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

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.

The Belmont Loft ~ 15 min walk downtown, free park
Stay here! In the cutest house in Charlottesville's most beloved neighborhood. You'll be in the heart of Belmont, just steps from some of the best restaurants in Cville, and a few blocks from the historic Downtown Mall - restaurants, shops, coffee, yoga, and music venues. 10 min walk ~ downtown mall 5 min ~ Rivanna River - trail and tubing/kayaking/SUP 5-10 min ~ UVA 5-15 min ~ Monticello/Monticello Trail 15-30 min ~ MANY popular wineries, breweries, and hiking in the Blue Ridge Mountains

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.

3BR / Pets Welcome / Fenced Yard / Fiber Internet
Sitting atop the neighborhood, Monticello 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. Freshly painted. Big Green Egg grill

Adorable cottage steps from Grounds
A cozy Milton Grigg designed cottage and detached carriage house three minutes walk to the Lawn and ten minutes walk to the Stadium. Nestled in a wooded neighborhood. Perfect for visiting parents, UVA chapel weddings, med student rotations, and football games. NOTE: The cottage sleeps five adults and the carriage house two adults. There is one bathroom in the cottage and one in the carriage house. Please read through all the information in the 'Description' section below before booking.

Ivy Rose Cottage nestled b/t Cville & Vineyards
The Ivy Rose Cottage bestows an exceptional ambiance that will captivate your heart. Whisk yourself away to this two bedroom cottage located in Ivy halfway between the Shenandoah Park/Brewery Trail and Charlottesville, home of UVA. The Ivy Rose Cottage, designed and handbuilt by the hosts, is an enchanting mix of cypress, timber frame, copper trellis work, pergolas and other architectural treasures. Fully equipped kitchen and a washer/dryer for those lengthier stay conveniences.

Luxury Cottage | Outdoor Tub + Mountain Views
Soak in a private outdoor bathtub beneath the stars, wake to mountain views from your king bed, and open an entire wall of glass to bring the Blue Ridge Mountains inside. Welcome to The Cottage at Perkins Hollow Retreat! Located in Nelson County, just minutes from the Nelson 151 Brew Trail, award-winning wineries, breweries, hiking, and only 25 minutes from Charlottesville, The Cottage is the perfect destination for a romantic getaway, anniversary, honeymoon, or peaceful retreat.

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.

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." Pool is available most summer stays. Thank you!

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.
Popular amenities for vacation rentals near Monticello
Condo rentals with wifi

Mountain Views

Panoramic Peak: Wintergreen Condo with Views

Luxurious Posh Downtown Condo

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

Extremely private, HOA pool/stair-free entry

The Townie 3 BD/2BA Historic Downtown Building

Cozy Comfort with a View - Wintergreen Resort

Panoramic Sunsets Mountain Views Pool $99 Midweek
Family-friendly house rentals

Mountain View Rambler | 3 Bedrooms | Private deck

Walk DT | Pets | Soaking Tub | Parking

Perfect getaway among the orchards of Batesville

Spaniel Hill; cozy hilltop home w privacy & views

10 Vineyards Within 10 Mi, EV charger & Mini Goats

Downtown Retreat | Fenced Yard + Pets Welcome

Cozy Downtown Cottage!

The Loft at Minor Mill - Private loft apartment.
Apartment rentals with air conditioning

Boho Vibe: Walkable, Quiet, Historic Downtown

Patio Downtown Retreat

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

Parker Mountain Carriage House Near SNP, UVA & JMU

2 King Beds | 8 Min to UVA | Sleeps 5

The Barn at Haden near Wineries and C'ville

Private apartment in Charlottesville / Belmont

Free Downtown Parking | Ping Pong | Steps to UVA
Other great vacation rentals near Monticello

Centrally located, cozy, quiet, upscale studio apt

Ultimate cabin in the mountains

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Do Drop Inn - charming 2BR bungalow

Tugboat/Private Lake - Farm Animals - Fish, Swim,

Charlottesville Cottage-2 king beds

Walk Downtown and to UVA

Historic HomeTract Cottage UVA/Charlottesville/Ivy
Destinations to explore
- Shenandoah National Park
- Luray Caverns
- Lake Anna State Park
- Early Mountain Winery
- University of Virginia
- Wintergreen Resort
- Devils Backbone Brewing Co Basecamp
- Glass House Winery
- Cardinal Point Winery
- Blenheim Vineyards
- Prince Michel Winery
- The Rotunda
- Frontier Culture Museum
- Downtown Mall
- James Monroe's Highland
- John Paul Jones Arena
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Grand Caverns
- IX Art Park
- James River State Park
- Massanutten Indoor WaterPark
- Appomattox Court House National Historical Park
- The Plunge Snow Tubing Park
- James Madison's Montpelier





