Vacation rentals in Lake Wingra

The exterior of the historical Plough Inn features a two-story building with a white facade and green trim. Large green-framed windows offer a glimpse of the interior. Surrounding greenery and sparse snow patches highlight the natural setting, contributing to a serene neighborhood atmosphere.

4.93 out of 5 average rating, 60 reviews

Madison Historical Inn

The lower level of this historical building, the Plough Inn, 1853, was a tavern at the outskirts of Madison. It is now part of the city center, close to the University, State Capitol, Edgewood College, and restaurants. Wingra Lake and Park are just across. The guesthouse has been fully rehabilitated by the previous owners, respecting its historical cachet and hard-wood floors, but remodeled to today's standards. The rooms are spacious, each with their own character and bath. It is a cozy place.

4.96 out of 5 average rating, 137 reviews

Apartment in McFarland

#302 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 1856 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.

A comfortable living area features a black leather sofa adorned with red and yellow pillows. A wooden coffee table sits in front, and a colorful area rug adds warmth to the space. The background reveals a well-lit kitchen with modern fixtures.

4.97 out of 5 average rating, 238 reviews

4-Bedroom Lathrop Home by UW/Camp Randall -Madison

Home steps to Camp Randall & a short walk to UW Madison! $375 / night (up to 5 guests); Extra guests $75 / night after the 5th guest ($1045 Nightly Rate up to 10 people max) $495 / night during Badger game days (up to 5 guests; $65 / night / guest after the 5th guest) Our back patio is also available to guests; however, please know that we use the garage & part of the driveway for tailgating with friends & family during Badgers football games. Cleaning Fee $150. No Pets or Smoking allowed.

4.91 out of 5 average rating, 175 reviews

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

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.

4.95 out of 5 average rating, 19 reviews

A kitchenette is framed by an arched entryway, showcasing teal subway tiles and open shelving. Kitchen essentials, including glassware and utensils, are neatly arranged. A black refrigerator and microwave are positioned alongside a stainless steel countertop with a modern gas range.

Apartment in Madison

Historic Downtown Studio. Unit I. Construc. Close

Historic charm meets modern comfort in the heart of downtown. This bright, spacious studio features a kitchen, separate dining room, and plenty of storage. Enjoy access to a shared rooftop deck overlooking top restaurants. Hosted by Voyageur Stays—a locally owned, husband-and-wife-run company passionate about handcrafted, thoughtfully curated spaces. Second floor walk-up. Construction nearby. Note: week of August 4-August 15 construction work in the alley next to unit from 8-5 pm weekdays.

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.

4.97 out of 5 average rating, 197 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).

4.95 out of 5 average rating, 59 reviews

A spacious studio area features a comfortable queen-sized Murphy bed dressed in white linens. An accent chair in a soft blue is positioned beside a wooden dresser. Natural light spills from a window above, and a room divider offers additional privacy options.

Apartment in Madison

Camp Randall - FREE parking! Walk to everywhere!

Welcome! Steps from the UW, Camp Randall, Edgewood College, Vilas Zoo, the bike path system, EPIC, all 3 local hospitals, downtown, the Capitol, & the lakes. With a combined 80+ years living in Madison, we’re available to you & will do everything in our power to provide for anything you may need as our guest. We’ve raised our family in this home over the past 25 years & look forward to hosting you! We allow dogs, but I’m afraid no cats. PLEASE read the ENTIRE description before booking!

4.99 out of 5 average rating, 200 reviews

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

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.

4.98 out of 5 average rating, 772 reviews

A cottage nestled among tall trees is visible, with a charming front porch featured. Vibrant pink flowers bloom vividly in the foreground, adding color to the lush green grass surrounding the property.

Tiny home in Darlington

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

A green yard is framed by tall trees, including conifers and a large deciduous tree. A colorful, whimsical fence in shades of purple and green can be seen along a mulched path leading toward the house, which features a light-colored exterior and a serene atmosphere.

5 out of 5 average rating, 310 reviews

The Rainbow House *lower-level*

Quiet / peaceful / positive vibes place perfect for a couple but can do one more (twin-size floor mattress / PacknPlay). *NOTE: Must pre-approve pets with initial booking & only booked guests allowed - this is how we feel most safe hosting in our home. No smokers (of any kind) here. Strict quiet hours. My wife Marla and I are so happy to share our sweet sunny lower-level space with you - she built it herself! We live upstairs with our adorable rescue dogs + old aloof cat Tanner.

5 out of 5 average rating, 30 reviews

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.

Apartment in Madison

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.