Middleton Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

This weekend
Next weekend

Our top choices for Middleton vacation rentals

8.0 out of 10, Very Good, (5)
"Great place for a stay."
United States
Andy D.
$124 nightly
The price is $142
Jan 1 - Jan 2, 2026
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
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.
$274 nightly
The price is $303
Jan 4 - Jan 5, 2026
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
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.
$163 nightly
The price is $180
Jan 1 - Jan 2, 2026
Total with taxes and fees
Sugar River Suite - Your Sweet Escape in the Heart of it All!
9.4 out of 10, Exceptional, (26)
"Great place "
United States
Armando
$284 nightly
The price is $320
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cannery Square Unit - 106 by Patriot Properties
9.6 out of 10, Exceptional, (36)
"Clean and quiet. Nice neighborhood amenities. "
United States
Mark L.
$283 nightly
The price is $318
Jan 11 - Jan 12, 2026
Total with taxes and fees
2 Bedroom - Main Street Sun Prairie WI
9.8 out of 10, Exceptional, (46)
"Roomy. Kitchen had basics. Good beds and pillows. "
United States
Susan
$284 nightly
The price is $320
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cannery Square Short Term Rentals -104 by Patriot
10.0 out of 10, Exceptional, (19)
"Very clean and comfortable and a great location within walking distance to downtown."
United States
Holly
$186 nightly
The price is $211
Jan 3 - Jan 4, 2026
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
9.2 out of 10, Wonderful, (39)
"Clean room, nice host, good air conditioning, beautiful location."
United States
Michael S.
$121 nightly
The price is $128
Jan 1 - Jan 2, 2026
Total with taxes and fees
Enjoy Nature with Full Comfort!

Vacation 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.
$390 nightly
The price is $442
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
$143 nightly
The price is $161
Jan 1 - Jan 2, 2026
Total with taxes and fees
Pool with Slide. Great for Business Travelers!

Vacation 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.
$193 nightly
The price is $223
Jan 1 - Jan 2, 2026
Total with taxes and fees
Studio Queen in the heart of downtown.
$164 nightly
The price is $186
Jan 1 - Jan 2, 2026
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
10.0 out of 10, Exceptional, (264)
"Great place and the hosts were great!"
United States
Drew M.
$312 nightly
The price is $351
Jan 1 - Jan 2, 2026
Total with taxes and fees
A Pleasant Retreat- No Cleaning Fee & New Discounts
9.8 out of 10, Exceptional, (47)
"We had a great time on our weekend trip to Madison. Location was super quick to get to downtown, house was clean, and we really enjoyed taking the canoe out on the lakes to explore."
United States
Molly S.
$439 nightly
The price is $498
Jan 1 - Jan 2, 2026
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
9.8 out of 10, Exceptional, (37)
"The property itself was fantastic-clean and comfortable. The location was also very convenient in terms of access to downtown, the lake and so on. The neighborhood seemed to be a lot of college housing so there was some evening noise that quieted down by 10 or so. "
United States
Lily H.
$248 nightly
The price is $287
Jan 4 - Jan 5, 2026
Total with taxes and fees
Doty ★ Walk to Everything -Hotel Quality- Downtown

Apartment in Sun Prairie

1 Bedroom - 1220 Canterbury Ct
$251 nightly
The price is $282
Jan 1 - Jan 2, 2026
Total with taxes and fees
1 Bedroom - 1220 Canterbury Ct
2.0 star property
$247 nightly
The price is $286
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
10.0 out of 10, Exceptional, (13)
"Everything about this stay was absolutely wonderful. The host was very responsive. The decor was charming, the accommodations were just as described and exceptionally clean. Couldn't ask for a better host or stay."
United States
Brenda R.
$508 nightly
The price is $572
Jan 1 - Jan 2, 2026
Total with taxes and fees
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
9.8 out of 10, Exceptional, (21)
"Everything was exactly as listed and the property was so beautiful. Came with some friends and will definitely try to come back soon! "
United States
Paul G.
$413 nightly
The price is $446
Jan 21 - Jan 22, 2026
Total with taxes and fees
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
9.8 out of 10, Exceptional, (15)
"Plenty of blankets pillows bed were great"
United States
Kimberly P.
$528 nightly
The price is $594
Jan 4 - Jan 5, 2026
Total with taxes and fees
Entire 3 Bedroom with Fireplace - sleeps 12
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middleton Hotel Reviews

Find out more about Middleton

Everything you need to know about Middleton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middleton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middleton vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middleton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $142 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middleton rentals

At Expedia, we put the best Middleton vacation 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 vacation.

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 vacation rental in Middleton?

Yes, we offer vacation rentals close to popular points of interest in Middleton, or you can go with a more secluded option if you want a relaxing place to stay. Tourists like the array of shops and top-notch restaurants in Middleton. Make sure you have time to check out the cafes and football games during your trip.

What's the top vacation rental that Middleton has to offer?

A Pleasant Retreat- No Cleaning Fee & New Discounts: Visitors like this Middleton vacation home rental. It offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Middleton?

Choose from 4 Expedia vacation rentals in Middleton for a memorable vacation.

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 vacation rental in Middleton like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Middleton. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for families.