Middleton Holiday Rentals

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Holiday Rentals in Middleton

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

10.0 out of 10, Exceptional, (146)
"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

4.0 star property
9.8 out of 10, Exceptional, (23)
"Beautifully decorated, extremely clean, very comfortable bed."
The price is AU$170
includes taxes & fees
12 Mar - 13 Mar
The Dylin

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 AU$387
includes taxes & fees
12 Mar - 13 Mar
Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME

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

9.6 out of 10, Exceptional, (15)
"Everything but said it would be"
The price is AU$488
includes taxes & fees
12 Mar - 13 Mar
One Bedroom King with Den with views of Lake Monona in the heart of downtown.

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

10.0 out of 10, Exceptional, (17)
"Barn was beautiful, clean & fun amenities."
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Quietwater Cottage- Scenic, On the Water, Nature&Birds, Peaceful, Nearby Skiing!

9.8 out of 10, Exceptional, (234)
"Cozy cabin, nestled in the outskirts of Baraboo. Great for the scenery and hiking. A chance to unplug and get away from the big city to spend quality time nature. "
Quietwater Cottage- Scenic, On the Water, Nature&Birds, Peaceful, Nearby Skiing!

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

2.0 star property
10.0 out of 10, Exceptional, (7)
"Nice loft style units in a great part of town. We had a great experience"
The price is AU$467
includes taxes & fees
12 Mar - 13 Mar
One Bedroom King with Den with views of the heart of downtown.

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

9.8 out of 10, Exceptional, (18)
"Great place to stay. Good location that was easy to walk to multiple bars and restaurants. Would highly recommend this apartment!"
The price is AU$594
includes taxes & fees
12 Mar - 13 Mar
Two bedroom suite with city views in the heart of downtown Madison

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (227)
"The property was perfect for our day of visiting with our friends we had not seen in three years. The accommodations were cozy and comfortable. The amenities met our needs offering a warm atmosphere and areas to have appetizers and play games. The sleeping accommodations were comfortable and spacious. The location provided plenty of options for restaurants for dining. We will definitely think of this property for a return friendship reunion in the future. "
The price is AU$466
includes taxes & fees
19 Mar - 20 Mar
A Pleasant Retreat- No Cleaning Fee & New Discounts

Island View Hideaway - Peaceful, Waterfront, Scenic, Nature, Nearby Skiing!

9.8 out of 10, Exceptional, (194)
"It was a comfortable visit. We enjoyed the Christmas decorations and the hot tub. It was very convenient to have two bathrooms, and to be able to bring our dog with us."
Island View Hideaway - Peaceful, Waterfront, Scenic, Nature, Nearby Skiing!

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (11)
"First, the owner Michelle was very responsive to every inquiry. The house was clean and comfortable. She even left us snacks and treats and a handwritten note. We had a wonderful stay. "
Paoli Den - Newly Remodeled!

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

9.8 out of 10, Exceptional, (33)
"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 AU$867
includes taxes & fees
12 Mar - 13 Mar
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

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

Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!

9.8 out of 10, Exceptional, (82)
"This was a great place to stay for a weekend getaway with some friends. Would love to come by again in the summer time "
Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!

Cozy 3 Bedroom Cottage- Breathtaking Lake Views

9.2 out of 10, Wonderful, (13)
"Great location. We enjoyed our stay and had many laughs. The bugs and bees in the kitchen along with the toaster and microwave that sometimes worked added to the funny memories. "
The price is AU$531
includes taxes & fees
12 Mar - 13 Mar
Cozy 3 Bedroom Cottage- Breathtaking Lake Views

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

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

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

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 AU$339
includes taxes & fees
12 Mar - 13 Mar
Studio queen with views of Lake Monona in the heart of downtown Madison

Enjoy Nature with Full Comfort!

9.6 out of 10, Exceptional, (25)
"Perfect size and location for visiting friends and family. The view of the valley is delightful. The unit is attached to the main house but has its own entrance. Clean and comfortable, the room was a bit like a private hotel room in the country. It's a short drive to Verona, Mt. Horeb or to Madison. I brought my dog, who loved the large yard and visiting the nearby dog park. "
The price is AU$222
includes taxes & fees
12 Mar - 13 Mar
Enjoy Nature with Full Comfort!
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 types of properties in Middleton you may be interested in

Country Inn & Suites by Radisson, Madison West, WI

2.5 star property
8.8 out of 10, Excellent, (1001)
"There were a lot of loud people staying there and I found a dirty washcloth in the shower. There was never anyone at the front desk but otherwise it was fine."
The price is AU$137
includes taxes & fees
13 Mar - 14 Mar
Country Inn & Suites by Radisson, Madison West, WI

Courtyard by Marriott Madison West Middleton

3.0 star property
9.0 out of 10, Wonderful, (1001)
"It was clean and quiet."
The price is AU$152
includes taxes & fees
16 Mar - 17 Mar
Courtyard by Marriott Madison West Middleton

Residence Inn by Marriott Madison West/Middleton

3.0 star property
9.2 out of 10, Wonderful, (499)
"We had a wonderful time at your hotel! All I would wish for is better quality Kleenex, and better quality toilet paper.Both felt like gas station quality. "
The price is AU$156
includes taxes & fees
16 Mar - 17 Mar
Residence Inn by Marriott Madison West/Middleton
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.

Frequently asked questions

Can I find a holiday rental in Middleton?

Yes, there are holiday rentals close to the most popular sights in Middleton, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Middleton. Make sure you have time to check out the cafés and football games during your trip.

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

Two bedroom suite with city views in the heart of downtown Madison: This holiday home rental outside of Middleton is on a lake, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Middleton?

Choose from 5 Expedia holiday rentals in Middleton for a memorable holiday.

What’s there to see and do in Middleton?

Cultural attractions include National Mustard Museum, whereas Lake Mendota is a spot to enjoy nature. Other places in town to visit include Capital Brewery and Pleasant View Golf Course.

What’s a holiday rental in Middleton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleton. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family gatherings.