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Middleton Vacation Rentals

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Our top choices for Middleton vacation rentals

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, (7 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
Jul 6 - Jul 7
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

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 $187
Jul 5 - Jul 6
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub

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.
$341 nightly
The price is $377
Jul 27 - Jul 28
Total with taxes and fees
Charming Downtown Two Bedroom w/ Fireplace

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.
$193 nightly
The price is $219
Jul 1 - Jul 2
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

Hot Tub - King Suite - Game Room - Large Groups

Hot Tub - King Suite - Game Room - Large Groups
Sun Prairie
10.0 out of 10, Exceptional, (20 reviews)
"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"
United States
George P.
$702 nightly
The price is $828
Jul 1 - Jul 2
Total with taxes and fees
Hot Tub - King Suite - Game Room - Large Groups

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
$224 nightly
The price is $238
Jul 30 - Jul 31
Total with taxes and fees
Studio Apartment at Cannery Square

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (45 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
$124 nightly
The price is $131
Jul 13 - Jul 14
Total with taxes and fees
Enjoy Nature with Full Comfort!

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$162 nightly
The price is $184
Jul 1 - Jul 2
Total with taxes and fees
Pool with Slide. Great for Business Travelers!

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 2 - Jul 3
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two

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.
$320 nightly
The price is $360
Jul 15 - Jul 16
Total with taxes and fees
2 Bed/ 2 Bath At Cannery Square

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 $209
Jul 1 - Jul 2
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (28 reviews)
"We had a great time and hope to return soon!"
United States
Jenna R.
$536 nightly
The price is $578
Jul 14 - Jul 15
Total with taxes and fees
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

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 $388
Jul 6 - Jul 7
Total with taxes and fees
Cozy Cabin on Crooked Lane close to Lake Wisconsin

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (155 reviews)
"nice location"
United States
Mary
$153 nightly
The price is $177
Jul 5 - Jul 6
Total with taxes and fees
The Dylin

Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.0 out of 10, Very Good, (15 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
$455 nightly
The price is $512
Jul 5 - Jul 6
Total with taxes and fees
Waters Edge Cottage

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.
$496 nightly
The price is $563
Jul 2 - Jul 3
Total with taxes and fees
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Free Breakfast Pool & Hot Tub. Near East Towne Mall!

Free Breakfast Pool & Hot Tub. Near East Towne Mall!
Madison
10.0 out of 10, Exceptional, (1 review)
"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."
United States
Joy E.
$269 nightly
The price is $312
Jul 5 - Jul 6
Total with taxes and fees
Free Breakfast Pool & Hot Tub. Near East Towne Mall!

Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
9.8 out of 10, Exceptional, (45 reviews)
"Great, comfortable stay. And close to shopping, which is just what I like to do! "
United States
Joyana A.
$559 nightly
The price is $629
Jul 1 - Jul 2
Total with taxes and fees
Capital City- 6 Miles from Madison with fireplace

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)
"Great little lake house, close to downtown Madison. "
United States
LiHsin C.
$479 nightly
The price is $544
Jul 1 - Jul 2
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

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, (5 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.
$1,036 nightly
The price is $1,150
Jul 5 - Jul 6
Total with taxes and fees
Private Pool - Hot Tub - Game Room - 20 min DT
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

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?

Amazing townhouse, amazing attractions, amazing city!: Visitors like this Middleton vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.