Middleton Holiday Rentals

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Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Middleton holiday rentals

Smart TV, computer monitors
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Apartment in Middleton

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
2.0 star property
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.
The price is HK$1,113
HK$2,356 total
includes taxes & fees
4 Jan - 5 Jan 2026
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Outdoor pool, a heated pool
Contemporary home in quiet neighborhood with pool & great back yard close to all

Holiday Home in Middleton

Contemporary home in quiet neighborhood with pool & great back yard close to all
9.6 out of 10, Exceptional, (10)
"We were in town for an Ironman race. The property is perfect, lots of room, pool, great backyard. Neighborhood is quiet and safe. We walked and biked alot in neighborhood. And the Host is fantastic! If I could give more stars I would."
United States
Randall W.
Contemporary home in quiet neighborhood with pool & great back yard close to all
Interior entrance
The Dylin by Mint House

Aparthotel in Tenney-Lapham

The Dylin by Mint House
4.0 star property
9.4 out of 10, Exceptional, (121)
"Great location and very comfortable stay. Love the extra space to hang out."
United States
Brian
The price is HK$816
HK$943 total
includes taxes & fees
23 Dec - 24 Dec
The Dylin by Mint House
Free WiFi, bed sheets
Lake Wisconsin Resort

Cottage in Poynette

Lake Wisconsin Resort
3.0 star property
10.0 out of 10, Exceptional, (1)
"The cabins looked small from the outside, but we're actually very spacious we didn't feel cramped everything was very clean there was a full kitchen a table big enough to sit at least four. I think the only thing that wasn't 100% perfect was the beds are a little small they were stiff and the pillows were also very small and serviceable. I would still definitely stay there again 100% and would recommend it to everyone!"
United States
Shelley
Lake Wisconsin Resort
Exterior detail
A Pleasant Retreat- No Cleaning Fee & New Discounts

Holiday Home in Sun Prairie

A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (260)
"A great stay! A wonderful location and excellent property, along with kind and warm hosts. Thank you. "
United States
Rachel Z.
The price is HK$2,139
HK$2,757 total
includes taxes & fees
1 Jan - 2 Jan 2026
A Pleasant Retreat- No Cleaning Fee & New Discounts
Outdoor spa tub
Quietwater Cottage-Hot Tub, Nearby Skiing, Peaceful, Scenic, Birds, Nature!

Cottage in Poynette

Quietwater Cottage-Hot Tub, Nearby Skiing, Peaceful, Scenic, Birds, Nature!
9.8 out of 10, Exceptional, (252)
"This was a nice place to stay that was away from hustle of the city. It was beautiful outside and the cabin was cute and cozy."
United States
Pauley A.
Quietwater Cottage-Hot Tub, Nearby Skiing, Peaceful, Scenic, Birds, Nature!
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Capital PrimeTime - 6 Miles from Madison w/ fireplace

Condo in Sun Prairie

Capital PrimeTime - 6 Miles from Madison w/ fireplace
9.8 out of 10, Exceptional, (31)
"Everything about our experience staying here was excellent! Communication, very clean, nicely decorated, and in a great neighborhood with amenities close by."
United States
Nancy R.
The price is HK$2,917
HK$4,884 total
includes taxes & fees
12 Dec - 13 Dec
Capital PrimeTime - 6 Miles from Madison w/ fireplace
Outdoor spa tub
Island View Hideaway- Hot Tub, Nearby Skiing, Peaceful, Scenic, Birds, Nature!

Cottage in Poynette

Island View Hideaway- Hot Tub, Nearby Skiing, Peaceful, Scenic, Birds, Nature!
9.8 out of 10, Exceptional, (213)
"Wonderful cottage with everything we needed for a great stay. Loved watching the hummingbirds."
United States
Scott B.
Island View Hideaway- Hot Tub, Nearby Skiing, Peaceful, Scenic, Birds, Nature!
Smart TV, fireplace, DVD player, books
Conveniently Located just off University Avenue on Madison's West Side

Holiday Home in Spring Harbor

Conveniently Located just off University Avenue on Madison's West Side
10.0 out of 10, Exceptional, (131)
"It was great!"
United States
Guitar string S.
Conveniently Located just off University Avenue on Madison's West Side
Exterior
ONE OF A KIND vacation rental with a view

Holiday Home in Madison

ONE OF A KIND vacation rental with a view
10.0 out of 10, Exceptional, (147)
"This is a unique home that is super clean and had everything needed to cook, entertain (we played games & watched football) and accommodate any family. The location was close to downtown, the interstate, and airport. Plenty of restaurants were nearby as well. We thoroughly enjoyed our stay and would absolutely stay again. "
United States
Connie C.
ONE OF A KIND vacation rental with a view
Smart TV, fireplace, DVD player, books
Rocky Glen Condo - forest nest on Baraboo bluff

Condo in Merrimac

Rocky Glen Condo - forest nest on Baraboo bluff
10.0 out of 10, Exceptional, (336)
"Great comfortable space for our family. The host was very responsive, even mailed back our electric toothbrush we left behind. Would stay there again! "
United States
Kelly
Rocky Glen Condo - forest nest on Baraboo bluff
Outdoor dining
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

Holiday Home in Arena

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
9.8 out of 10, Exceptional, (7)
"Perfect spot for a family getaway"
United States
Steve M.
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
Dining
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Cabin in Merrimac

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
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.
The price is HK$1,225
HK$2,917 total
includes taxes & fees
14 Dec - 15 Dec
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Pool
Private Pool - HOT TUB - Sauna - Game Room - Pets

Holiday Home in Sun Prairie

Private Pool - HOT TUB - Sauna - Game Room - Pets
10.0 out of 10, Exceptional, (6)
"The house is great and the facilities in the house were well-functioning, and the dish washer saved us much time. The neighborhood is quiet and great views. We enjoyed our stay."
United States
Patti M.
Private Pool - HOT TUB - Sauna - Game Room - Pets
Interior
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Holiday Home in Verona

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
9.6 out of 10, Exceptional, (69)
"Beautiful location, nice spacious and clean spot. We had a great time. "
United States
Sarah B.
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
Terrace/patio
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Holiday Home in Faircrest

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
10.0 out of 10, Exceptional, (120)
"Scenic property, super zen, lovely hosts!"
United States
Christina C.
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Lobby
Pool with Slide. Great for Business Travelers!

Apartment in Fitchburg

Pool with Slide. Great for Business Travelers!
The price is HK$965
HK$1,266 total
includes taxes & fees
14 Dec - 15 Dec
Pool with Slide. Great for Business Travelers!
Smart TV
Doty ★ Walk to Everything -Hotel Quality- Downtown

Holiday Home in Downtown Madison

Doty ★ Walk to Everything -Hotel Quality- Downtown
9.8 out of 10, Exceptional, (36)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
United States
Mindi Z.
The price is HK$1,323
HK$2,229 total
includes taxes & fees
14 Dec - 15 Dec
Doty ★ Walk to Everything -Hotel Quality- Downtown
Property grounds
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Holiday Home in Arena

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
9.6 out of 10, Exceptional, (22)
"Barn was beautiful, clean & fun amenities."
United States
Kerry S.
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Terrace/patio
Free Breakfast Pool & Hot Tub. Near UW-Madison

Condo in Madison

Free Breakfast Pool & Hot Tub. Near UW-Madison
10.0 out of 10, Exceptional, (1)
"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."
United States
Joy E.
The price is HK$1,747
HK$2,314 total
includes taxes & fees
14 Dec - 15 Dec
Free Breakfast Pool & Hot Tub. Near UW-Madison
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

Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

10/10 Excellent
" Rooms were great ! Breakfast was awesome."
Jason 1-night trip
Posted 2 days ago
Hampton Inn & Suites Madison-West

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
  • Use the map to find apartments and other holiday homes in the Middleton neighbourhood you prefer
  • 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?

A Pleasant Retreat- No Cleaning Fee & New Discounts: This holiday home rental outside of Middleton offers a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Middleton?

Choose from 5 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 Pleasant View Golf Course and Capital Brewery.

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.