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Middleton Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Middleton vacation rentals

Smart TV, computer monitors

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, (9 reviews)
"This stay was truly perfect! Our hosts thought of every single detail and more. The property was perfectly appointed with all the little touches that made it ideal for a quiet couple's getaway just outside Madison. We drove nearly 8 hours north from Kansas City to get here, so imagine how wonderful it was to walk into a warm, cozy, welcoming house that had snacks on hand and a pizza delivery number front and center waiting for us! Best part of all - it was dog-friendly! Our dog immediately felt...
United States
Heather P.
$213 nightly
The price is $235
Aug 9 - Aug 10
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Terrace/patio

King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very Good, (5 reviews)
"Great place for a stay."
United States
Andy D.
$164 nightly
The price is $186
Aug 2 - Aug 3
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
1 bedroom, iron/ironing board, free WiFi, bed sheets

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, (28 reviews)
"A very unique place in a fantastic location! Little touches made our stay wonderful."
United States
Mike L.
$193 nightly
The price is $219
Jul 22 - Jul 23
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
2 bedrooms, WiFi, bed sheets

Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (22 reviews)
"Lovely place! It was clean and cozy. Perfect place while in town visiting family. "
United States
Jennifer G.
$248 nightly
The price is $274
Jul 15 - Jul 16
Total with taxes and fees
Charming Downtown Two Bedroom w/ Fireplace
Exterior

2 Bed/ 2 Bath At Cannery Square

2 Bed/ 2 Bath At Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (50 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
$303 nightly
The price is $341
Jul 15 - Jul 16
Total with taxes and fees
2 Bed/ 2 Bath At Cannery Square
Outdoor dining

A Room with a View

A Room with a View
Verona
9.2 out of 10, Wonderful, (48 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
$125 nightly
The price is $131
Jul 20 - Jul 21
Total with taxes and fees
A Room with a View
Exterior

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
$226 nightly
The price is $240
Jul 30 - Jul 31
Total with taxes and fees
Studio Apartment at Cannery Square
TV, fireplace, foosball, offices

Hot Tub - King Suite - Game Room - Large Groups

Hot Tub - King Suite - Game Room - Large Groups
Sun Prairie
10.0 out of 10, Exceptional, (21 reviews)
"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"
United States
George P.
$726 nightly
The price is $857
Jul 28 - Jul 29
Total with taxes and fees
Hot Tub - King Suite - Game Room - Large Groups
Reception

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (159 reviews)
"Amazing"
United States
Jennifer
$183 nightly
The price is $211
Jul 23 - Jul 24
Total with taxes and fees
The Dylin
Lobby

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$160 nightly
The price is $182
Jul 26 - Jul 27
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
Outdoor dining

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, (1 review)
"We had a great stay! Everything was as advertised and the sunset on the patio was the highlight."
United States
Michelle M.
$265 nightly
The price is $293
Jul 19 - Jul 20
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two
Property grounds

Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.2 out of 10, Very Good, (18 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
$463 nightly
The price is $521
Jul 16 - Jul 17
Total with taxes and fees
Waters Edge Cottage
Exterior

2 Bed/ 2 Bath At Cannery Square

2 Bed/ 2 Bath At Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (28 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
$317 nightly
The price is $357
Aug 11 - Aug 12
Total with taxes and fees
2 Bed/ 2 Bath At Cannery Square
Pool

Private Pool - Hot Tub - Game Room - 20 min DT

Private Pool - Hot Tub - Game Room - 20 min DT
Sun Prairie
10.0 out of 10, Exceptional, (6 reviews)
"We had a great family weekend in a great home that had plenty of space for all 12 of us. It was clean and the host was very accommodating and responsive. We will definitely look to stay there again on our next ski adventure. "
United States
Kylie V.
$939 nightly
The price is $1,039
Jul 15 - Jul 16
Total with taxes and fees
Private Pool - Hot Tub - Game Room - 20 min DT
Terrace/patio

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cozy Cabin on Crooked Lane close to Lake Wisconsin
Poynette
8.0 out of 10, Very Good, (2 reviews)
"Pet friendly cabin in the woods. Mostly updated and nice for 4-6 people. We stayed with our dogs and it worked well for us. "
United States
Jon A.
$367 nightly
The price is $387
Jul 27 - Jul 28
Total with taxes and fees
Cozy Cabin on Crooked Lane close to Lake Wisconsin
Dining

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (29 reviews)
"We had a great time and hope to return soon!"
United States
Jenna R.
$565 nightly
The price is $610
Aug 11 - Aug 12
Total with taxes and fees
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Lobby

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
$183 nightly
The price is $207
Jul 26 - Jul 27
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
3 bedrooms, free WiFi, bed sheets

Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
9.8 out of 10, Exceptional, (19 reviews)
"This was the perfect size home for a holiday family get together. Nice common spaces with enough areas to go when a little alone time was needed "
United States
Steve S.
$532 nightly
The price is $599
Jul 15 - Jul 16
Total with taxes and fees
Entire 3 Bedroom with Fireplace - sleeps 12
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
9.8 out of 10, Exceptional, (46 reviews)
"Great, comfortable stay. And close to shopping, which is just what I like to do! "
United States
Joyana A.
$560 nightly
The price is $630
Jul 19 - Jul 20
Total with taxes and fees
Capital City- 6 Miles from Madison with fireplace
Exterior

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.2 out of 10, Very Good, (14 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
$247 nightly
The price is $278
Aug 10 - Aug 11
Total with taxes and fees
Studio Apartment at Cannery Square
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

8/10 Good
"We had a nice stay"
Russell 1-night trip
Posted less than an hour 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 $131 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?

Waterfront Lodi Vacation Rental on Lake Wisconsin!: Visitors like this Middleton vacation home rental. It is located on the waterfront and has a patio, a selection of games, and air-conditioning 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.

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.