Search Vacation Homes in Middleton

    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
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 146 Vacation Homes in Middleton with updated reviews, rates, and availability.

One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Aerial view

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.6 out of 10, Exceptional, (19)
"What a great spot right on the lake and near a lot of great restaurants and places. "
The price is AED 1,025
AED 1,353 total
includes taxes & fees
15 May - 16 May
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Amazing townhouse, amazing attractions, amazing city!
Fridge, microwave, oven, stovetop

Amazing townhouse, amazing attractions, amazing city!

10.0 out of 10, Exceptional, (168)
"The place was nice and clean. Perfect place for a book weekend!"
Amazing townhouse, amazing attractions, amazing city!
Two bedroom suite with city views in the heart of downtown Madison
Aerial view

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (26)
"Supper clean, comfortable beds and great location. Will definitely stay here again. "
The price is AED 1,208
AED 1,595 total
includes taxes & fees
15 May - 16 May
Two bedroom suite with city views in the heart of downtown Madison
One Bedroom King with Den with views of the heart of downtown.
Aerial view

One Bedroom King with Den with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great stay, easy location."
The price is AED 988
AED 1,307 total
includes taxes & fees
15 May - 16 May
One Bedroom King with Den with views of the heart of downtown.
A Pleasant Retreat- No Cleaning Fee & New Discounts
Exterior

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (233)
"Our 2nd stay at this home and it was perfection again. Well stocked with anything you could want and a true home away from home. Cannot imagine spending a week, with kids, in anything less. Already checking dates for our next trip north. "
A Pleasant Retreat- No Cleaning Fee & New Discounts
Paoli Den - Newly Remodeled!
Fridge, microwave, oven, stovetop

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (16)
"Everything we needed easy commute to city of wisconson, clean, great communication with the host and the host left a welcome basket for us that was focused towards the reason we were in town, world championship strongman competition. "
Paoli Den - Newly Remodeled!
Studio queen with views of Lake Monona in the heart of downtown Madison
Aerial view

Studio queen with views of Lake Monona in the heart of downtown Madison

9.2 out of 10, Wonderful, (7)
"We enjoyed our stay. Good location and view. Would stay here again."
The price is AED 768
AED 1,014 total
includes taxes & fees
15 May - 16 May
Studio queen with views of Lake Monona in the heart of downtown Madison
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Miscellaneous

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (34)
"We were looking forward convenient location in Madison to see family and this place was perfect!"
The price is AED 974
AED 1,977 total
includes taxes & fees
26 May - 27 May
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Legacy Guest House , Mount Horeb WI
Fridge, microwave, oven, stovetop

Legacy Guest House , Mount Horeb WI

10.0 out of 10, Exceptional, (56)
"This is a very cute place in a perfect location. We were blocks away from downtown with cute shops and restaurants. The kitchen was stocked with lots of spices and everything we needed to fix amazing meals. "
Legacy Guest House , Mount Horeb WI
On the Yahara River, access to Madison Lakes
TV, fireplace, stereo

On the Yahara River, access to Madison Lakes

10.0 out of 10, Exceptional, (30)
"A must stay if you’re in the Madison area. "
On the Yahara River, access to Madison Lakes
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Outdoor spa tub

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (110)
"enjoyable relaxing great place"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Fridge, microwave, oven, stovetop

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

10.0 out of 10, Exceptional, (2)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
The price is AED 551
AED 1,713 total
includes taxes & fees
12 May - 13 May
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.
Exterior

Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.

10.0 out of 10, Exceptional, (1)
"The Johnson house was perfect for our family of 5 and our golden doodle to stay for the Christmas holiday. We were in town visiting family and needed a place for all of us to stay. Stacy had even gone above and beyond and had a Christmas tree and decorations to truly make it feel like home. The house is in a great location to be able to visit our family members spread all around Dane County."
Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
Beach towels

Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path

10.0 out of 10, Exceptional, (33)
"Overall great"
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
Entire 3 Bedroom with Fireplace - sleeps 12
Terrace/patio

Entire 3 Bedroom with Fireplace - sleeps 12

9.6 out of 10, Exceptional, (10)
"Great place in Sun Prairie for 9 adult family members plus our dog to stay for two nights while attending a family wedding. Comfortable & large home. Great location in a very walkable neighborhood."
The price is AED 1,286
AED 2,215 total
includes taxes & fees
8 May - 9 May
Entire 3 Bedroom with Fireplace - sleeps 12
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Smart TV, fireplace

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME
Terrace/patio

Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME

3.2 out of 10, (10)
"Couldnt even sleep there the place smelled like straight cat pee and had real feces present horrible cant believe they allow this place to stay on VRBO"
The price is AED 544
AED 887 total
includes taxes & fees
8 May - 9 May
Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME
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, (136)
"Awesome stay with Son and Grandsons. Great place to stay."
ONE OF A KIND vacation rental with a view
Okee Bay House on Lake Wisconsin w/ Private Dock!
Fridge, microwave, stovetop, dishwasher

Okee Bay House on Lake Wisconsin w/ Private Dock!

2.0 star property
10.0 out of 10, Exceptional, (5)
"Visiting for the Lodi Curling Club's Men's Bonspiel, and the location was a short drive to the club and near a couple great restaurant/bars!"
Okee Bay House on Lake Wisconsin w/ Private Dock!
Spacious country retreat w/pool 10 minutes to downtown Madison! Pet friendly!
Outdoor dining

Spacious country retreat w/pool 10 minutes to downtown Madison! Pet friendly!

8.0 out of 10, Very Good, (7)
"Lovely property and spacious home with lots of good hangout areas. Fully stocked with anything u could need and nice decorations throughout"
Spacious country retreat w/pool 10 minutes to downtown Madison! 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.
Don't see what you're looking for?
See all available properties in Middleton
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middleton

Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family
Terrace/patio

Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family

10.0 out of 10, Exceptional, (13)
"Wonderful property and hosts. Everything was perfect."
Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family
The Dylin
Interior entrance

The Dylin

4.0 star property
9.2 out of 10, Wonderful, (42)
"Great stay"
The price is AED 372
AED 429 total
includes taxes & fees
18 May - 19 May
The Dylin
Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME
Terrace/patio

Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME

3.2 out of 10, (10)
"Couldnt even sleep there the place smelled like straight cat pee and had real feces present horrible cant believe they allow this place to stay on VRBO"
The price is AED 544
AED 887 total
includes taxes & fees
8 May - 9 May
Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME
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.