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Middleton Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 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
8.0 out of 10, Very good, (6 reviews)
"Great place for a stay."
United States
Andy D.
$155 nightly
The price is $176
Nov 1 - Nov 2
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, (17 reviews)
"Beautiful place, great stay."
United States
Thomas D.
$260 nightly
The price is $287
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, (195 reviews)
"Good location"
United States
ANCA
$122 nightly
The price is $141
Nov 1 - Nov 2
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, (56 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
$119 nightly
The price is $126
Oct 21 - Oct 22
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
$182 nightly
The price is $207
Oct 18 - Oct 19
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

6. 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, (33 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.
$220 nightly
The price is $250
Oct 18 - Oct 19
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
A hotel room with a sofa, a small table, a kitchenette, and a TV.

7. 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
$207 nightly
The price is $235
Oct 25 - Oct 26
Total with taxes and fees
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.

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

Historic Luxury 2-bedroom apartment in Cross Plains, WI
Cross Plains
$370 nightly
The price is $420
Oct 15 - Oct 16
Total with taxes and fees
Historic Luxury 2-bedroom apartment in Cross Plains, WI
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

9. 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.
$225 nightly
The price is $249
Oct 17 - Oct 18
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

10. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
$251 nightly
The price is $267
Oct 18 - Oct 19
Total with taxes and fees
Studio Apartment at Cannery Square
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.

11. 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.
$314 nightly
The price is $353
Oct 28 - Oct 29
Total with taxes and fees
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.

12. 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)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
$316 nightly
The price is $356
Oct 19 - Oct 20
Total with taxes and fees
2 Bed, 2 Bath Apartment at Cannery Square
Bright, open lobby seating area — a comfortable space to relax or catch up on work

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.
$236 nightly
The price is $272
Nov 1 - Nov 2
Total with taxes and fees
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A gym with treadmills, elliptical machines, and free weights.

14. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very good, (16 reviews)
"Great little town to stay the night. Woke early 5:30 am to tow truck towing cars in front lot. We luckily parked in back lot as instructed. Other than the noise of this unfortunate event, we enjoyed our stay. Loved the town and many places to walk to. Pizza place was amazing!"
United States
Cheryl B.
$244 nightly
The price is $275
Oct 28 - Oct 29
Total with taxes and fees
Studio Apartment at Cannery Square
A modern kitchen with a refrigerator, microwave, and bar stools.

15. 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.
$362 nightly
The price is $407
Oct 15 - Oct 16
Total with taxes and fees
2 Bedroom Apartment Downtown Sun Prairie!
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

16. 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.
$250 nightly
The price is $276
Nov 1 - Nov 2
Total with taxes and fees
Charming Downtown Two Bedroom w/ Fireplace
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

17. 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)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
$399 nightly
The price is $452
Nov 1 - Nov 2
Total with taxes and fees
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A kitchen with a sliding glass door leading to a wooden deck with a view of a grassy field and a lake.

18. Updated home with lake views, across the street from Lake WI, near free ferry

Updated home with lake views, across the street from Lake WI, near free ferry
Merrimac
10.0 out of 10, Exceptional, (47 reviews)
"Very clean property, exactly as advertised. Host was easy to work with."
United States
Jacob M.
$301 nightly
The price is $339
Oct 15 - Oct 16
Total with taxes and fees
Updated home with lake views, across the street from Lake WI, near free ferry
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, (24 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
$531 nightly
The price is $597
Nov 1 - Nov 2
Total with taxes and fees
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
A spacious dining area with a high ceiling and large windows, wooden furniture, and a view of the outdoors.

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

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.6 out of 10, Exceptional, (30 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.
$350 nightly
The price is $378
Oct 19 - Oct 20
Total with taxes and fees
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
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

Tru by Hilton Madison West, WI

Tru by Hilton Madison West, WI

10/10 Excellent
"Great staff"
Rod 1-night trip
Posted less than an hour ago
Tru by Hilton Madison West, WI

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.