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Middleton Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Middleton vacation rentals

An outdoor patio with a brick grill and seating area.

1. King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (6 reviews)
"Great place for a stay."
United States
Andy D.
The price is ￥21,340
￥28,083 total
includes taxes & fees
Oct 4 - Oct 5
King Suite | Free Breakfast. Pool and Hot Tub
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

2. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (188 reviews)
"The Dylan was a great location for us and we were very pleased with the garage parking, new modern finishes and the communication of the host. The unit had everything we needed for a super comfortable stay including a full kitchen and washer/dryer. No wasted space. Good arrangement in this two bedroom unit for 2 couples. Would stay here again and recommend."
United States
Debbie
The price is ￥18,402
￥21,254 total
includes taxes & fees
Oct 25 - Oct 26
The Dylin
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

3. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (54 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
The price is ￥12,173
￥19,480 total
includes taxes & fees
Sep 29 - Sep 30
A Room with a View
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

4. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is ￥23,553
￥30,303 total
includes taxes & fees
Oct 4 - Oct 5
Pool with Slide. Great for Business Travelers!
A spacious living room with a fireplace, comfortable seating, and a television mounted above it.

5. 3BR/3BA Home | Dual Living Spaces

3BR/3BA Home | Dual Living Spaces
Fitchburg
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful place with lots of room. "
United States
Brenda B.
The price is ￥43,994
￥111,521 total
includes taxes & fees
Sep 27 - Sep 28
3BR/3BA Home | Dual Living Spaces
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

6. 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 ￥28,295
￥35,686 total
includes taxes & fees
Oct 26 - Oct 27
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A modern living room with a sofa, coffee table, and dining area.

7. Historic Luxury 2-bedroom apartment in Cross Plains, WI

Historic Luxury 2-bedroom apartment in Cross Plains, WI
Cross Plains
The price is ￥35,388
￥62,124 total
includes taxes & fees
Sep 27 - Sep 28
Historic Luxury 2-bedroom apartment in Cross Plains, WI
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

8. 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, (31 reviews)
"A very unique place in a fantastic location! Little touches made our stay wonderful."
United States
Mike L.
The price is ￥20,446
￥38,381 total
includes taxes & fees
Oct 1 - Oct 2
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
An outdoor seating area with wicker furniture and a central fire feature.

9. Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Madison
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and convenient! Everything went smooth."
United States
Thomas C.
The price is ￥31,456
￥39,965 total
includes taxes & fees
Oct 4 - Oct 5
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

10. 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
10.0 out of 10, Exceptional, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is ￥23,277
￥37,887 total
includes taxes & fees
Oct 11 - Oct 12
Escape to tranquility – your countryside haven, and at times with a horse or two
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

11. Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (45 reviews)
"Great place!"
United States
Robert F.
The price is ￥60,081
￥83,382 total
includes taxes & fees
Oct 8 - Oct 9
Doty ★ Walk to Everything -Hotel Quality- Downtown
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

12. 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, (56 reviews)
"Great little lake house, close to downtown Madison. "
United States
LiHsin C.
The price is ￥39,561
￥76,143 total
includes taxes & fees
Oct 8 - Oct 9
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
A chalkboard sign with a welcome message and room instructions.

13. 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, (23 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
The price is ￥55,048
￥88,824 total
includes taxes & fees
Sep 29 - Sep 30
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
A modern kitchen with a dishwasher, a dining area with a table and chairs, a living room with a sofa and a TV, and a ceiling fan.

14. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (30 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is ￥19,975
￥52,552 total
includes taxes & fees
Oct 4 - Oct 5
2 Bed, 2 Bath Apartment at Cannery Square
A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

15. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (55 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
The price is ￥19,975
￥52,552 total
includes taxes & fees
Oct 19 - Oct 20
2 Bed, 2 Bath Apartment at Cannery Square
A modern kitchen with a refrigerator, microwave, and bar stools.

16. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (41 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 ￥30,355
￥59,985 total
includes taxes & fees
Oct 4 - Oct 5
2 Bedroom Apartment Downtown Sun Prairie!
A bedroom with a dark grey wall, a bed with a striped bedspread, multiple pillows, a small side table with a vase and a lamp, and two framed botanical prints on the wall.

17. Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
10.0 out of 10, Exceptional, (56 reviews)
"Great, comfortable stay. And close to shopping, which is just what I like to do! "
United States
Joyana A.
The price is ￥63,227
￥99,972 total
includes taxes & fees
Sep 27 - Sep 28
Capital City- 6 Miles from Madison with fireplace
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

18. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is ￥12,740
￥40,211 total
includes taxes & fees
Oct 4 - Oct 5
Studio Apartment at Cannery Square
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

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

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (19 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is ￥24,913
￥70,048 total
includes taxes & fees
Oct 26 - Oct 27
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A hotel room with a bed, a desk, a lamp, a framed picture, a kitchen area with cabinets and a microwave, and a carpeted floor.

20. Free Breakfast Pool & Hot Tub. Near East Towne Mall!

Free Breakfast Pool & Hot Tub. Near East Towne Mall!
Madison
10.0 out of 10, Exceptional, (1 review)
"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 ￥51,745
￥64,384 total
includes taxes & fees
Oct 4 - Oct 5
Free Breakfast Pool & Hot Tub. Near East Towne Mall!
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
"Great location and classic upscale hotel."
Jacqueline 1-night trip
Posted less than an 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
  • 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 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?

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail: Visitors like this Middleton vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease 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. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Capital Brewery and Pheasant Branch Conservancy.

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.