Holiday Homes in Monticello

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
26 Sept - 28 Sept
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

Featured Holiday Homes in Monticello

Our top choices for Monticello holiday homes

Paoli Den - Renovated Flat!
Fridge, microwave, oven, stovetop

Paoli Den - Renovated Flat!

9.8 out of 10, Exceptional, (26)
"Prefect"
Paoli Den - Renovated Flat!
Nature Lover's Paradise In The Driftless Area Of Southern Wisconsin, USA.
Smart TV, fireplace, video games, DVD player

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.
Exterior

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

9.0 out of 10, Wonderful, (4)
"We loved our stay. This property was just as described, on a quiet dead end road. There were lots of towels and GREAT pillows. This was our ATV trip and this property is just a few blocks away from the ATV trail. We enjoyed watching the cows as they watched us. We will stay again."
The Windmill on Slough Rd. 2 bedroom 1.5 bath on quiet dead end road.
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Exterior

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 NZ$310
includes taxes & fees
30 Sept - 1 Oct
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Beautifully updated home close to downtown New Glarus
Exterior detail

Beautifully updated home close to downtown New Glarus

10.0 out of 10, Exceptional, (60)
"Nice home, good neighborhood. Host easy to reach and very helpful."
Beautifully updated home close to downtown New Glarus
Destination Driftless- A Trailside Retreat
Interior

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
ONE OF A KIND vacation rental with a view
Exterior

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
Hamilton Goebel House 816 E Louisa St Darlington Wi
Fridge, microwave, oven, stovetop

Hamilton Goebel House 816 E Louisa St Darlington Wi

9.8 out of 10, Exceptional, (43)
"Will definitely stay again!"
The price is NZ$380
includes taxes & fees
18 Sept - 19 Sept
Hamilton Goebel House 816 E Louisa St Darlington Wi
Winter Special w/Indoor Parking in Unique New Glarus, see details below.
Fridge, microwave, oven, stovetop

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

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 NZ$956
includes taxes & fees
30 Sept - 1 Oct
Winter Special w/Indoor Parking in Unique New Glarus, see details below.
Beautifully remodeled 2 bed 104 Berkley Verona #6
Exterior

Beautifully remodeled 2 bed 104 Berkley Verona #6

9.6 out of 10, Exceptional, (24)
"The apartment is well maintained and Joel was helpful. We’d stay again if we need a place to stay in Verona"
Beautifully remodeled 2 bed 104 Berkley Verona #6
Historic Country Farmhouse for ANY Season!
Property grounds

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!
Darlington River View House - Direct Trail Access
Living area

Darlington River View House - Direct Trail Access

10.0 out of 10, Exceptional, (1)
"Everything was great!! House manager was very thorough, easy to contact and answered questions in a timely manner! The house was perfect for what we needed, house was clean and comfy! Would highly recommend to anyone wanting to stay in Darlington!"
Darlington River View House - Direct Trail Access
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
Smart TV, fireplace, video games, DVD player

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
Luxurious Country Retreat
Fridge, microwave, oven, stovetop

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

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 NZ$451
includes taxes & fees
22 Sept - 23 Sept
MJ's Penthouse ,a piece of paradise on Monroe's historic square
KC HOUSE Cozy Country Home. Enjoy the country life!
Exterior

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!
Fully decked out 4 Bdrm, relaxing backyard retreat. Minutes from Epic
Terrace/patio

Fully decked out 4 Bdrm, relaxing backyard retreat. Minutes from Epic

10.0 out of 10, Exceptional, (8)
"Host was very accommodating! Home is cozy and comfortable felt like home. Thank you again for opening your home and giving us a place to stay! "
Fully decked out 4 Bdrm, relaxing backyard retreat. Minutes from Epic
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
Exterior

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

10.0 out of 10, Exceptional, (153)
"Great location to roam around the southern area of Wisconsin"
3 Bedroom, 2 Bath House, Large Yard, 4 Miles From New Glarus, 10 Miles To Monroe
3BR/3BA Home | Dual Living Spaces
Fridge, microwave, oven, stovetop

3BR/3BA Home | Dual Living Spaces

10.0 out of 10, Exceptional, (13)
"Beautiful furnishings, very clean, Well stocked. Would definitely stay there again. The host was very responsive."
The price is NZ$1,310
includes taxes & fees
21 Sept - 22 Sept
3BR/3BA Home | Dual Living Spaces
One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly
TV, DVD player, books, video library

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

10.0 out of 10, Exceptional, (54)
"4th time here and it just gets better. The owners are so nice, and the house is clean and interesting. Will be back for a 5th visit soon!"
One-of-a-kind house on 240 acres w/ prairie, woods & trout-stream - pet-friendly
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Monticello Hotel Reviews

AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

10/10 Excellent
"Nice place, great breakfast "
Kristine 3-night trip
Posted 1 day ago
AmericInn by Wyndham Madison West

Find out more about Monticello

Find out more about Monticello

Monticello Holiday Homes information

Number of reviews
1,159
Accommodation
59 Holiday Homes
Lowest Price
NZ$310
Highest Price
NZ$1,310

Explore a world of travel with Expedia

Explore a world of travel with Expedia