Holiday houses in Lake Wingra

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Top-rated holiday rentals in Lake Wingra

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Guest favourite

Home in Madison

4.95 out of 5 average rating, 157 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 ;)

5–12 Nov

$248 NZD per night

Guest favourite

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.

22–29 Aug

$218 NZD per night

Guest favourite

Home in Madison

4.91 out of 5 average rating, 133 reviews

Tranquil Bay Creek Home: Ideal location

Tranquil Bay Creek Home: The Ideal location for all of your Madison Adventures ZTRHP1-2020-00049 Enjoy the very best of Madison from my comfortable, ideally situated home. You will enjoy off-street parking, locked storage for your bicycles and even sometimes eggs courtesy of my hens. (Update- retired my girls and hoping for new chicks soon.) *I adhere to all recommended cleaning/sanitizing protocols during the Covid-19 pandemic. I keep the house unrented for 3 to 5 days between guest stays.

19–26 Sep

$330 NZD per night

Guest favourite

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

15–22 Jan

$328 NZD per night

Guest favourite

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.

12–19 Oct

$177 NZD per night

Guest favourite

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.

8–15 Sep

$261 NZD per night

Guest favourite

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.

6–13 Aug

$208 NZD per night

Guest favourite

Guest suite in Madison

4.95 out of 5 average rating, 208 reviews

Downtown Condo, 5 blocks from Capital, Btn 2 Lakes

Entire first floor of a two story condo. Each floor has it's own private locked entrance. What you see in the pictures is all your space, NO SHARED SPACE. Great Downtown location. Grocery/Liquor store next door. 1 block from Sylvee (holds events/concerts), restaurants, Breeze Field (Holds events/concerts). 5 Blocks from the Capital/State Street/Overture Center/Orpheum Theatre/Majestic Theatre/Kohl Center/Monona Terrace Roof Top/Live on King St/Monona Terrace Convention Center.

12–19 Oct

$280 NZD per night

Guest favourite

Guest suite in Madison

4.96 out of 5 average rating, 358 reviews

Lake City Loft - Private Floor w/Spiral Staircase

Lake City Loft, with a spiral staircase entrance, encompasses the full 2nd story bungalow of a charming, remodeled 1915 home. Located on the outskirts of the eclectic Atwood neighborhood, guests will enjoy easy walking, biking, or driving access to nearby local favorite coffee shops, restaurants, breweries, & Lake Monona. The kitchenette boasts complimentary local coffee & beer that can be enjoyed on your own private balcony! We ONLY use non-toxic cleaning and toiletry products.

12–19 May

$269 NZD per night

Guest favourite

Guest suite in Madison

4.98 out of 5 average rating, 552 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.

12–17 May

$293 NZD per night

Guest favourite

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.

24–31 May

$285 NZD per night

Guest favourite

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.

20–27 Aug

$251 NZD per night