Holiday Rentals in Middleton

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Middleton

Contemporary home in quiet neighborhood with pool & great back yard close to all

9.6 out of 10, Exceptional, (8)
"Everything was just as advertised. The backyard & stay was very enjoyable. Thank you for a lovely stay, Sheila!"
Contemporary home in quiet neighborhood with pool & great back yard close to all

The Dylin

4.0 star property
9.2 out of 10, Wonderful, (72)
"Nice place very cozy"
The Dylin

Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME

3.2 out of 10, (10)
"Couldnt even sleep there the place smelled like straight cat pee and had real feces present horrible cant believe they allow this place to stay on VRBO"
The price is €210
includes taxes & fees
4 Jul - 5 Jul
Big House, Nice neighborhood, PET FAMILY FRIENDLY HOME

Rocky Glen Condo - forest nest on Baraboo bluff

10.0 out of 10, Exceptional, (324)
"Beautiful place! Loved everything about it! Excellent hostess! "
Rocky Glen Condo - forest nest on Baraboo bluff

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (28)
"Supper clean, comfortable beds and great location. Will definitely stay here again. "
The price is €400
includes taxes & fees
7 Jul - 8 Jul
Two bedroom suite with city views in the heart of downtown Madison

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.6 out of 10, Exceptional, (20)
"What a great spot right on the lake and near a lot of great restaurants and places. "
The price is €343
includes taxes & fees
6 Jul - 7 Jul
One Bedroom King with Den with views of Lake Monona in the heart of downtown.

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect

2.0 out of 10, (1)
"Host never showed up to let us in the property and still has not reimbursed me "
Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (57)
"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

9.8 out of 10, Exceptional, (238)
"Cozy cabin, nestled in the outskirts of Baraboo. Great for the scenery and hiking. A chance to unplug and get away from the big city to spend quality time nature. "
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

Country Sportsmans Paradise!! Grill, Firepit & AC - Devil's Lake and Dells area!

10.0 out of 10, Exceptional, (2)
"Beautiful home, convenient location. The taxidermy was fascinating, and it had a lovely secret room. "
Country Sportsmans Paradise!! Grill, Firepit & AC - Devil's Lake and Dells area!

Spacious 5-bedroom 80 acres family farm retreat with AC, WiFi in rural Verona

10.0 out of 10, Exceptional, (1)
"The house was clean, spacious, and filled with light, with lots of windows looking out on acres of woods and hay and corn fields. Located on a dead end road, there was no traffic noise and no lights visible at night. We enjoyed hiking on the Ice Age Trail nearby, biking on the Badger State Trail, swimming at the Verona High School Aquatic Center. and picking strawberries, as well as going into Madison for some great Thai food. This is a perfect house for a family, with lots of room for kids to...
Spacious 5-bedroom 80 acres family farm retreat with AC, WiFi in rural Verona

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (138)
"It was a very nice place. Clean, spacious, unique and quiet. Very good communication, quick response from host whenever I had questions. We definitely recommend this place and love to stay again if we have a chance. "
ONE OF A KIND vacation rental with a view

Madison & ~UW~-Madison Area Lakefront Home

10.0 out of 10, Exceptional, (191)
"We had a wonderful weekend here with family. A beautiful place to stay with gorgeous views of the lake. The house was super clean and felt like home. We cannot wait to go back again! Jennifer was amazing!"
Madison & ~UW~-Madison Area Lakefront Home

Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!

9.8 out of 10, Exceptional, (202)
"Very clean nice place with a wonderful hot tub, and amazing views."
Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!

Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!

9.8 out of 10, Exceptional, (85)
"This was a great place to stay for a weekend getaway with some friends. Would love to come by again in the summer time "
Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!

Spacious & Modern Home w/ Deck in Oregon!

10.0 out of 10, Exceptional, (1)
"Awesome...very clean property.Plenty of space for eight people...Quiet neighborhood"
Spacious & Modern Home w/ Deck in Oregon!

Studio queen with views of Lake Monona in the heart of downtown Madison

9.4 out of 10, Exceptional, (8)
"We had no issues with our stay and really enjoyed the unit we booked. "
Studio queen with views of Lake Monona in the heart of downtown Madison

Two Bedroom with views of Lake Monona in the heart of downtown Madison

10.0 out of 10, Exceptional, (5)
"We loved everything about this property. Would definitely stay there again."
The price is €423
includes taxes & fees
6 Jul - 7 Jul
Two Bedroom with views of Lake Monona in the heart of downtown Madison

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (19)
"Everything we needed easy commute to city of wisconson, clean, great communication with the host and the host left a welcome basket for us that was focused towards the reason we were in town, world championship strongman competition. "
Paoli Den - Newly Remodeled!

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (241)
"Very comfortable and clean. 2 adults and 2 children had plenty of room to play and relax Location was easy to get to and easy to get around to places we wanted to visit in Madison "
A Pleasant Retreat- No Cleaning Fee & New Discounts
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

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?

One Bedroom King with Den with views of Lake Monona in the heart of downtown.: This holiday home rental outside of Middleton is in the city centre and offers cable TV to help you feel perfectly comfortable in your new surroundings.

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 Pleasant View Golf Course.

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.