Middleton Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Middleton

Outdoor dining
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
10.0 out of 10, Exceptional, (132)
"We loved our stay. The house was comfortable and clean. It had all the amenities. The location was spectacular, and the backyard was super peaceful. Joan was a great host and communication was easy. There are three bedrooms for six people and a full-size futon, which is great for our group of 6."
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
Interior
Rocky Glen Condo - forest nest on Baraboo bluff
10.0 out of 10, Exceptional, (304)
"Overall we had an amazing trip. The host was super friendly and the place was fantastic. She had thought of everything needed to make it a comfortable stay. I will definitely stay here again."
Rocky Glen Condo - forest nest on Baraboo bluff
Outdoor dining
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
10.0 out of 10, Exceptional, (36)
"We had a great time! House was so clean and stocked with everything we needed. Would definitely stay again. Just adorable! I would recommend cutting the grass and storing your wood in a sheltered area. The wood was too wet to use-we had to purchase some & the grass was long with prickly vines on the stairs. The grass was long around the BBQ."
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
Save an average of 15% on thousands of hotels when you're signed in
Fridge, microwave, oven, stovetop
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
9.8 out of 10, Exceptional, (60)
"It was a perfect house for our group and we had a great weekend enjoying everything it had to offer!"
The price is NZ$2,202
per night
26 May - 27 May
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
Fridge, microwave, oven, stovetop
Legacy Guest House , Mount Horeb WI
10.0 out of 10, Exceptional, (36)
"Nice place to stay"
Legacy Guest House , Mount Horeb WI
Fridge, microwave, oven, stovetop
Amazing townhouse, amazing attractions, amazing city!
10.0 out of 10, Exceptional, (136)
"We rented this place to visit family in Madison and attend a ren faire. It was great as we were looking for a small place with a full kitchen to cook. Neat touches with the Alexa with song and light recommendations. We enjoyed the living room white board - played lots of Pictionary. Our group was myself, my daughter, and my sister. The basement den made a great third bedroom. I might recommend a pull out couch."
Amazing townhouse, amazing attractions, amazing city!
Property grounds
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
10.0 out of 10, Exceptional, (80)
"Everything was absolutely great! Location was perfect, lots of good restaurants and shopping near the house. Beautiful scenery and tranquil setting for relaxing. House was just as advertised and had everything we needed. Hosts are amazing and so kind! You’ll love the visits from their pups! Highly recommend!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Fridge, microwave, oven, stovetop
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
10.0 out of 10, Exceptional, (4)
"Our family had a fantastic time! The host was flexible and generous, the accommodations beautiful, and the amenities unique and fun!"
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Property grounds
Enjoy Nature with Full Comfort!
9.8 out of 10, Exceptional, (10)
"Space is clean, property is very pretty! Pool wasn’t ready for use, but can imagine it would add even more to the a summer stay! Owner is easy to communicate with. Ran into severe weather - owners were welcoming and ensured we were safe at all times. We will definitely be back to visit again!"
The price is NZ$211
per night
28 May - 29 May
Enjoy Nature with Full Comfort!
Exterior
A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (187)
"This was our first experience renting this home & we're definitely booking this home again next year. Everything from very attentive, kind renters, too extremely clean & renovated home, extremely comfortable beds & pillows. Not to mention the gorgeous & relaxing back yard. Perfect place to stay, for sure"
A Pleasant Retreat- No Cleaning Fee & New Discounts
On the beach
Madison & ~UW~-Madison Area Lakefront Home
9.8 out of 10, Exceptional, (165)
"The cottage is clean and well stocked for a long weekend. The view of the lake is beautiful, and I'm sure it's even better in the warm months. We had everything we needed. Great little house for a long weekend."
Madison & ~UW~-Madison Area Lakefront Home
Property grounds
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
10.0 out of 10, Exceptional, (17)
"Our stay at the Pink Acorn was amazing! Kelly truly makes her guests feel welcome. She left a sweet note and lovely treats. The house is stocked with everything you need and was exceptionally clean. The beds are super comfortable and have nice cozy blankets. Am added bonus was seeing rabbits and chipmunks in the backyard. Kelly leaves directions to walk to the beach around the corner and it’s a must do…and make sure to grab some ice cream at the shop across from the park."
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
Fridge, microwave, oven, stovetop
Two bedroom suite with city views in the heart of downtown Madison
10.0 out of 10, Exceptional, (2)
"Great property. Highly recommend it!!!"
The price is NZ$951
per night
26 May - 27 May
Two bedroom suite with city views in the heart of downtown Madison
Lake
Quietwater Cottage- On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!
9.8 out of 10, Exceptional, (221)
"Welcoming cozy cottage. Excellent location for bird watching & near by hiking at state parks. Friendly neighborhood :)"
Quietwater Cottage- On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!
Property grounds
Newly renovated home close to downtown New Glarus
10.0 out of 10, Exceptional, (48)
"Property is a perfect place for a getaway. House is blocks from downtown and neighborhood is absolutely charming. Great amenities and all the comforts of home. Hosts were great with communication and recommendations. Beds are super comfortable. We will absolutely love to stay there again."
Newly renovated home close to downtown New Glarus
Fridge, microwave, oven, stovetop
Cozy, Spacious Downtown Verona 3 Bedroom Home
10.0 out of 10, Exceptional, (17)
"The property was clean, tidy and highly functional. 5 stars!"
Cozy, Spacious Downtown Verona 3 Bedroom Home
Fridge, microwave, oven, stovetop
Monona Home
10.0 out of 10, Exceptional, (19)
"Great property. Fenced in back yard great for dogs!"
Monona Home
5 bedrooms, free WiFi, bed sheets
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
9.0 out of 10, Wonderful, (7)
"There is more than enough beds for a group of 10 to have their own beds. The town is nice and quiet and it’s a 30 second walk to the nearest bar. We never felt on top of each other and were really comfortable in the house. I would go back!"
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
Fridge, microwave, oven, stovetop
Relax & Unwind in this full apartment w/ Most Attractions close by!
10.0 out of 10, Exceptional, (37)
"Great friend get away. Quiet, clean, and affordable."
The price is NZ$276
per night
28 May - 29 May
Relax & Unwind in this full apartment w/ Most Attractions close by!
Exterior
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
10.0 out of 10, Exceptional, (4)
"Our family enjoyed a delightful weekend stay at the EarthHouse for the graduation of our oldest son from UW. Pam wished us well from the onset & was extremely helpful when we added our middle son to our stay. At the time of booking, we were unaware that he would be able to join us for the graduation festivities. However, Pam accommodated our changing needs after arrival without creating any anxiety for us on our exciting weekend. We enjoyed a fantastic dinner in Mt Horeb Friday evening at Bistro...
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Don't see what you're looking for?
See all available properties in 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.

Other types of properties in Middleton you may be interested in

Lobby
Country Inn & Suites by Radisson, Madison West, WI
2.5 star property
8.8 out of 10, Excellent, (1002)
"Comfortable, clean and more breakfast then listed. "
The price is NZ$149
per night
9 Jun - 10 Jun
Country Inn & Suites by Radisson, Madison West, WI
Exterior
Fairfield Inn & Suites by Marriott Madison West/Middleton
2.5 star property
9.0 out of 10, Wonderful, (667)
"Nothing to change. Perfect!"
The price is NZ$139
per night
9 Jun - 10 Jun
Fairfield Inn & Suites by Marriott Madison West/Middleton
Exterior
Courtyard by Marriott Madison West Middleton
3.0 star property
9.0 out of 10, Wonderful, (942)
"Nice hotel located close to Middleton and only a short drive from Madison. Comfortable beds and nice common areas make this a good option. Also convenient if you are visiting Taliesin and other spots west of town."
The price is NZ$172
per night
9 Jun - 10 Jun
Courtyard 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middleton holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middleton. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middleton. Seeing all the best attractions is bound to make you fall in love with Middleton. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middleton short-term rentals, that won’t be hard to do.

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 Capital Brewery and Death's Door Spirits Distillery.

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.

Recent reviews of Middleton properties
Expedia verified reviews