Middleton Holiday Rentals

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Our top choices for Middleton holiday rentals

10.0 out of 10, Exceptional, (2)
"We had a fantastic stay at this property, and it truly exceeded our expectations. The location is excellent—perfectly situated with convenient access to both the east and west sides of Madison, making it easy to get wherever we needed to go. The owners were incredibly helpful and responsive, answering the few questions we had quickly and kindly, which made the entire experience even smoother.One of the biggest highlights for us was the private fenced-in area, which was absolutely perfect for our...
United States
Jessi P.
The price is NZ$519
includes taxes & fees
6 Jan - 7 Jan 2026
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
8.0 out of 10, Very good, (5)
"Great place for a stay."
United States
Andy D.
The price is NZ$243
includes taxes & fees
30 Dec - 31 Dec
King Suite | Free Breakfast. Pool and Hot Tub

Holiday Home in Village of Cottage Grove

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
10.0 out of 10, Exceptional, (7)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
The price is NZ$776
includes taxes & fees
11 Jan - 12 Jan 2026
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
10.0 out of 10, Exceptional, (20)
"Super clean & right in the middle of town. Great place for a girls getaway weekend!"
United States
Rachel I.
The price is NZ$352
includes taxes & fees
30 Dec - 31 Dec
Sugar River Suite - Your Sweet Escape in the Heart of it All!

Aparthotel in Tenney-Lapham

The Dylin by Mint House
4.0 star property
9.4 out of 10, Exceptional, (122)
"Great stay at the Dylin"
United States
Lauri
The price is NZ$228
includes taxes & fees
29 Dec - 30 Dec
The Dylin by Mint House
10.0 out of 10, Exceptional, (19)
"Very clean and comfortable and a great location within walking distance to downtown."
United States
Holly
The price is NZ$331
includes taxes & fees
28 Dec - 29 Dec
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
9.6 out of 10, Exceptional, (36)
"Clean and quiet. Nice neighborhood amenities. "
United States
Mark L.
The price is NZ$537
includes taxes & fees
11 Jan - 12 Jan 2026
2 Bedroom - Main Street Sun Prairie WI
9.6 out of 10, Exceptional, (44)
"Roomy. Kitchen had basics. Good beds and pillows. "
United States
Susan
The price is NZ$547
includes taxes & fees
11 Jan - 12 Jan 2026
Cannery Square Short Term Rentals -104 by Patriot
9.2 out of 10, Wonderful, (39)
"Well-appointed, very clean space on a stunning property! Easy check-in. Everything we needed. Good communication with the host. We hope to return!"
United States
Thea S.
The price is NZ$219
includes taxes & fees
28 Dec - 29 Dec
Enjoy Nature with Full Comfort!
10.0 out of 10, Exceptional, (13)
"Everything was great !"
United States
Beth V.
The price is NZ$979
includes taxes & fees
28 Dec - 29 Dec
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
9.4 out of 10, Exceptional, (26)
"Great place "
United States
Armando
The price is NZ$547
includes taxes & fees
30 Dec - 31 Dec
Cannery Square Unit - 106 by Patriot Properties
2.0 star property
10.0 out of 10, Exceptional, (1)
"The house was clean, large, and nicely decorated. It felt welcoming and homey. The host was friendly and responsive to our questions. "
United States
Ellen M.
The price is NZ$1,352
includes taxes & fees
28 Dec - 29 Dec
Hot Tub - Private Pool - Game Room - 20 min DT

Holiday Home in Downtown Madison

Studio Queen in the heart of downtown.
2.0 star property
10.0 out of 10, Exceptional, (1)
"Convenient location for events on the Capital Square, State Street and UW-Madison Campus."
United States
Jeffrey W.
The price is NZ$382
includes taxes & fees
28 Dec - 29 Dec
Studio Queen in the heart of downtown.
10.0 out of 10, Exceptional, (16)
"We had a great visit "
United States
Jennifer D.
The price is NZ$1,154
includes taxes & fees
28 Dec - 29 Dec
Hot Tub - King Suite - Game Room - Large Groups
9.8 out of 10, Exceptional, (32)
"Everything about our experience staying here was excellent! Communication, very clean, nicely decorated, and in a great neighborhood with amenities close by."
United States
Nancy R.
The price is NZ$1,076
includes taxes & fees
1 Jan - 2 Jan 2026
Capital PrimeTime - 6 Miles from Madison w/ fireplace
The price is NZ$276
includes taxes & fees
1 Jan - 2 Jan 2026
Pool with Slide. Great for Business Travelers!
10.0 out of 10, Exceptional, (7)
"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!!"
United States
Brooke
The price is NZ$1,176
includes taxes & fees
17 Jan - 18 Jan 2026
“Steps into Little Switzerland” Indoor Parking at The Belvedere.
2.0 star property
The price is NZ$501
includes taxes & fees
28 Dec - 29 Dec
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
10.0 out of 10, Exceptional, (31)
"Beautiful home, Merrimack is such a quaint town. "
United States
Laura L.
Updated home near ski hills, lake views and across the street from Lake Wisc!
2.0 star property
The price is NZ$1,122
includes taxes & fees
28 Dec - 29 Dec
Hot Tub - Game Room - 20 min to Downtown - Pets
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 Middleton Hotel Reviews

Find out more about Middleton

Everything you need to know about Middleton 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 Middleton 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 Middleton holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middleton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middleton. 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 Middleton 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 Middleton holiday rentals we have selected for you start as low as NZ$228 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middleton rentals

At Expedia, we put the best Middleton 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 Middleton 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 Middleton 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 Middleton. 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 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?

A Pleasant Retreat- No Cleaning Fee & New Discounts: This holiday home rental outside of Middleton offers a patio, a garden and a BBQ to help you feel perfectly comfortable 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 and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Middleton?

Choose from 4 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 Pleasant View Golf Course and Capital Brewery.

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.