountain (8 minutes) Clifton Inn (2 minutes) and many other close by activities.

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).

Spacious home with vintage character
3 BR shabby chic home sleeps 6 at base price. (Up to 9 at $30/night per extra guest). We've divided our enormous old house just outside of Charlottesville into two completely self-contained solar powered homes. EV charging available at no extra charge. 12 min to downtown, 15 min to Monticello or UVA. Convenient to the region's best wineries and right off one of the most beautiful scenic byways in Virginia. Sunny walkout deck with grill.

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.

Tranquil Estate Cottage | Vineyards & 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." Thank you!

Cozy Downtown Cottage!
Enjoy a relaxing stay at this centrally-located cottage in the heart of Downtown Charlottesville’s Belmont neighborhood. Close to Uva and a 3 minute drive to the Downtown Mall. Easy access to 64 and a few miles to Monticello and Carter’s Mountain Orchard. Two bedrooms and a fully equipped kitchen. Uva centric and Charlottesville pop art throughout. This Belmont beauty is reservation ready!
Popular amenities for holiday rentals near Monticello
Apartment rentals with wifi

The Townie 3 BD/2BA Historic Downtown Building

Luxurious Posh Downtown Condo

1 bedroom condo, close to hikes & breweries & pool

Luxury Condo in the Sky! Finest in Wintergreen!

Panoramic Sunsets Mountain Views Pool $99 Midweek

BlueRidge Getaway- Dog Friendly

Cozy Condo on the mountain at Wintergreen!

3 BR 3 BA, 2 story condo in Highlands
Family-friendly house rentals

Cavalier Cottage-3 BR/Bath, Calm Amid UVA Grounds

The Pop Inn | Perfect for your group getaway

Walk Downtown | Off-Street Parking | Sleeps 6

10 Vineyards Within 10 Mi, EV charger & Mini Goats

West Wing

Scenic Private Farm House Great for Large Groups

The Cherry Tree, downtown estate, 8 parking spaces

Charlottesville Bungalow close to UVA
Apartment rentals with air conditioning

*Private Apartment in Downtown Cville*

Beautiful, Cozy, Downtown Apt!

On Downtown Mall | Huge | King Beds | UVA | Coffee

Heart of Belmont ~ 15 min walk downtown, free park

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

Modern Belmont home - steps from Downtown Mall!

The Barn at Haden near Wineries and C'ville

Walkable/Peaceful/Spacious Suite/Downtown/UVA/1 BR
Other great holiday rentals near Monticello

pink cottage @ locust grange

Adorable cottage steps from Grounds

Do Drop Inn - charming 2BR bungalow

Charlottesville Cottage-2 king beds

Terrace Level Apartment Walking Distance to UVA

Sunny private studio, walk to the University

Hawkwood House King Bedroom

Ivy Rose Cottage nestled b/t Cville & Vineyards
Destinations to explore
- Shenandoah National Park
- Luray Caverns
- Lake Anna State Park
- Early Mountain Winery
- University of Virginia
- Devils Backbone Brewing Co Basecamp
- Wintergreen Resort
- Glass House Winery
- Cardinal Point Winery
- Blenheim Vineyards
- James Madison University
- Prince Michel Winery
- The Rotunda
- Downtown Mall
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Frontier Culture Museum
- John Paul Jones Arena
- IX Art Park
- James Monroe's Highland
- Grand Caverns
- James River State Park
- Massanutten Indoor WaterPark
- Appomattox Court House National Historical Park
- The Plunge Snow Tubing Park





