Middleton Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Middleton holiday rentals

Terrace/patio

King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (5 reviews)
"Great place for a stay."
United States
Andy D.
The price is HK$768
HK$1,064 total
includes taxes & fees
19 Apr - 20 Apr
King Suite | Free Breakfast. Pool and Hot Tub
Smart TV, computer monitors

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, (2 reviews)
"This stay was truly perfect! Our hosts thought of every single detail and more. The property was perfectly appointed with all the little touches that made it ideal for a quiet couple's getaway just outside Madison. We drove nearly 8 hours north from Kansas City to get here, so imagine how wonderful it was to walk into a warm, cozy, welcoming house that had snacks on hand and a pizza delivery number front and center waiting for us! Best part of all - it was dog-friendly! Our dog immediately felt...
United States
Heather P.
The price is HK$1,050
HK$1,818 total
includes taxes & fees
23 Apr - 24 Apr
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Fridge, microwave, oven, stovetop

2 Bedroom - Main Street Sun Prairie WI

2 Bedroom - Main Street Sun Prairie WI
Sun Prairie
9.6 out of 10, Exceptional, (40 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 HK$1,512
HK$3,164 total
includes taxes & fees
19 Apr - 20 Apr
2 Bedroom - Main Street Sun Prairie WI
Lobby

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 HK$1,223
HK$1,587 total
includes taxes & fees
11 May - 12 May
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Interior

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Sun Prairie
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful spacious property, extremely clean and excellent host!"
United States
Jen F.
The price is HK$2,585
HK$4,415 total
includes taxes & fees
16 Apr - 17 Apr
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
1 bedroom, iron/ironing board, free WiFi, bed sheets

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
10.0 out of 10, Exceptional, (22 reviews)
"A very unique place in a fantastic location! Little touches made our stay wonderful."
United States
Mike L.
The price is HK$1,018
HK$1,760 total
includes taxes & fees
20 Apr - 21 Apr
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Exterior

Cannery Square Short Term Rentals -102 by Patriot

Cannery Square Short Term Rentals -102 by Patriot
Sun Prairie
8.0 out of 10, Very good, (12 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
The price is HK$908
HK$2,150 total
includes taxes & fees
16 Apr - 17 Apr
Cannery Square Short Term Rentals -102 by Patriot
Interior

Updated home with lake views, across the street from Lake Wisc!

Updated home with lake views, across the street from Lake Wisc!
Merrimac
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful home, Merrimack is such a quaint town. "
United States
Laura L.
The price is HK$1,058
HK$2,221 total
includes taxes & fees
20 Apr - 21 Apr
Updated home with lake views, across the street from Lake Wisc!
Dining

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful house! We loved the basement game room and found our stay very comfortable. "
United States
Anonymous traveller
The price is HK$1,421
HK$3,207 total
includes taxes & fees
20 Apr - 21 Apr
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Exterior

Cannery Square Unit - 106 by Patriot Properties

Cannery Square Unit - 106 by Patriot Properties
Sun Prairie
9.4 out of 10, Exceptional, (28 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is HK$1,230
HK$2,803 total
includes taxes & fees
11 May - 12 May
Cannery Square Unit - 106 by Patriot Properties
Smart TV, fireplace, stereo, printers

Spring Escape Near UW

Spring Escape Near UW
Fitchburg
10.0 out of 10, Exceptional, (21 reviews)
"We enjoyed staying here. VERY nice house, easy access, clean, a lot of space, no issues. We would book here again!"
United States
Liz A.
The price is HK$2,657
HK$6,465 total
includes taxes & fees
21 Apr - 22 Apr
Spring Escape Near UW
Property grounds

Waters Edge Cottage

Waters Edge Cottage
Merrimac
7.8 out of 10, Good, (12 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
The price is HK$1,943
HK$4,010 total
includes taxes & fees
19 Apr - 20 Apr
Waters Edge Cottage
Reception

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (134 reviews)
"Well-decorated, coffee/kitchenette setup was great! "
United States
Chandra
The price is HK$969
HK$1,119 total
includes taxes & fees
19 Apr - 20 Apr
The Dylin
Smart TV

Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful host, and a beautiful home within walking distance to many restaurants and museums. Parking nearby was easy to find. We were able to rest and relax, and make many meals there. Great kitchen amenities, and very comfortable beds. Truly a warm and inviting home. I would highly recommend!"
United States
Jacquie T.
The price is HK$1,332
HK$2,271 total
includes taxes & fees
19 Apr - 20 Apr
Doty ★ Walk to Everything -Hotel Quality- Downtown
Outdoor dining

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (39 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
The price is HK$705
HK$1,074 total
includes taxes & fees
6 May - 7 May
Enjoy Nature with Full Comfort!
Exterior

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Monona
9.8 out of 10, Exceptional, (51 reviews)
"It was lovely to be by the lake and have the view from the living room along with gas fireplace. So relaxing even in the off season."
United States
Justine K.
The price is HK$1,869
HK$3,926 total
includes taxes & fees
19 Apr - 20 Apr
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Lobby

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is HK$1,089
HK$1,408 total
includes taxes & fees
19 Apr - 20 Apr
Pool with Slide. Great for Business Travelers!
Dining

Lodge w/ Indoor Pool along Devil's Lake Park!

Lodge w/ Indoor Pool along Devil's Lake Park!
Merrimac
10.0 out of 10, Exceptional, (6 reviews)
"Great for large groups! Beautiful, secluded property with lots of amenities!"
United States
Bronson S.
The price is HK$7,383
HK$13,941 total
includes taxes & fees
22 Apr - 23 Apr
Lodge w/ Indoor Pool along Devil's Lake Park!
Exterior

Cannery Square Short Term Rentals -307 by Patriot

Cannery Square Short Term Rentals -307 by Patriot
Sun Prairie
The price is HK$776
HK$1,839 total
includes taxes & fees
21 Apr - 22 Apr
Cannery Square Short Term Rentals -307 by Patriot
Terrace/patio

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cozy Cabin on Crooked Lane close to Lake Wisconsin
Poynette
10.0 out of 10, Exceptional, (1 review)
"Pet friendly cabin in the woods. Mostly updated and nice for 4-6 people. We stayed with our dogs and it worked well for us. "
United States
Jon A.
The price is HK$1,198
HK$2,156 total
includes taxes & fees
16 Apr - 17 Apr
Cozy Cabin on Crooked Lane close to Lake Wisconsin
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

DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

10/10 Excellent
"Breakfast menu was delicious, staff was warm and accomodating."
Jessica 2-night trip
Posted 4 hours ago
DoubleTree by Hilton Madison East

Find out more about Middleton

Search for holiday rentals in Middleton on Expedia! You can easily find your home rentals, villas, holiday apartments in Middleton using one of the methods below:

  • View our selection of featured holiday rentals in Middleton
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  • Enter your travel dates to view the best deals on holiday rentals in Middleton while they last

Look no further and take a look at our great range of rental properties in Middleton!

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?

Private Pool - Hot Tub - Game Room - 20 min DT: This holiday home rental outside of Middleton offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 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 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.