Best Vacation Homes in Monticello
2000 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $272/Night
For 7 Nights US $1,901
505.9 ft²
8 Guests
4 Bedrooms
6 Bathrooms
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Balcony/Terrace
- View
US $194/Night
For 7 Nights US $1,358
US $88/Night
For 7 Nights US $619
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $199/Night
For 7 Nights US $1,392
1550 ft²
8 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $271/Night
For 7 Nights US $1,897
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Private Pool
- Hot Tub
- Pool
US $161/Night
For 7 Nights US $1,126
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $180/Night
For 7 Nights US $1,257
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $251/Night
For 7 Nights US $1,754
Monticello Luxury Rentals
14 Guests
6 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
US $2,362/Night
For 7 Nights US $16,537
4187 ft²
6 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Spa
- Fireplace/Heating
US $777/Night
For 7 Nights US $5,437
10 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
Bed & Breakfast
- Hot Tub
- Fireplace/Heating
- Air Conditioner
US $626/Night
For 7 Nights US $4,384
13 Guests
4 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $559/Night
For 7 Nights US $3,912
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $539/Night
For 7 Nights US $3,776
12 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Other
- Fireplace/Heating
- Pool
- Ocean View
US $454/Night
For 7 Nights US $3,176
1800 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $437/Night
For 7 Nights US $3,056
3595.15 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $420/Night
For 7 Nights US $2,942
Monticello Pet Friendly Vacation Rentals
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $114/Night
For 7 Nights US $798
495.14 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $130/Night
For 7 Nights US $912
3600 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $357/Night
For 7 Nights US $2,496
1797.57 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Pet Friendly
- Parking
- Air Conditioner
US $230/Night
For 7 Nights US $1,612
1850 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $219/Night
For 7 Nights US $1,531
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Air Conditioner
US $105/Night
For 7 Nights US $735
2583 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $369/Night
For 7 Nights US $2,583
8 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $329/Night
For 7 Nights US $2,300
Monticello Large Vacation Homes
3000 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $203/Night
For 7 Nights US $1,418
1700 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $176/Night
For 7 Nights US $1,231
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Internet
US $293/Night
For 7 Nights US $2,054
4200 ft²
6 Guests
8 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $416/Night
For 7 Nights US $2,912
14 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $150/Night
For 7 Nights US $1,050
Why Choose Rent By Owner for your Monticello Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Monticello
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, whether you're seeking outdoor adventures or a peaceful retreat in this charming destination.
Peak Season Highlights
Summer (June to August)
During the peak summer months, the region experiences warm weather ideal for outdoor activities and exploring local scenery. This is a popular time to visit, so booking your vacation rental early ensures you secure the best property options.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
Fall (September to October)
Autumn brings mild temperatures and vibrant foliage, making it an attractive season to enjoy the area's natural beauty. The pleasant weather attracts many visitors, so early reservations for your vacation rentals are recommended to avoid limited availability.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter months see fewer visitors as temperatures drop, offering a peaceful retreat with crisp air and potential snow-covered landscapes. This is an ideal time to find more affordable vacation rental options with fewer crowds.
Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 15°F
Spring (March to May)
Spring features gradually rising temperatures and blooming surroundings, making it a quieter time to experience the area’s natural charm. Booking ahead can help you find cozy vacation rentals at better rates during this off-peak period.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F
Weekly Weather Forecast for Monticello
How to Book Your Monticello Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Monticello
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to scenic outdoor spaces with private patios or decks for relaxing amidst the natural beauty.
- Take advantage of spacious yards perfect for outdoor activities and family gatherings.
- Make the most of community or private swimming pools available on site or nearby.
- Experience outdoor dining options such as grills or picnic areas, ideal for meals in the fresh air.
- Explore well-maintained walking or biking trails that showcase the region’s picturesque landscape.
- Relax by a cozy fire pit during cool evenings, ideal for socializing or stargazing.
- Access to water features like lakes or ponds for activities such as fishing or kayaking, common here in the area.
Top Attractions Around Monticello
What attractions are nearby?
Here, you can enjoy a variety of outdoor activities such as hiking and fishing just minutes from your vacation rental, allowing you to fully experience the natural beauty of the region.
Family Activities
- Wildlife Observation at Grand River Marsh Wildlife Area: Enjoy a family-friendly day exploring the diverse bird species and natural scenery that make this regional wildlife area a must-visit outdoor activity.
- Fishing at Lake Monticello: Spend relaxing hours casting lines in the tranquil waters of Lake Monticello, perfect for creating memorable bonding experiences with your loved ones.
- Hiking and Nature Walks in Central Park: Discover scenic trails and open spaces ideal for family strolls and nature discovery within this local park's peaceful environment.
- Visiting Local Farmers Markets: Experience the region’s fresh produce and handcrafted goods during weekend markets, offering a delightful cultural immersion for all ages.
Adult Activities
- Exploring the local vineyards and wineries: You can enjoy tastings and tours at the nearby wineries, experiencing the region's renowned wine culture firsthand.
- Golfing at scenic courses: Tee off on beautifully maintained golf courses that offer stunning views of the surrounding countryside, perfect for a relaxing day outdoors.
- Visiting historic sites and museums: Discover the area's rich history through local museums and historic landmarks that provide insight into the community's heritage.
- Enjoying outdoor recreation in natural parks: Spend your days hiking, biking, or picnicking in regional parks that showcase this destination’s scenic beauty and tranquil environment.
Monticello Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Popular Seasons: Book your stay early to secure the best vacation rentals during peak times in this charming area.
- Explore Local Dining Options: Take advantage of nearby eateries to enjoy regional flavors without straying far from your rental property.
- Make the Most of Outdoor Activities: Utilize the region’s natural landscape by scheduling outdoor adventures directly accessible from your accommodation.
- Check Amenities and Services: Select properties that offer the comforts and conveniences you need to enhance your experience here.
Transportation Options
- Car Rentals: Renting a car in this area offers you the freedom to explore nearby attractions and scenic spots at your own pace.
- Local Taxis and Rideshares: Convenient for quick trips within the region, taxis and rideshare services provide reliable transportation directly from your vacation rental.
- Public Transit: The local bus service connects key points around here, making it easy to navigate the destination without needing a vehicle.
- Biking and Walking: The region features picturesque paths and trails, perfect for exploring the area on foot or by bike during your stay.
Local Customs Options
- Traditional Wisconsin Hospitality: Locals take pride in welcoming visitors with warm, neighborly gestures that reflect the region’s friendly spirit.
- Community Events and Festivals: Participating in annual gatherings like local fairs showcases the area's commitment to preserving its cultural heritage.
- Respect for Nature and Outdoor Activities: The community values outdoor pursuits, encouraging responsible recreation amidst the area's scenic landscapes.
- Emphasis on Local Cuisine: Visitors often enjoy tasting regional specialties at gatherings and eateries that celebrate the area's culinary traditions.
Monticello Vacation Rental Frequently Asked Questions
1. 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:
- A Home Away from Home in the Quaint Village of New Glarus
- 3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
- MJ's Penthouse ,a piece of paradise on Monroe's historic square
- HOLY COW! Guest Haus in The Heart of New Glarus
- Beautifully updated home close to downtown New Glarus
- Beautiful New Glarus, WI Apartment
- Beautiful two story, downtown home, one block from the Square,
- Sugar River Suite - Your Sweet Escape in the Heart of it All!
- The Dairy at the Wegmueller Farm - stay on a Wisconsin farm!
- Relax on the Sugar River in this beautiful newly renovated building
2. Which vacation homes in Monticello are best for families?
If you are looking for a family-friendly vacation home in Monticello, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Monticello:
3. How many Rentbyowner vacation rentals are available in Monticello?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 52 in the Monticello area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Monticello.
4. What is the cancellation policy for vacation rentals in Monticello, Wisconsin?
Cancellation policies vary depending on the property listing. It’s important to review the specific cancellation terms outlined in each rental agreement or contact the property owner directly for detailed information before booking.
5. Are there any amenities included with vacation rentals in the area?
Amenities differ between listings, so it’s advisable to check each property's description to see what is provided. Common features include Wi-Fi, kitchens, and outdoor spaces, but confirm with the owner for your preferred amenities.
6. How do I ensure my booking in Monticello is secure and reliable?
Book through a trusted platform that verifies listings and offers secure payment options. Always read reviews and verify details with the property owner to ensure a seamless and trustworthy experience.
7. What is the check-in and check-out process for vacation rentals here?
Check-in and check-out procedures are specified within each listing. Contact the host ahead of time to confirm arrival times, access instructions, and any specific requirements to ensure a smooth stay.
8. Can I modify or cancel my reservation once booked in this region?
Modification and cancellation policies depend on the individual property. Review the terms on the listing page or contact the host directly to understand your options for changing or canceling your reservation.
Monticello Top Rated Vacation Rentals
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Other
- Hot Tub
- Fireplace/Heating
- Pool
US $138/Night
For 7 Nights US $966
US $137/Night
For 7 Nights US $958
301.39 ft²
10 Bathrooms
Family Friendly
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $92/Night
For 7 Nights US $645
247.57 ft²
11 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $168/Night
For 7 Nights US $1,176
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
US $267/Night
For 7 Nights US $1,867
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Private Pool
- Fireplace/Heating
- Pool
US $100/Night
For 7 Nights US $700
800 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Spa
- Fireplace/Heating
- Pool
US $154/Night
For 7 Nights US $1,081
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Pool
US $215/Night
For 7 Nights US $1,508
