A calm body of water reflecting a sunset sky with scattered clouds.

Middleton Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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
8.4 out of 10, Very good, (7 reviews)
"Great place for a stay."
United States
Andy D.
The price is ￥25,269
￥31,552 total
includes taxes & fees
Dec 15 - Dec 16
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, (217 reviews)
"Good location"
United States
ANCA
The price is ￥15,805
￥18,254 total
includes taxes & fees
Dec 6 - Dec 7
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, (59 reviews)
"Enjoyed the county setting and seeing the cranes and hearing the rooster crow!"
United States
Elizabeth C.
The price is ￥13,751
￥19,905 total
includes taxes & fees
Dec 7 - Dec 8
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 ￥26,048
￥33,373 total
includes taxes & fees
Nov 16 - Nov 17
Pool with Slide. Great for Business Travelers!
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

5. 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, (34 reviews)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
The price is ￥20,762
￥38,974 total
includes taxes & fees
Nov 21 - Nov 22
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
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 ￥37,249
￥47,276 total
includes taxes & fees
Dec 15 - Dec 16
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

7. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is ￥12,937
￥38,676 total
includes taxes & fees
Nov 19 - Nov 20
Studio Apartment at Cannery Square
A modern living room with a sofa, coffee table, and dining area.

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

Historic Luxury 2-bedroom apartment in Cross Plains, WI
Cross Plains
The price is ￥35,935
￥63,990 total
includes taxes & fees
Dec 14 - Dec 15
Historic Luxury 2-bedroom apartment in Cross Plains, WI
A modern living room with a flat-screen TV, leather seating, a ceiling fan, and large windows.

9. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (56 reviews)
"Great and easy stay! The place was comfortable and inviting. Would stay again!"
United States
Taylor S.
The price is ￥20,922
￥52,286 total
includes taxes & fees
Dec 2 - Dec 3
2 Bed, 2 Bath Apartment at Cannery Square
A modern room with a kitchenette, a bed, a sofa, and a TV.

10. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.6 out of 10, Excellent, (17 reviews)
"Great location - able to walk to many stores and restaurants. Spacious for a studio and very quiet."
United States
Martha T.
The price is ￥18,526
￥42,043 total
includes taxes & fees
Dec 5 - Dec 6
Studio Apartment at Cannery Square
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

11. Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (28 reviews)
"Amazing location, nicely furnished and cozy!"
United States
Heather & Nick V.
The price is ￥20,123
￥40,944 total
includes taxes & fees
Nov 30 - Dec 1
Charming Downtown Two Bedroom w/ Fireplace
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.

12. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (31 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is ￥20,283
￥51,567 total
includes taxes & fees
Nov 19 - Nov 20
2 Bed, 2 Bath Apartment at Cannery Square
An outdoor seating area with wicker furniture and a central fire feature.

13. 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 ￥31,690
￥40,215 total
includes taxes & fees
Nov 29 - Nov 30
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

14. 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 ￥27,310
￥42,179 total
includes taxes & fees
Nov 18 - Nov 19
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.

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

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (48 reviews)
"Great stay! Very close to everything downtown."
United States
Garrett M.
The price is ￥30,539
￥48,200 total
includes taxes & fees
Nov 16 - Nov 17
Doty ★ Walk to Everything -Hotel Quality- Downtown
An outdoor seating area with wicker furniture and a central fire feature.

16. Accessible 1BR Suite | Free Daily Breakfast & Pool

Accessible 1BR Suite | Free Daily Breakfast & Pool
Madison
The price is ￥31,655
￥39,064 total
includes taxes & fees
Nov 29 - Nov 30
Accessible 1BR Suite | Free Daily Breakfast & Pool
A modern kitchen with a refrigerator, microwave, and bar stools.

17. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (43 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 ￥30,824
￥62,169 total
includes taxes & fees
Nov 15 - Nov 16
2 Bedroom Apartment Downtown Sun Prairie!
A spacious dining area with a high ceiling and large windows, wooden furniture, and a view of the outdoors.

18. Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (32 reviews)
"Great Place Beautiful landscape from the deckHost was very responsive Would go back again in a heartbeat Everything you need for a great stay"
United States
John W.
The price is ￥33,063
￥65,834 total
includes taxes & fees
Nov 15 - Nov 16
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
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, (20 reviews)
"Everything was very nice"
United States
Anonymous traveler
The price is ￥23,670
￥67,334 total
includes taxes & fees
Nov 16 - Nov 17
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A modern kitchen with a central island, dining area with a round table, and a visible refrigerator.

20. Charming 3-bedroom house on Madison's Eastside! Close to everything!

Charming 3-bedroom house on Madison's Eastside! Close to everything!
Madison
The price is ￥57,560
￥92,336 total
includes taxes & fees
Nov 17 - Nov 18
Charming 3-bedroom house on Madison's Eastside! Close to everything!
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

Fairfield Inn & Suites by Marriott Madison West/Middleton

Fairfield Inn & Suites by Marriott Madison West/Middleton

10/10 Excellent
"Very courteous staff"
harvey 1-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott Madison West/Middleton

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 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.