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, 210 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 spacious sleeping area is showcased with a king bed dressed in soft linens and an earthy-toned coverlet. Decorative bedside lamps are positioned on each side, complementing the overall decor. Warm lighting from recessed fixtures gently illuminates the area.
Guest suite in Madison
4.92 out of 5 average rating, 181 reviews

Hospitality+Kitchen+Laundry+Gardens

Tastefully updated private suite on lower level of ranch. - KING bed plus twin bed, large bathroom, full kitchen, laundry W/D, work desk, dining table w/stools, comfortable furniture. Pristine clean. Close to grocery, many restaurants, parks, UW... Great for business needs (week and month long discounts!), moving to Madison, athletic events, visiting family... Tree lined street. Free parking. Owner lives on the property, but suite is private and not shared, as per Permit #ZTRHP1-2020-00004.

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, 183 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 living room is presented with large windows allowing natural light. A comfortable couch with decorative pillows faces a wooden coffee table, surrounded by two accent chairs. A woven stool adds texture, while standing lamps provide additional illumination. Minimalist art decorates the wall.
Bungalow in Madison
4.96 out of 5 average rating, 68 reviews

Sunny, spacious home, conveniently located.

Completely renovated, sunny and spacious bungalow in a conveniently-located, residential neighborhood. Newly refurnished for your enjoyment. Large living room, dining room, and full kitchen. Two bedrooms- one queen size bed, one full size bed and a queen sleeper-sofa. There is Wi-Fi, cable and Roku TV. Child- and family-friendly, with equipment and toys for the little ones. Quick and easy access to major roads and highways. 5-10 minutes from campus and downtown, 15 minutes from Epic.

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, 223 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.

Guest favourite
The exterior of the property is framed by lush greenery and blooming flowers. Soft lighting highlights the architectural features of the building, showcasing large windows that reflect the evening sky. A welcoming entrance leads toward a porch area nestled among the trees.
Home in Madison
4.87 out of 5 average rating, 93 reviews

Madison's Premier EcoLodge

Welcome to Premier Ecolodge on Monroe Street! Award winning 3800 sq. ft. home, with 3 guest rooms with queen beds and whirlpool baths, and 2 large bedrooms with for 4 beds, for a total of 12 guests. Relax in the sauna and enjoy a full kitchen to share your favorite meals. The house is near great restaurants, biking, running trails, and the Arboretum. Lake Wingra trail is across the street. UW and State Street are a mile away. Previous superhosts under new management.

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, 601 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.)

Top guest favourite
A cozy studio space is showcased, featuring a queen-sized bed adorned with red and white bedding. The kitchenette is visible in the background, along with a small dining area and desk beneath bright windows. Warm lighting enhances the overall inviting atmosphere.
Flat in Madison
4.98 out of 5 average rating, 41 reviews

Cozy Garden Apartment Near it All!

Stay in comfort at this peaceful and centrally-located place. Unwind in our cozy garden oasis after a day of exploring or visiting! This stylish well-lit studio basement apartment offers the perfect blend of comfort and convenience. Centrally located in a prime Madison Monroe Street neighborhood spot near shopping, dining, and UW or Edgewood sports venues, you'll have everything you need right at your fingertips.

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, 391 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
The bedroom is furnished with two spacious beds covered in patterned bedding. Two windows dressed in dark curtains allow filtered light to enter the room. A bedside table with a lamp stands between the beds, enhancing the inviting atmosphere.
Flat in Madison
4.77 out of 5 average rating, 453 reviews

Comfy space ideal for staycation or work from home

You’re going to truly 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