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

Middleton Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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.
$157 nightly
The price is $179
Oct 4 - Oct 5
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
A spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

2. 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, (16 reviews)
"Beautiful place, great stay."
United States
Thomas D.
$249 nightly
The price is $275
Oct 25 - Oct 26
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

3. 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
$127 nightly
The price is $147
Oct 28 - Oct 29
Total with taxes and fees
The Dylin
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

4. 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.
$119 nightly
The price is $126
Oct 12 - Oct 13
Total with taxes and fees
A Room with a View
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

5. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$170 nightly
The price is $193
Oct 4 - Oct 5
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
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
$190 nightly
The price is $215
Oct 11 - Oct 12
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A spacious living room with a fireplace, comfortable seating, and a television mounted above it.

7. Premium 3BR | Quick to Downtown

Premium 3BR | Quick to Downtown
Fitchburg
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful place with lots of room. "
United States
Brenda B.
$702 nightly
The price is $796
Oct 5 - Oct 6
Total with taxes and fees
Premium 3BR | Quick to Downtown
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.
$215 nightly
The price is $244
Oct 1 - Oct 2
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
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.

9. 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.
$297 nightly
The price is $334
Oct 6 - Oct 7
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
A modern living room with a sofa, coffee table, and dining area.

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

Historic Luxury 2-bedroom apartment in Cross Plains, WI
Cross Plains
$346 nightly
The price is $393
Sep 30 - Oct 1
Total with taxes and fees
Historic Luxury 2-bedroom apartment in Cross Plains, WI
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

11. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
$241 nightly
The price is $256
Oct 4 - Oct 5
Total with taxes and fees
Studio Apartment at Cannery Square
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

12. 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.
$218 nightly
The price is $241
Oct 11 - Oct 12
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

13. 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.
$413 nightly
The price is $468
Oct 12 - Oct 13
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

14. 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.
$458 nightly
The price is $529
Oct 8 - Oct 9
Total with taxes and fees
Doty ★ Walk to Everything -Hotel Quality- Downtown
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.
$297 nightly
The price is $334
Oct 19 - Oct 20
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
An outdoor seating area with wicker furniture and a central fire feature.

16. 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.
$220 nightly
The price is $254
Oct 4 - Oct 5
Total with taxes and fees
Accessible 1BR Suite w/ Tub | Hot 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, (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.
$339 nightly
The price is $381
Oct 4 - Oct 5
Total with taxes and fees
2 Bedroom Apartment Downtown Sun Prairie!
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.

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

Accessible 1BR Suite | Free Daily Breakfast & Pool
Madison
$219 nightly
The price is $253
Oct 4 - Oct 5
Total with taxes and fees
Accessible 1BR Suite | Free Daily Breakfast & Pool
A chalkboard sign with a welcome message and room instructions.

19. 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.
$501 nightly
The price is $564
Sep 30 - Oct 1
Total with taxes and fees
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

20. 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.
$390 nightly
The price is $443
Oct 27 - Oct 28
Total with taxes and fees
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
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

AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

10/10 Excellent
"Clean and pleasant stay breakfast was great hot and fresh"
Don 3-night trip
Posted 4 hours ago
AmericInn by Wyndham Madison West

Find out more about Middleton

Everything you need to know about Middleton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middleton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middleton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middleton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middleton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middleton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $126 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middleton rentals

At Expedia, we put the best Middleton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middleton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middleton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middleton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.