Too Doo - Vacation Rentals in Monticello
House
- Air Conditioner
- Parking
- Pet Friendly
House
- Parking
- Accessibility
- Security/Safety
Bed & Breakfast
- Air Conditioner
- Parking
- Designated Smoking Area
Apartment
- Air Conditioner
- Parking
- Pet Friendly
House
- Air Conditioner
- Parking
- Pet Friendly
House
- Air Conditioner
- Parking
- Pet Friendly
Hotel
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- TV
- Security/Safety
Apartment
- Air Conditioner
- Parking
- Pool
House
- Air Conditioner
- Parking
- Pet Friendly
House
- Air Conditioner
- Parking
- TV
Apartment
- Air Conditioner
- Parking
- TV
Apartment
- Air Conditioner
- TV
- Security/Safety
House
- Air Conditioner
- Parking
- TV
House
- Air Conditioner
- Pet Friendly
- Designated Smoking Area
House
- Air Conditioner
- Parking
- Pet Friendly
★ Pro Tip: Toodoo makes it easy to compare the best listings on Toodoo homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Toodoo homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Monticello.
Weather in Monticello
View the weather forecast for Monticello before booking your Monticello Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Monticello, VA
Toodoo offers a large selection of top attractions around Monticello. Research things to do on your vacation before you visit Monticello.
University of Virginia
Downtown Mall
John Paul Jones Arena
University of Virginia Hospital
Trump Winery
The Jefferson Theater
Paramount Theater
Charlottesville Pavilion
Pippin Hill Farm & Vineyards
Scott Stadium
Keswick Vineyards and Winery
Michie Tavern
Fashion Square Mall
University Hall at University of Virginia
Jefferson Vineyards
Arcady Vineyard
Corner district
Barracks Road Shopping Center
Carter Mountain Orchard
Rivanna Trails
Monticello Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Monticello?
There are a lot of options in Monticello. If you plan on staying in the Monticello area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Monticello:
- Private Retreat on 10 Acres Minutes from Monticello, Wineries & Charlottesville!
- The Recycled House - Walk Downtown
- NO CLEANING FEE, Off Street Parking, walkable to UVA, Ting Pavilion, Restaurants
- HIDDEN GEM BARN STUDIO WITH A VIEW near Monticello, wineries, with pool
- Bright, Spacious Home Perfect for Groups and Families: 4BR, 5 Beds
- Historic Beauty and Walkable to Everywhere
- UVA Hospital Area Free Guest Parking No Stairs Separate Private Entrance
- Farmhouse On 14 Acres. Close to Monticello & Ash Lawn Highland
- Warner House | Charming Home in Belmont- walk Downtown
- Fairytale Loft Suite | 1 bed, 1 bath Luxury Apartment in Downtown Belmont
How many vacation rentals are available in Monticello?
Currently, the total number of properties listed in 2026 is over 340 in the Monticello area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Monticello.
