Vacation rentals in Middleton

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Top-rated vacation rentals in Middleton

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Guest favorite

Guesthouse in Mount Horeb

4.97 out of 5 average rating, 544 reviews

Cool, Scenic Country Art Studio

Creative souls love my marvelous studio retreat, a delightful space that features tall ceilings and an open design--giving it a loft feel with an expansive view of a picturesque barn, pasture, and wooded hills. This amazing, heated, spacious country getaway has no plumbing— it's just a few steps across the yard to the main house guest bathroom. Come create, relax, and renew here! Well-behaved dogs included in your online reservation, must be leashed when outside, and kenneled in your absence.

Aug 17 – 24

R2,275 ZAR per night

Guest favorite

Home in Madison

4.95 out of 5 average rating, 155 reviews

Grooviest | Quiet | Close | Upscale MCM | Records!

• ALL NEW RENOVATION, BRAND NEW LINENS, TOWELS, ETC • Two floor private home • Private backyard with patio & fire pits • Two TVs, one in living room, one in dining room • Luxury Mid Century Modern Stereo Console with records, bluetooth • Over 70 classic albums to listen to (jazz, rock, classical, eclectic) • Access to over 1000 classic albums at our downtown Music Studio • Electric fireplace with multi heat settings • Full Size Kitchen, Full Size Appliances, Fully stocked • Vintage Bar Cart ;)

Nov 5 – 12

R2,565 ZAR per night

Guest favorite

Guest suite in Madison

4.97 out of 5 average rating, 297 reviews

Private & Clean Apartment Near Downtown & Airport

Private, sunny basement unit with separate entry accessible by keycode. 1 bedroom (queen), full bath, sitting area (2 twins/king bed), desk, WI-FI, TV, mini fridge, microwave, & coffee/tea. On street parking. Kid friendly! Note: We live with kids above the apartment - you will hear us walking around & some water pipes. 2-4 mi from Airport, Capitol, & UW Campus. Walk to brunch, pub, jazz lounge, bubble tea, grocery store, park, & bike path. Licensed by City & State. Paying all taxes & fees.

Aug 14 – 21

R2,137 ZAR per night

Guest favorite

Guest suite in Madison

4.99 out of 5 average rating, 149 reviews

Peaceful 2 BR/1 BA w/ patio, firepit & pool table

• 1400 sq.ft. lower level suite • Private backyard with patio & gas fire pit • Two TVs • Electric fireplace • Pool and Air hockey table • Stocked kitchenette w/ bar seating area • Workspace • Blackout shades and curtains • Onsite parking in driveway for one vehicle • Ample street parking • 16-min drive to UW campus and downtown • 9-min drive to the airport • 6-min drive to shopping and restaurants • Extremely safe neighborhood • License No. LICHMD-2022-00079 • Zone Permit ZTRHP1-2022-00005

Apr 2 – 9

R3,033 ZAR per night

Guest favorite

Guest suite in Middleton

5.0 out of 5 average rating, 115 reviews

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with two skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with walk-in shower, this comfortable space has all the amenities perfect for a quick weekend getaway or a week-long business trip. The studio adjoins a house but has its own outdoor entrance and is soundproofed for privacy. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

Oct 8 – 15

R1,715 ZAR per night

Guest favorite

Home in Madison

4.99 out of 5 average rating, 301 reviews

Beautiful 3 Bedroom Apartment, Kitchen, Fireplace

Private lower level 1600sq ft apartment. Steps away from TPC Wisconsin! Follow the path to the back of the main house, here you'll find a beautiful space with large windows and plenty of natural light. Enjoy the warm gas fireplace, large flat screen TV. Make meals in the generous farmhouse kitchen. Sorry no full-size oven. Relax on the paved patio overlooking the wetlands and listen to many birds. Just a 5 min drive to the airport and close to downtown. TPC WISCONSIN OPENING 8/2023

Oct 9 – 16

R3,676 ZAR per night

Guest favorite

Guest suite in Sun Prairie

4.89 out of 5 average rating, 247 reviews

Entire Countryside Garden Suite, Peaceful Retreat

Welcome to our home! We have upgraded our Garden Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

Feb 4 – 11

R1,697 ZAR per night

Guest favorite

Guesthouse in Madison

4.92 out of 5 average rating, 245 reviews

Historic guesthouse near downtown, hospital and UW

Featured on the National Register of Historic Places, this unique 1916 “granny cottage" stands behind our home in the gorgeous Village of Shorewood Hills. Centrally located, we are just a few walkable blocks from UW Hospital and Picnic Point, and walking/biking distance from UW, the Capitol, Hilldale Shopping Mall, Whole Foods and plenty of restaurants. Because we are in a quiet neighborhood, we have a 3 guest maximum. This is a place to retreat and relax and enjoy the best of Madison.

Sep 12 – 19

R2,996 ZAR per night

Guest favorite

Apartment in Verona

4.97 out of 5 average rating, 216 reviews

Spacious Basement Apartment near Epic and Madison

We first used AirBnB when we traveled to Paris and Barcelona in 2015. We were happy with our stay but thought there was room for improvements. When we purchased our home in Verona we saw the potential for using part of it for AirBnB. From our experiences, we designed and decorated our space with a simple focus – what would we want in a nightly rental. The result was a spacious, clutter-free, and cheerful place where guests could feel comfortable while away from their own homes.

Oct 8 – 15

R3,063 ZAR per night

Guest favorite

Guest suite in Madison

4.98 out of 5 average rating, 551 reviews

DT+Bikes+Pvt Suite+Jacuzzi+Parking+Near Campus

We are located in a unique pocket of downtown Madison, directly across from Brittingham Park, Monona Bay, Brittingham Boat Rental & a bike/walking/running path. We are a short walk from UW-Madison, Hospitals, State Street & the Capitol. You will love our welcoming neighborhood! We have a friendly dog, Bella, who stay upstairs with us, but you could see her wandering outside. We have been inspected and are licensed with the City of Madison. ZTRHP1-2020-00027.

May 12 – 17

R2,818 ZAR per night

Guest favorite

Apartment in Madison

4.96 out of 5 average rating, 104 reviews

Private entry flat near Atwood neighborhood

No cleaning fee!! Enjoy your visit to Madison in this sunny one bedroom apartment with private entrance and off street parking. It's great location is within walking distance to the Schenk/Atwood neighborhood, with numerous restaurants, cafes and music venues. Within 2 miles of the state capitol, Monona Terrace, and 3 miles from the airport, Kohl Center and Camp Randall. Perfectly suited for couples, solo adventurers, or business travelers.

May 24 – 31

R2,970 ZAR per night

Guest favorite

Loft in McFarland

4.97 out of 5 average rating, 113 reviews

Private Loft in Historic McFarland House

This newly remodeled unit is located in the attic of the Historic McFarland House, built in 1857 in the community that bears its name. Nestled in our small suburban downtown, this unit is perfect for travelers visiting the Madison area or nomads making a pit stop in the mid-west. Only 8mi to campus or a quick commute to the capitol, McFarland is an easy exit off multiple highways and interstates.

Aug 18 – 25

R2,370 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Middleton vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Middleton's top sights

Hubbard Avenue Diner14 locals recommend

Greenway Station3 locals recommend

National Mustard Museum12 locals recommend

Original Pancake House12 locals recommend

Willy Street Co-op—West25 locals recommend

Craftsman Table & Tap7 locals recommend

Other great vacation rentals in Middleton

Guest favorite

Guesthouse in Sun Prairie

4.98 out of 5 average rating, 307 reviews

Charming Milkhouse Cottage, minutes from Madison!

Feb 19 – 26

R2,991 ZAR per night

Guest favorite

Guest suite in Mount Horeb

4.89 out of 5 average rating, 141 reviews

Nestled Valley

Oct 28 – Nov 4

R2,089 ZAR per night

Guest favorite

Tiny home in Darlington

4.98 out of 5 average rating, 246 reviews

The Bower- Peaceful farm stay getaway.

Dec 31 – Jan 7

R1,877 ZAR per night

Guest favorite

Guest suite in Madison

4.95 out of 5 average rating, 208 reviews

Downtown Condo, 5 blocks from Capital, Btn 2 Lakes

Oct 7 – 14

R2,650 ZAR per night

Guest favorite

Home in Madison

4.95 out of 5 average rating, 304 reviews

Cottage Suite + Whirlpool Tub.

Feb 26 – Mar 5

R3,202 ZAR per night

Guest favorite

Home in Madison

4.88 out of 5 average rating, 210 reviews

Private apartment -2 Beds, Kitchen Office, Sunroom

Aug 18 – 25

R2,791 ZAR per night

Guest favorite

Guest suite in Madison

4.97 out of 5 average rating, 479 reviews

Lakefront downtown private 3 BR. Kayaks. Hot tub.

Oct 10 – 17

R10,524 ZAR per night

Guest favorite

Cottage in Arena

4.91 out of 5 average rating, 263 reviews

Sugarland Cottage

Aug 29 – Sep 5

R2,530 ZAR per night

Show all

Quick stats about vacation rentals in Middleton

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
880 reviews
Nightly prices starting at
R573 ZAR before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Middleton?
Yes! Work meets play with ease at over 10 vacation rentals in Middleton featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Middleton?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Middleton have wifi?
Absolutely! We offer over 10 house rentals with wifi in Middleton. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Middleton have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Middleton. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Middleton?
Middleton has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Middleton?
Experience the best of Middleton with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Vacation rentals in Middleton

Top-rated vacation rentals in Middleton

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Middleton vacation rentals

Stay near Middleton's top sights

Other great vacation rentals in Middleton

Guesthouse in Sun Prairie

Guest suite in Mount Horeb

Tiny home in Darlington

Guest suite in Madison

Home in Madison

Home in Madison

Guest suite in Madison

Cottage in Arena

Quick stats about vacation rentals in Middleton

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Middleton?

What are the most popular amenities for House Rentals in Middleton?

Do house rentals in Middleton have wifi?

Do house rentals in Middleton have air conditioning?

Are there family-friendly vacation rentals in Middleton?

How much does it cost to stay in house rentals in Middleton?

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