A calm body of water reflecting a sunset sky with scattered clouds.

Middleton Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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
8.0 out of 10, Very good, (6 reviews)
"Great place for a stay."
United States
Andy D.
The price is AU$255
includes taxes & fees
1 Nov - 2 Nov
King Suite | Free Breakfast. Pool and Hot Tub
A spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

2. Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place, great stay."
United States
Thomas D.
The price is AU$415
includes taxes & fees
25 Oct - 26 Oct
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

3. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (196 reviews)
"Good location"
United States
ANCA
The price is AU$204
includes taxes & fees
1 Nov - 2 Nov
The Dylin
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

4. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (56 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
The price is AU$182
includes taxes & fees
21 Oct - 22 Oct
A Room with a View
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

5. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is AU$299
includes taxes & fees
18 Oct - 19 Oct
Pool with Slide. Great for Business Travelers!
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

6. 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, (33 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 AU$366
includes taxes & fees
18 Oct - 19 Oct
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.

7. 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 AU$339
includes taxes & fees
18 Oct - 19 Oct
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

8. 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 AU$359
includes taxes & fees
18 Oct - 19 Oct
Escape to tranquility – your countryside haven, and at times with a horse or two
A modern living room with a sofa, coffee table, and dining area.

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

Historic Luxury 2-bedroom apartment in Cross Plains, WI
Cross Plains
The price is AU$586
includes taxes & fees
18 Oct - 19 Oct
Historic Luxury 2-bedroom apartment in Cross Plains, WI
A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

10. 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)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
The price is AU$500
includes taxes & fees
19 Oct - 20 Oct
2 Bed, 2 Bath Apartment at Cannery Square
Bright, open lobby seating area — a comfortable space to relax or catch up on work

11. 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.
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

12. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is AU$388
includes taxes & fees
1 Nov - 2 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.

13. 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 AU$397
includes taxes & fees
1 Nov - 2 Nov
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.

14. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (30 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is AU$500
includes taxes & fees
28 Oct - 29 Oct
2 Bed, 2 Bath Apartment at Cannery Square
A modern kitchen with a refrigerator, microwave, and bar stools.

15. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (41 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 AU$568
includes taxes & fees
18 Oct - 19 Oct
2 Bedroom Apartment Downtown Sun Prairie!
A kitchen with a sliding glass door leading to a wooden deck with a view of a grassy field and a lake.

16. Updated home with lake views, across the street from Lake WI, near free ferry

Updated home with lake views, across the street from Lake WI, near free ferry
Merrimac
10.0 out of 10, Exceptional, (48 reviews)
"Very clean property, exactly as advertised. Host was easy to work with."
United States
Jacob M.
The price is AU$472
includes taxes & fees
18 Oct - 19 Oct
Updated home with lake views, across the street from Lake WI, near free ferry
A gym with treadmills, elliptical machines, and free weights.

17. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very good, (16 reviews)
"Great little town to stay the night. Woke early 5:30 am to tow truck towing cars in front lot. We luckily parked in back lot as instructed. Other than the noise of this unfortunate event, we enjoyed our stay. Loved the town and many places to walk to. Pizza place was amazing!"
United States
Cheryl B.
The price is AU$398
includes taxes & fees
28 Oct - 29 Oct
Studio Apartment at Cannery Square
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
9.6 out of 10, Exceptional, (30 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 AU$538
includes taxes & fees
27 Oct - 28 Oct
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, (19 reviews)
"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 AU$638
includes taxes & fees
1 Nov - 2 Nov
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A cozy cabin interior with a wooden ceiling, a large window, a dining area, and a seating area with a chair and sofa.

20. COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SPRING AND SUMMER FUN !!

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SPRING AND SUMMER FUN !!
Lodi
10.0 out of 10, Exceptional, (114 reviews)
"Beautiful view! Nice features all around!"
United States
Tim
The price is AU$602
includes taxes & fees
29 Oct - 30 Oct
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SPRING AND SUMMER FUN !!
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

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"Clean rooms, attentive staff, fantastic Governers Club perks, and perfect location."
Davin 1-night trip
Posted 10 hours ago
The Madison Concourse Hotel and Governor's Club

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 favourite 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 depend 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 AU$182 per night. Entering your travel dates in the search wizard might find you 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.