Middleton Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Middleton holiday rentals

An outdoor patio with a brick grill and seating area.

1. King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.4 out of 10, Very good, (7 reviews)
"Great place for a stay."
United States
Andy D.
The price is NZ$328
includes taxes & fees
22 Nov - 23 Nov
King Suite | Free Breakfast. Pool and Hot Tub
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

2. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (217 reviews)
"Good location"
United States
ANCA
The price is NZ$220
includes taxes & fees
15 Dec - 16 Dec
The Dylin
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

3. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (59 reviews)
"Enjoyed the county setting and seeing the cranes and hearing the rooster crow!"
United States
Elizabeth C.
The price is NZ$225
includes taxes & fees
7 Dec - 8 Dec
A Room with a View
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

4. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is NZ$374
includes taxes & fees
16 Nov - 17 Nov
Pool with Slide. Great for Business Travelers!
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

5. The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
9.8 out of 10, Exceptional, (34 reviews)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
The price is NZ$420
includes taxes & fees
22 Nov - 23 Nov
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

6. King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
The price is NZ$428
includes taxes & fees
16 Nov - 17 Nov
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

7. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is NZ$437
includes taxes & fees
19 Nov - 20 Nov
Studio Apartment at Cannery Square
A modern living room with a sofa, coffee table, and dining area.

8. Historic Luxury 2-bedroom apartment in Cross Plains, WI

Historic Luxury 2-bedroom apartment in Cross Plains, WI
Cross Plains
The price is NZ$704
includes taxes & fees
15 Nov - 16 Nov
Historic Luxury 2-bedroom apartment in Cross Plains, WI
A modern living room with a flat-screen TV, leather seating, a ceiling fan, and large windows.

9. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (56 reviews)
"Great and easy stay! The place was comfortable and inviting. Would stay again!"
United States
Taylor S.
The price is NZ$592
includes taxes & fees
2 Dec - 3 Dec
2 Bed, 2 Bath Apartment at Cannery Square
A modern room with a kitchenette, a bed, a sofa, and a TV.

10. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.6 out of 10, Excellent, (17 reviews)
"Great location - able to walk to many stores and restaurants. Spacious for a studio and very quiet."
United States
Martha T.
The price is NZ$471
includes taxes & fees
15 Nov - 16 Nov
Studio Apartment at Cannery Square
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

11. Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (28 reviews)
"Amazing location, nicely furnished and cozy!"
United States
Heather & Nick V.
The price is NZ$466
includes taxes & fees
1 Dec - 2 Dec
Charming Downtown Two Bedroom w/ Fireplace
A modern kitchen with a dishwasher, a dining area with a table and chairs, a living room with a sofa and a TV, and a ceiling fan.

12. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (31 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is NZ$607
includes taxes & fees
16 Nov - 17 Nov
2 Bed, 2 Bath Apartment at Cannery Square
An outdoor seating area with wicker furniture and a central fire feature.

13. Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Madison
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and convenient! Everything went smooth."
United States
Thomas C.
The price is NZ$447
includes taxes & fees
29 Nov - 30 Nov
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

14. Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two
Dane
10.0 out of 10, Exceptional, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is NZ$476
includes taxes & fees
18 Nov - 19 Nov
Escape to tranquility – your countryside haven, and at times with a horse or two
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

15. Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (48 reviews)
"Great stay! Very close to everything downtown."
United States
Garrett M.
The price is NZ$544
includes taxes & fees
16 Nov - 17 Nov
Doty ★ Walk to Everything -Hotel Quality- Downtown
An outdoor seating area with wicker furniture and a central fire feature.

16. Accessible 1BR Suite | Free Daily Breakfast & Pool

Accessible 1BR Suite | Free Daily Breakfast & Pool
Madison
The price is NZ$443
includes taxes & fees
29 Nov - 30 Nov
Accessible 1BR Suite | Free Daily Breakfast & Pool
A modern kitchen with a refrigerator, microwave, and bar stools.

17. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (43 reviews)
"The host was very responsive and very kind and considerate to our reason for traveling. The property was beautiful and clean inside and out, we really enjoyed our stay."
United States
Sha'Vonne G.
The price is NZ$688
includes taxes & fees
17 Nov - 18 Nov
2 Bedroom Apartment Downtown Sun Prairie!
A spacious dining area with a high ceiling and large windows, wooden furniture, and a view of the outdoors.

18. Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (32 reviews)
"Great Place Beautiful landscape from the deckHost was very responsive Would go back again in a heartbeat Everything you need for a great stay"
United States
John W.
The price is NZ$736
includes taxes & fees
15 Nov - 16 Nov
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

19. Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (20 reviews)
"Everything was very nice"
United States
Anonymous traveller
The price is NZ$760
includes taxes & fees
16 Nov - 17 Nov
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A modern kitchen with a central island, dining area with a round table, and a visible refrigerator.

20. Charming 3-bedroom house on Madison's Eastside! Close to everything!

Charming 3-bedroom house on Madison's Eastside! Close to everything!
Madison
The price is NZ$1,036
includes taxes & fees
18 Nov - 19 Nov
Charming 3-bedroom house on Madison's Eastside! Close to everything!
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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Find holiday rentals that suit your style

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Top Middleton Hotel Reviews

A modern hotel with a glass facade, multiple floors, and a prominent entrance.
Embassy Suites By Hilton Madison Downtown

Embassy Suites By Hilton Madison Downtown

Embassy Suites By Hilton Madison Downtown
Downtown Madison

10/10 Excellent

Beautiful
Australia
Brad
Reviewed August 11, 2026
Embassy Suites By Hilton Madison Downtown

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$219 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?

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail: This holiday home rental outside of Middleton is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease 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. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Pheasant Branch Conservancy.

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.