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Holiday Rentals in Middleton

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Our top choices for Middleton holiday 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.
The price is €217
includes taxes & fees
6 Jul - 7 Jul
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.
The price is €166
includes taxes & fees
5 Jul - 6 Jul
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.
The price is €334
includes taxes & fees
27 Jul - 28 Jul
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.
The price is €199
includes taxes & fees
6 Jul - 7 Jul
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.
The price is €833
includes taxes & fees
8 Jul - 9 Jul
Hot Tub - King Suite - Game Room - Large Groups

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
The price is €212
includes taxes & fees
2 Aug - 3 Aug
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.
The price is €118
includes taxes & fees
13 Jul - 14 Jul
Enjoy Nature with Full Comfort!

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is €164
includes taxes & fees
30 Jul - 31 Jul
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.
The price is €266
includes taxes & fees
19 Jul - 20 Jul
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.
The price is €326
includes taxes & fees
14 Jul - 15 Jul
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
The price is €187
includes taxes & fees
3 Jul - 4 Jul
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.
The price is €494
includes taxes & fees
14 Jul - 15 Jul
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.
The price is €339
includes taxes & fees
16 Jul - 17 Jul
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, (156 reviews)
"nice location"
United States
Mary
The price is €129
includes taxes & fees
9 Jul - 10 Jul
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.
The price is €448
includes taxes & fees
5 Jul - 6 Jul
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.
The price is €478
includes taxes & fees
20 Jul - 21 Jul
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)
The price is €283
includes taxes & fees
5 Jul - 6 Jul
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.
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.
The price is €518
includes taxes & fees
20 Jul - 21 Jul
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, (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.
The price is €998
includes taxes & fees
5 Jul - 6 Jul
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middleton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middleton holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middleton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middleton holiday rentals we have selected for you start as low as €118 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middleton rentals

At Expedia, we put the best Middleton holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Middleton?

Yes, there are holiday rentals close to the most popular sights in Middleton, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Middleton. Make sure you have time to check out the cafés and football games during your trip.

What are some of the best holiday rentals that Middleton has to offer?

Amazing townhouse, amazing attractions, amazing city!: This holiday home rental outside of Middleton offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Middleton?

Choose from 4 Expedia holiday rentals in Middleton for a memorable holiday.

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 holiday rental in Middleton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleton. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family gatherings.