Holiday rentals in Lake Wingra

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Top-rated holiday rentals in Lake Wingra

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Top guest favourite
A branch adorned with delicate white flowers is positioned in a vase on a table, creating a soft focal point. In the background, a spacious bed is partially visible, with natural light entering from a window, enhancing the bright interior.
Loft in McFarland
4.97 out of 5 average rating, 211 reviews

#301 Private Apartment in Historic McFarland House

*** Our 2nd Floor is being remodeled throughout 2025 adding 4 more units to the old 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.

Top guest favourite
A bedroom features a spacious bed adorned with a light blue coverlet. Framed artwork decorates the walls, and a bedside lamp provides soft lighting. A small desk and chair are positioned beside the bed, enhancing the room's functionality.
Guest suite in Madison
4.98 out of 5 average rating, 628 reviews

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

Located in a unique pocket of DT, across from Brittingham Park, Monona Bay, Brittingham Boat Rental & a bike/walking path. You will love our welcoming neighborhood! We are a short walk from UW-Madison, Hospitals, State Street & the Capitol. We have a dog, Bella, who stay upstairs, but you could see her wandering outside. We have been inspected & are licensed with the city. ZTRHP1-2020-00027. Ask prior to arrival about the use of our high-quality mid-drive ebikes when you stay (for a small fee).

Top guest favourite
A two-story home with a mix of stone and wood siding sits on a grassy lot. Large windows allow natural light inside. A paved driveway leads to the garage, with trees and a view of open land in the background.
Guest suite in Sun Prairie
4.89 out of 5 average rating, 386 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) 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.

Top guest favourite
A cozy outdoor space is featured with a wooden pergola providing shade, surrounded by blue siding. Seating includes two cushioned chairs and a swing chair, all arranged around a fire table set on a patterned rug, enhancing the inviting atmosphere.
Guest suite in Madison
4.95 out of 5 average rating, 399 reviews

Cottage Suite + Jacuzzi Tub & Sauna

This Suite is perfect for 1-4 people seeking convenient proximity to most things Madison 10-15 minutes to downtown. *Freshly remodeled guest dedicated- full 1st floor private suite. You will enjoy a bright- enclosed front porch & welcoming pergola in back. *Please note: 2nd floor is a seperate apartment. Fast WIFI●Infrared Sauna●2 Smart TV 's●Full Kitchen●Washer/Dryer●Dishwasher ●Off-Street parking●Quiet neighborhood ●Reverse osmosis H²O●Smart lock's●Jacuzzi tub/shower●Shampoo/Cond./Bodywash

Guest favourite
An A-frame interior showcases a spiral staircase leading to the loft, surrounded by natural wood and brick accents. A large television is mounted above a fireplace, complemented by decorative plants and a wall clock. Colorful patterns can be seen in the ceiling lights.
Home in Madison
4.95 out of 5 average rating, 184 reviews

ONE OF A KIND vacation rental with a view

Arbor Hill House - Unique A-frame vacation rental perched atop a hill with great views overlooking the Beltline, UW Arboretum and the city of Madison. Excellent central location with easy access to all of Madison and surrounding areas. I'll be happy to do whatever I can to make your stay a pleasant one. Please keep things clean and be respectful. The home should not be used for parties or events. If you have any questions please feel free to ask. I look forward to sharing my home with you.

Top guest favourite
A spacious loft is characterized by vaulted ceilings and exposed wooden beams. Natural light floods in through multiple skylights, highlighting a comfortable seating area with a gray sofa, a neutral accent chair, and a vibrant yellow pouf. A small desk and chair are positioned against one wall, while a smart TV sits across from the seating area.
Home in Madison
4.97 out of 5 average rating, 219 reviews

Lakeview Loft - Downtown Madison

Stay in the heart of Madison, enjoying exclusive access to our 3rd floor suite with lake views. Located on a quiet street along the Lake Loop bike path/Lake Monona, and close to Willy Street (0.3 mi), the Sylvee (1.1 mi), the Capitol (1.7 mi), Monona Terrace (1.6 mi), and Camp Randall (3.3 mi). Self check-in with keypad and ample parking. Wifi is over 500 Mbps download/upload speeds. #ZTRHP1-2022-00022 Note: Loft is accessed by 3 flights of stairs! Space has coffee bar only (no kitchen).

Top guest favourite
A spacious studio featuring two green upholstered benches arranged on a decorative area rug. Natural light floods the room through skylights, illuminating the cozy sleeping area with a large bed and a dining nook equipped with a small table and chairs.
Guest suite in Middleton
4.99 out of 5 average rating, 224 reviews

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with a 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 and is up a flight of stairs through a separate outdoor entrance. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

Superhost
An open living space is depicted with a large dining table at the center, surrounded by two wooden stools. A light-colored sofa is positioned to the right, with several cushions. Potted plants add a touch of greenery, while a wall-mounted coat rack displays outerwear.
Guest suite in Madison
4.92 out of 5 average rating, 310 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.

Top guest favourite
The outdoor area of the home is visible, featuring a spiral staircase leading to a deck with a covered area. A hot tub is positioned on the patio below, surrounded by lush greenery and string lights hanging above, providing a relaxed and inviting ambiance.
Guest suite in Madison
4.96 out of 5 average rating, 602 reviews

Lakefront 3BR Retreat – Sauna · HotTub · Fireplace

Stay in your private 3BR, 2BA section of our lakefront downtown home. Enjoy lake access, a hot tub, sauna, fireplace, and calm views plus you're steps from restaurants in the Willy St. neighborhood and on the bike path. Relax with coffee on the dock, play board games, or roast marshmallows by the fire. Cozy up indoors with parking, a full kitchen for holiday meals, and festive seasonal touches. (Paddleboards and pontoon available in warmer months.)

Guest favourite
A modern kitchen features exposed wooden beams and a spacious island with a large marble countertop. Red chairs are arranged around the island, complemented by stainless steel appliances and white cabinetry. Natural light filters in through the windows, enhancing the design.
Home in Madison
4.93 out of 5 average rating, 164 reviews

Doty ★ Walk to Everything -Hotel Quality- Downtown

Welcome to our modern second story space in downtown Madison. 3 bedrooms with a beautiful kitchen and beer in the fridge. No need to Uber, you're just a few blocks from all the venues around the Capitol square, State St, and Kohl Center. Easy to get to the UW-Campus, Sylvee, Alliant Energy Center, and all the bars/restaurants in Madison. Business friendly, and free access to co-working space a couple blocks away.

Top guest favourite
A spacious dining area features a rectangular table set with a checkered tablecloth and surrounded by blue chairs. A decorative arrangement of flowers sits at the center of the table, and a patterned rug adds warmth to the space. Shelving with books is visible in the background.
Guest suite in Madison
4.94 out of 5 average rating, 392 reviews

Far Westside Home Away From Home

Your own 820 square foot space with full bathroom. Located 6.2 miles from the UW Madison. Inside, you will find a bedroom with a queen bed, a queen size comfortable hide-a-bed sofa, a 42" HDTV, a kitchenette w/a dining room table, a mini-fridge, an elliptical, and a library. To see a video of the space go to YouTube and search on “v=hDgEasBTxoA” (cut and paste recommended). ZTRHP1-2020-00044

Guest favourite
A spacious bedroom is featured with two queen beds, each adorned with subtle striped bedding. Soft lighting from a bedside lamp illuminates the room, while floor-to-ceiling curtains partially cover large windows, allowing natural light to filter in.
Flat in Madison
4.8 out of 5 average rating, 466 reviews

Immaculate apartment steps from Camp Randall!

Enjoy this spacious apartment ideal for a staycation or work-from-home alternative. Located in the shadow of Camp Randall this apartment is walking distance to great restaurants, grocery and retail. Great walking and biking paths are just blocks away connecting you to the whole city of Madison. The Space is not suitable for large groups events or parties.

Popular amenities for Lake Wingra holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Dane County
  5. Madison
  6. Lake Wingra