Middleton Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

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, (6 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.
$208 nightly
The price is $230
Jun 1 - Jun 2
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.
$142 nightly
The price is $162
May 31 - Jun 1
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
Outdoor dining

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (43 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
$128 nightly
The price is $135
Jun 9 - Jun 10
Total with taxes and fees
Enjoy Nature with Full Comfort!
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, (26 reviews)
"A very unique place in a fantastic location! Little touches made our stay wonderful."
United States
Mike L.
$208 nightly
The price is $236
May 31 - Jun 1
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Exterior

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
$219 nightly
The price is $232
May 31 - Jun 1
Total with taxes and fees
Studio Apartment at Cannery Square
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.
2 Bed/ 2 Bath At Cannery Square
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.
$284 nightly
The price is $320
May 31 - Jun 1
Total with taxes and fees
2 Bed/ 2 Bath At Cannery Square
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.
$290 nightly
The price is $305
Jun 1 - Jun 2
Total with taxes and fees
Cozy Cabin on Crooked Lane close to Lake Wisconsin
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, (19 reviews)
"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"
United States
George P.
$568 nightly
The price is $675
Jun 2 - Jun 3
Total with taxes and fees
Hot Tub - King Suite - Game Room - Large Groups
Fridge, microwave, oven, stovetop

2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (40 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
Jun 9 - Jun 10
Total with taxes and fees
2 Bedroom Apartment Downtown Sun Prairie!
Fridge, microwave, oven, stovetop

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

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (13 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
$398 nightly
The price is $451
May 31 - Jun 1
Total with taxes and fees
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Dining

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (27 reviews)
"We were looking for a peaceful getaway and place to unwind distress and relax… Speaking with Brittany was quick and easy, we knew that this was the place for us. Booking was easy and the directions to get there were a breeze… The property is beautiful in the home was everything we hoped it would be and more."
United States
Ryan F.
$449 nightly
The price is $485
Jun 2 - Jun 3
Total with taxes and fees
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
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
$214 nightly
The price is $236
Jun 10 - Jun 11
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two
Lobby

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$161 nightly
The price is $182
May 31 - Jun 1
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
Exterior

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very Good, (13 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
$243 nightly
The price is $273
May 31 - Jun 1
Total with taxes and fees
Studio Apartment at Cannery Square
Reception

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (145 reviews)
"nice location"
United States
Mary
$126 nightly
The price is $146
Jun 30 - Jul 1
Total with taxes and fees
The Dylin
Property grounds

Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.0 out of 10, Very Good, (13 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
$455 nightly
The price is $512
Jun 1 - Jun 2
Total with taxes and fees
Waters Edge Cottage
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
$184 nightly
The price is $208
Jun 4 - Jun 5
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Outdoor spa tub

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, (4 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.
$906 nightly
The price is $1,005
Jun 3 - Jun 4
Total with taxes and fees
Private Pool - Hot Tub - Game Room - 20 min DT
Exterior

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, (52 reviews)
"The location is wonderful. The river setting is beautiful. The pelicans are so fun to watch. Enjoyed all the rooms with tvs."
United States
Robert
$439 nightly
The price is $498
May 31 - Jun 1
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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
"I absolutely love this place! Second time going there as I had appointments at the UW. Everything is very close and convenient you cannot go wrong! This hotel is the cleanest hotel I have ever stayed at. The beds are very comfortable, lots of tv channels, very nice pool and hot tub area, very nice staff, excellent breakfast lots to choose from, happy hour from 5-7 to mingle with people and hotel supplies popcorn, nachos and cheese, wine or beer. You will not be disappointed by staying here! Like I said, extremely clean and wonderful staff."
Jennifer 2-night trip
Posted 2 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 $135 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: You might want to consider this vacation home rental near Middleton, which 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 4 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 Pleasant View Golf Course.

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.