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Compare 117 Vacation Homes in Middleton with updated reviews, rates, and availability.

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (224)
"Our recent stay in Sun Prairie was wonderful. Randy and Connie are outstanding hosts. They greeted us when we arrived. Showed us all the features of the home and were available to answer any questions. They suggested places to take our grandchildren. The house was conveniently located to everything we wanted to do in Sun Prairie and is a short drive to Madison. Our grand daughter told us she wants to come back and stay in this our again."
The price is AED 826
AED 1,062 total
includes taxes & fees
2 Feb - 3 Feb
A Pleasant Retreat- No Cleaning Fee & New Discounts

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

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

10.0 out of 10, Exceptional, (103)
"enjoyable relaxing great place"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

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

9.8 out of 10, Exceptional, (31)
"Jake’s place was perfect for our stay, as it was a relaxing, clean and a nice home. The two floor layout worked especially well for our infant daughter so she had a quiet place to sleep, while we could cook and hang out in the living room. The only suggestion to the host is to install curtains along the picturesque sliding doors for a bit of extra privacy at nighttime."
The price is AED 974
AED 1,952 total
includes taxes & fees
17 Feb - 18 Feb
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Amazing townhouse, amazing attractions, amazing city!

10.0 out of 10, Exceptional, (161)
"The place was nice and clean. Perfect place for a book weekend!"
Amazing townhouse, amazing attractions, amazing city!

Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME

3.2 out of 10, (10)
"Fished the Madison chain while we stayed here. 20 minutes to the ramp. Plenty of places to eat in neighborhood easy gas stops on easy to ramp. Plenty of room to move around in house for the four of us. Driveway and street parking were available for two bass boats and trucks. Electric hook up was great for charging batteries."
The price is AED 544
AED 882 total
includes taxes & fees
7 Feb - 8 Feb
Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME

Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!

9.0 out of 10, Wonderful, (14)
"Fourteen of us came from out of town for an extended family Christmas in Lodi. The space was perfect for us all. Our 6 grandkids enjoyed spending time together over the weekend in their "community bedroom" and all adults had their own private space. We had plenty of space to spend time together in the living room, dining room, and kitchen. Everything was clean and cozy. Christmas decor was a nice touch! House was perfect!!"
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!

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

10.0 out of 10, Exceptional, (14)
"Supper clean, comfortable beds and great location. Will definitely stay here again. "
The price is AED 1,025
AED 1,323 total
includes taxes & fees
9 Feb - 10 Feb
Two bedroom suite with city views in the heart of downtown Madison

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (133)
"The cabin was absolutely spotless and well equipped. The owner was an excellent communicator - we did it all by email. The expectations for maintaining and checking out were very reasonable. I recommend this stay to anyone!"
ONE OF A KIND vacation rental with a view

Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

10.0 out of 10, Exceptional, (145)
"We traveled with our teen sons and dog for skiing and a basketball game. The location was convenient for all our plans. We all had plenty of space in this comfortable and clean home. "
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

Okee Bay House on Lake Wisconsin w/ Private Dock!

2.0 star property
10.0 out of 10, Exceptional, (3)
"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!

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!

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great stay, easy location."
The price is AED 804
AED 1,043 total
includes taxes & fees
3 Feb - 4 Feb
One Bedroom King with Den with views of the heart of downtown.

On the Yahara River, access to Madison Lakes

10.0 out of 10, Exceptional, (26)
"A must stay if you’re in the Madison area. "
On the Yahara River, access to Madison Lakes

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

9.0 out of 10, Wonderful, (4)
"Was in town for UWM parents weekend and wanted something more than a simple hotel room as I was going to be there for nearly a week. The Saddlery for the bill. Location was amazing. Having a kitchenette meant I could fully enjoy the great farmers market that weekend. And the view out my window of the lake was a perfect way to wake up. Manager was very responsive. Everything was as stated. TV/media set up would benefit from updating, but it actually didn’t matter as it allowed me to tuck into a...
The price is AED 584
AED 752 total
includes taxes & fees
3 Feb - 4 Feb
Studio queen with views of Lake Monona in the heart of downtown Madison

Lake Monona Waterfront + HOT TUB + Game Room

9.6 out of 10, Exceptional, (29)
"We had a great time in our trip. House was clean with a bunch of entertainment and near plenty of things to do. Owner was super responsive and accommodating. Thanks again!"
Lake Monona Waterfront + HOT TUB + Game Room

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

10.0 out of 10, Exceptional, (83)
"My college friends and I had the most lovely time at this cozy cabin! Everything was as mentioned in the description, the lake and views were stunning. We hiked nearby and happened upon the outdoor market in Baraboo. Saturday night dinner at Fish Tales just down the road was excellent. Highly recommended, will be back next year!"
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (31)
"Short uber to everything. Really my only complaint is the parking situation is inconvenient. And Madison parking rules are a little odd. Some of our group got parking tickets. May be worth notifying future guests so they can prepare or follow the rules accordingly. "
Doty ★ Walk to Everything -Hotel Quality- Downtown

Luxurious Country Retreat

10.0 out of 10, Exceptional, (8)
"The property was great for a large group. Plenty of beds, baths, and spaces for everyone to use."
Luxurious Country Retreat

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

10.0 out of 10, Exceptional, (39)
"This place is absolutely beautiful ! The property you stay on is an amazing farm. Trees everywhere, a pond, hills, cliffs. The home you rent is so homey, extremely clean,and these people have thought of everything to make it great for their guests. Tons of things to do during bad weather. The place is equiped with art supplies, games, movies - whatever you may like. The owner/property manager is the sweetest person ever, and always great to deal with. This has become our new favorite...
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.
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Other property types in Middleton

Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

10.0 out of 10, Exceptional, (145)
"We traveled with our teen sons and dog for skiing and a basketball game. The location was convenient for all our plans. We all had plenty of space in this comfortable and clean home. "
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

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

10.0 out of 10, Exceptional, (13)
"Everything is organized perfectly. Much thought has been put into making sure that guests are fully accommodated and comfortable. Beautiful extra touches left that show great consideration from the hosts! "
Elegant Space–Premium Kitchen–Spacious & Ideal for Gathering w/ Friends & Family

The Dylin by Locale

4.0 star property
10.0 out of 10, Exceptional, (2)
The price is AED 300
AED 346 total
includes taxes & fees
5 Feb - 6 Feb
The Dylin by Locale
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.