Middleton Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Middleton holiday rentals

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, (6 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$1,051
HK$1,802 total
includes taxes & fees
1 Jun - 2 Jun
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
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$1,034
HK$1,357 total
includes taxes & fees
4 Jun - 5 Jun
King Suite | Free Breakfast. Pool and Hot Tub
Outdoor dining

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (43 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
The price is HK$741
HK$1,112 total
includes taxes & fees
11 Jun - 12 Jun
Enjoy Nature with Full Comfort!
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
9.8 out of 10, Exceptional, (26 reviews)
"A very unique place in a fantastic location! Little touches made our stay wonderful."
United States
Mike L.
The price is HK$980
HK$1,841 total
includes taxes & fees
1 Jun - 2 Jun
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Exterior

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
The price is HK$776
HK$1,830 total
includes taxes & fees
1 Jun - 2 Jun
Studio Apartment at Cannery Square
Exterior

2 Bed/ 2 Bath At Cannery Square

2 Bed/ 2 Bath At Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (50 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
2 Bed/ 2 Bath At Cannery Square
Exterior

2 Bed/ 2 Bath At Cannery Square

2 Bed/ 2 Bath At Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (28 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
2 Bed/ 2 Bath At Cannery Square
Terrace/patio

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cozy Cabin on Crooked Lane close to Lake Wisconsin
Poynette
8.0 out of 10, Very good, (2 reviews)
"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$1,399
HK$2,394 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Cabin on Crooked Lane close to Lake Wisconsin
TV, fireplace, table football, offices

Hot Tub - King Suite - Game Room - Large Groups

Hot Tub - King Suite - Game Room - Large Groups
Sun Prairie
10.0 out of 10, Exceptional, (19 reviews)
"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"
United States
George P.
The price is HK$1,669
HK$5,283 total
includes taxes & fees
2 Jun - 3 Jun
Hot Tub - King Suite - Game Room - Large Groups
Fridge, microwave, oven, stovetop

2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
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$3,156 total
includes taxes & fees
15 Jun - 16 Jun
2 Bedroom Apartment Downtown Sun Prairie!
Fridge, microwave, oven, stovetop

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

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (13 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is HK$1,204
HK$3,697 total
includes taxes & fees
2 Jun - 3 Jun
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
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)
"We were looking for a peaceful getaway and place to unwind distress and relax… Speaking with Brittany was quick and easy, we knew that this was the place for us. Booking was easy and the directions to get there were a breeze… The property is beautiful in the home was everything we hoped it would be and more."
United States
Ryan F.
The price is HK$1,871
HK$3,760 total
includes taxes & fees
1 Jun - 2 Jun
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Outdoor dining

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
The price is HK$1,089
HK$1,862 total
includes taxes & fees
11 Jun - 12 Jun
Escape to tranquility – your countryside haven, and at times with a horse or two
Lobby

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is HK$1,106
HK$1,427 total
includes taxes & fees
28 Jun - 29 Jun
Pool with Slide. Great for Business Travelers!
Exterior

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (13 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
The price is HK$909
HK$2,169 total
includes taxes & fees
1 Jun - 2 Jun
Studio Apartment at Cannery Square
Reception

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (145 reviews)
"nice location"
United States
Mary
The price is HK$963
HK$1,112 total
includes taxes & fees
1 Jun - 2 Jun
The Dylin
Property grounds

Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.0 out of 10, Very good, (13 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
The price is HK$1,943
HK$4,011 total
includes taxes & fees
1 Jun - 2 Jun
Waters Edge Cottage
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$1,265
HK$1,634 total
includes taxes & fees
4 Jun - 5 Jun
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Outdoor spa tub

Private Pool - Hot Tub - Game Room - 20 min DT

Private Pool - Hot Tub - Game Room - 20 min DT
Sun Prairie
10.0 out of 10, Exceptional, (4 reviews)
"We had a great family weekend in a great home that had plenty of space for all 12 of us. It was clean and the host was very accommodating and responsive. We will definitely look to stay there again on our next ski adventure. "
United States
Kylie V.
The price is HK$3,127
HK$7,782 total
includes taxes & fees
3 Jun - 4 Jun
Private Pool - Hot Tub - Game Room - 20 min DT
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, (52 reviews)
"The location is wonderful. The river setting is beautiful. The pelicans are so fun to watch. Enjoyed all the rooms with tvs."
United States
Robert
The price is HK$1,942
HK$4,028 total
includes taxes & fees
2 Jun - 3 Jun
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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
"Always a great experience"
Tracy 3-night trip
Posted 1 hour ago
The Madison Concourse Hotel and Governor's Club

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?

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 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 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 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.