Monticello Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Monticello vacation rentals

A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

1. Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (28 reviews)
"Amazing location, nicely furnished and cozy!"
United States
Heather & Nick V.
$238 nightly
The price is $263
Nov 8 - Nov 9
Total with taxes and fees
Charming Downtown Two Bedroom w/ Fireplace
A spacious living area with a wooden dining table, a sofa, and a hanging chair. There are large windows providing natural light and a view of the outside.

2. MJ's Penthouse ,a piece of paradise on Monroe's historic square

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (115 reviews)
"The Penthouse is beautiful and the location is unbeatable! We had a wonderful stay and can't wait to come back."
United States
Andie
$237 nightly
The price is $260
Nov 8 - Nov 9
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A spacious kitchen with wooden cabinets, a central island, and a dining area with a table and chairs.

3. Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"Great property and host! Would stay there again."
United States
Ann S.
$218 nightly
The price is $239
Nov 9 - Nov 10
Total with taxes and fees
Lookout Loft over the Monroe Square
A large, two-story log cabin with a stone chimney, a front porch with outdoor seating, and a snow-covered yard leading to a fire pit.

4. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (15 reviews)
"We love this property on the Sugar River. Very spacious, rustic but with all the modern amenities. Beautiful view of the water and lots of wildlife in area. "
United States
Lisa and Peter R.
$699 nightly
The price is $737
Nov 9 - Nov 10
Total with taxes and fees
Lake Cabin | Sauna · River · Game Room
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

5. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (59 reviews)
"Enjoyed the county setting and seeing the cranes and hearing the rooster crow!"
United States
Elizabeth C.
$115 nightly
The price is $121
Nov 8 - Nov 9
Total with taxes and fees
A Room with a View
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

6. The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
9.8 out of 10, Exceptional, (34 reviews)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
$214 nightly
The price is $243
Nov 21 - Nov 22
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

7. Hamilton Goebel House 816 E Louisa St Darlington Wi

Hamilton Goebel House 816 E Louisa St Darlington Wi
Darlington
9.8 out of 10, Exceptional, (54 reviews)
"Three couples stayed at this property. Very comfy beds. We all enjoyed our stay and already have plans to stay again in the fall. It is also close to the trails."
United States
Danette M.
$221 nightly
The price is $242
Nov 9 - Nov 10
Total with taxes and fees
Hamilton Goebel House 816 E Louisa St Darlington Wi
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

8. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$179 nightly
The price is $203
Nov 15 - Nov 16
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

9. King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
$204 nightly
The price is $232
Nov 15 - Nov 16
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A wooden deck overlooking a calm river with trees and a building in the background.

10. Spacious 3-bedroom apartment in Downtown Stoughton

Spacious 3-bedroom apartment in Downtown Stoughton
Stoughton
10.0 out of 10, Exceptional, (1 review)
"The stay was very clean and comfortable. Location was super convenient—you’re right downtown surrounded by cute shops and restaurants. Grayson was so communicative and was such a responsive and accommodating host. Will absolutely return if we ever find ourselves needing to stay in Stoughton again. Highly recommend!"
United States
Laura M.
$334 nightly
The price is $379
Nov 30 - Dec 1
Total with taxes and fees
Spacious 3-bedroom apartment in Downtown Stoughton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Monticello Hotel Reviews

An indoor swimming pool with a wooden ceiling, tiled walls, and a clear view of the outdoors through a window.
Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI
Monroe

10/10 Excellent

The beds were very comfortable. The room was clean. The staff very pleasant.
United States
Tami
Reviewed April 29, 2025
Super 8 by Wyndham Monroe WI

Find out more about Monticello

Everything you need to know about Monticello vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monticello vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monticello vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Monticello vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monticello. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Monticello in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Monticello rentals

At Expedia, we put the best Monticello vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Monticello rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monticello vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monticello. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Monticello?

Yes, there are vacation rentals close to well known local attractions in Monticello, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Monticello?

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe: Visitors give good reviews to this Monticello vacation home rental, which is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Monticello?

Explore the area and family-friendly sights such as Swissland Miniature Golf, or get out into nature at a spot like Yellowstone Lake State Park. New Glarus Woods State Park and New Glarus Brewing Company are a couple of places you'll find in the larger area.

What are vacation rentals like in Monticello?

Vacation rentals are privately owned properties you can reserve for several days or longer in Monticello. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip or a small group gathering.