Monticello Holiday Rentals

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Holiday Rentals in Monticello

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

10.0 out of 10, Exceptional, (155)
"A comfy home in a quiet location, perfect for our weekend getaway. We've stayed here once before and would definitely come back again if it's available next time we're in the area. "
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, (364)
"Great host, super clean, beautiful!"
Nature Lover's Paradise In The Driftless Area Of Southern Wisconsin, USA.

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

9.6 out of 10, Exceptional, (64)
"A great place for a reunion of friends. Beautiful location with nearby trails. Host was excellent!!"
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Pool with Slide. Great for Business Travelers!

The price is NZ$325
includes taxes & fees
9 Oct - 10 Oct
Pool with Slide. Great for Business Travelers!

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (143)
"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

Enjoy Nature with Full Comfort!

9.2 out of 10, Wonderful, (32)
"Beautiful, comfortable and convenient. Couldn’t have been more pleased with our stay. "
The price is NZ$219
includes taxes & fees
7 Oct - 8 Oct
Enjoy Nature with Full Comfort!

Hamilton Goebel House 816 E Louisa St Darlington Wi

9.8 out of 10, Exceptional, (43)
"This was a wonderful property. The hosts were so accommodating and helpful. We had a great time."
The price is NZ$389
includes taxes & fees
7 Oct - 8 Oct
Hamilton Goebel House 816 E Louisa St Darlington Wi

Madison Area 3BR | Near Hiking Trails

10.0 out of 10, Exceptional, (14)
"Visited Madison for the first time and found this amazing house that had everything we needed to make our stay memorable "
The price is NZ$1,308
includes taxes & fees
7 Oct - 8 Oct
Madison Area 3BR | Near Hiking Trails

One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly

10.0 out of 10, Exceptional, (55)
"Our second visit, and we enjoyed it just as much! The property is outstanding, and the host is great - we will be back. Very highly recommended."
One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly

Winter Special w/Indoor Parking in Unique New Glarus, see details below.

10.0 out of 10, Exceptional, (5)
"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 NZ$1,093
includes taxes & fees
19 Oct - 20 Oct
Winter Special w/Indoor Parking in Unique New Glarus, see details below.

Paoli Den - Renovated Flat!

9.8 out of 10, Exceptional, (28)
"Prefect"
Paoli Den - Renovated Flat!

Luxurious Country Retreat

10.0 out of 10, Exceptional, (13)
"Amazing house both inside and outside. Would definitely stay here again. "
Luxurious Country Retreat

Legacy Guest House , Mount Horeb WI

10.0 out of 10, Exceptional, (64)
"This place worked great for my family to stay close to a wedding venue just outside of town."
Legacy Guest House , Mount Horeb WI

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

10.0 out of 10, Exceptional, (15)
"We had a nice time here. Easy to get in and out. Very accommodating and clean! Pretty cool place to stay in! "
The price is NZ$318
includes taxes & fees
7 Oct - 8 Oct
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

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

The price is NZ$368
includes taxes & fees
9 Oct - 10 Oct
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Beautiful two story, downtown home, one block from the Square,

10.0 out of 10, Exceptional, (34)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
The price is NZ$496
includes taxes & fees
8 Oct - 9 Oct
Beautiful two story, downtown home, one block from the Square,

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

10.0 out of 10, Exceptional, (97)
"In town for girls getaway. This was our second stay at this location. Everything about the stay was perfect will definitely be back! Myron and Jane are great hosts. 10/10!!"
The price is NZ$466
includes taxes & fees
8 Oct - 9 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square

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

9.2 out of 10, Wonderful, (5)
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.

Spacious 5-bedroom house sleeps 14 with pool, hot tub, sauna and more!

10.0 out of 10, Exceptional, (2)
"Perfect location for a family get together. Away from the hustle bustle, but close enough to restaurants and stores. House is clean, spacious and the pool is well maintained."
Spacious 5-bedroom house sleeps 14 with pool, hot tub, sauna and more!

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

9.8 out of 10, Exceptional, (30)
"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.
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 favorite 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 depends 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 NZ$318 per night. Entering your travel dates in the search wizard you might find 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.