Monticello Holiday Rentals

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Holiday Rentals in Monticello

Our top choices for Monticello holiday rentals

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

10.0 out of 10, Exceptional, (152)
"Fantastic area to explore"
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe

Nature Lover's Paradise In The Driftless Area Of Southern Wisconsin, USA.

10.0 out of 10, Exceptional, (360)
"Great host, super clean, beautiful!"
Nature Lover's Paradise In The Driftless Area Of Southern Wisconsin, USA.

The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.

8.8 out of 10, Excellent, (3)
"Quiet and peaceful. Close to Apple River Canyon and Yellowstone State Park. My wife and I had a wonderful time. Our dog had a blast too. We are planning on returning."
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.

Paoli Den - Renovated Flat!

9.8 out of 10, Exceptional, (25)
"Prefect"
Paoli Den - Renovated Flat!

Pool with Slide. Great for Business Travelers!

The price is AU$284
includes taxes & fees
11 Sept - 12 Sept
Pool with Slide. Great for Business Travelers!

Enjoy Nature with Full Comfort!

9.4 out of 10, Exceptional, (30)
"Great location, beautiful, clean, and friendly host"
The price is AU$198
includes taxes & fees
14 Sept - 15 Sept
Enjoy Nature with Full Comfort!

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

10.0 out of 10, Exceptional, (15)
"I had the pleasure of spending a short weekend at The Earthhouse BnB in Mt. Horeb, and it was absolutely wonderful! The property is tucked away in a serene, peaceful location that provided the perfect escape from the hustle and bustle of everyday life. The BnB itself is charming and cozy, with unique touches that made it feel like a true home away from home."
The price is AU$286
includes taxes & fees
9 Sept - 10 Sept
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (142)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view

Beautifully updated home close to downtown New Glarus

10.0 out of 10, Exceptional, (59)
"Nice home, good neighborhood. Host easy to reach and very helpful."
Beautifully updated home close to downtown New Glarus

Destination Driftless- A Trailside Retreat

9.4 out of 10, Exceptional, (29)
"Great place to stay. We werent at the house much. Just to sleep and get ready. House decor is very cute."
Destination Driftless- A Trailside Retreat

99.00 Fall Special in beautiful New Glarus

10.0 out of 10, Exceptional, (3)
"LOVELY PLACE! 3 comfy beds, nice bathrooms, living toom & large dining table easily accommodated our group. The kitchen was well stocked for us to prepare our meals. Great location, easy walking around the fun town!!"
The price is AU$909
includes taxes & fees
9 Sept - 10 Sept
99.00 Fall Special in beautiful New Glarus

Luxurious Country Retreat

10.0 out of 10, Exceptional, (13)
"Luxurious and spacious house on a large and beautiful piece of land. Was equipped with everything we could want. We had a wonderful time and would absolutely stay here again. "
Luxurious Country Retreat

Hamilton Goebel House 816 E Louisa St Darlington Wi

9.8 out of 10, Exceptional, (42)
"Will definitely stay again!"
The price is AU$349
includes taxes & fees
9 Sept - 10 Sept
Hamilton Goebel House 816 E Louisa St Darlington Wi

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (64)
"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Historic Country Farmhouse for ANY Season!

10.0 out of 10, Exceptional, (45)
"Great weekend with girls. Host was very attentive. Location was great, close to shopping and wineries."
Historic Country Farmhouse for ANY Season!

Sugar River Suite - Your Sweet Escape in the Heart of it All!

10.0 out of 10, Exceptional, (18)
"Great place for a getaway! This was clean, downtown, close to everything and perfect. "
Sugar River Suite - Your Sweet Escape in the Heart of it All!

Look out at the treetops at the cozy Paoli Nest. Near Epic Systems and Madison.

9.8 out of 10, Exceptional, (28)
"Had a great stay for a few days while our son played in Madison. The home was clean, easy to get to and the hosts were amazing!!"
Look out at the treetops at the cozy Paoli Nest. Near Epic Systems and Madison.

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

10.0 out of 10, Exceptional, (96)
"Had a great stay for St Pats Parade!"
The price is AU$406
includes taxes & fees
10 Sept - 11 Sept
MJ's Penthouse ,a piece of paradise on Monroe's historic square

KC HOUSE Cozy Country Home. Enjoy the country life!

10.0 out of 10, Exceptional, (16)
"More than we expected! We were so comfortable and loved every minute being there. We will definitely be back! "
KC HOUSE Cozy Country Home. Enjoy the country life!

3BR/3BA Home | Dual Living Spaces

10.0 out of 10, Exceptional, (12)
"Beautiful furnishings, very clean, Well stocked. Would definitely stay there again. The host was very responsive."
The price is AU$1,223
includes taxes & fees
9 Sept - 10 Sept
3BR/3BA Home | Dual Living Spaces
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

Find out more about Monticello

Find out more about Monticello

Everything you need to know about Monticello holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Monticello holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Monticello holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monticello holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Monticello holiday rentals we have selected for you start as low as AU$198 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Monticello rentals

At Expedia, we put the best Monticello holiday 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 holiday.

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 holiday rentals in Monticello?

Yes, there are holiday rentals close to the most popular sights in Monticello, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Monticello has to offer?

3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe: This highly rated holiday home rental in Monticello is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday 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 New Glarus Woods State Park Trailhead. New Glarus Woods State Park and New Glarus Brewing Company are a couple of places you'll find in the wider area.

What are holiday rentals like in Monticello?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Monticello. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a family trip.