
Holiday houses in Lake Wingra
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Top-rated holiday rentals in Lake Wingra
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YurtSimple
YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery
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Charming Campus Area Home • Entire Home Near UW
Steps to Camp Randall & an easy walk to UW–Madison! Spacious home for up to 10 guests with a comfortable layout, multiple bedrooms, full kitchen, and inviting gathering spaces. Enjoy the back patio—perfect for unwinding after a day on campus or exploring the city. Ideal for Badgers game weekends, family visits, and group stays. Please note: during football weekends, the host may use the garage and part of the driveway for tailgating; parking may be shared. Cleaning fee $150. No pets or smoking.
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Lake Monona Waterfront+HOT TUB+Game Room+EVCharger
🔹Lake Monona waterfront - easy access for fishing & boating 🔸Game room w/ pool table, PacMan, Centipede, 65” smart TV, board games, & bar 🔹King bed suite w/ 50" smartTV & walkout sliding door to the HOT TUB 🔸1 min drive to wine tasting, coffee, & restaurants 🔹2 min walk to Monona ice skating 🔸10min drive to downtown Madison & 15min to the airport 🔴You'll find "The Kohl Center, UW-Madison, Camp Randall Stadium, State Street, The Capitol, & The Alliant Energy Center" within 5 miles
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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.
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House on water! Near UW, Capital & Alliant Center
Enjoy a drink while sitting in the living room, looking out over Monona Bay & the Capital. What is better?--the view, or your proximity to downtown, UW campus, & the Alliant Center? Most mention the view. (Read some reviews!) Grill out and light the fire pit on the front lawn. Cross the street, and you're at the edge of Monona Bay. Parking is easy. Click “Show more” for things you might NOT like about the house: I'll be in the basement, pricing nuances, etc. Business travelers?--read on!
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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.
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Cottage Suite + Jacuzzi Bathtub & Sauna
This Suite is perfect for 1-5 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
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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.
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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).
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Downtown Lake Monona Haven | SUPs, Hot Tub & Sauna
Stay in your private 3BR, 2BA section of our lakefront home. Paddle from the dock, relax in the hot tub or sauna and enjoy mornings on the balcony with coffee. You’re moments from Willy Street restaurants and right on the bike path. Inside, find a full kitchen, comfy living spaces. Two parking spots included. Spend days on the water or exploring the city and evenings grilling or roasting marshmallows by the fire. Paddleboards included. Pontoon rental available in warmer months.
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Charming Milkhouse Cottage, minutes from Madison!
Welcome to The Milkhouse Cottage! Serving as an original milkhouse from the late 1800s on our pre-civil war farmhouse property, you will feel the timeless elegance of the original character and the beautiful french cottage decor. Perfect for couples, travelers, or business persons -- come and unwind in the scenic heartland countryside and rustic elegance, all with the convenience of location -- we are a quick 15 minute drive from the airport and all that Madison has to offer!
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Comfortable Madison Area Retreat In The Trees
Tri-level duplex centrally located in Fitchburg. Nestled in a quiet residential neighborhood backing up to a small patch of woods for privacy. Feel away from it all with the sights and sounds of nature yet close to all the modern conveniences. Enjoy separated living spaces, a fully equipped kitchen (per WI health code, edible cooking supplies are not allowed–we do provide untamperable salt and pepper), 3 bedrooms, 2 full bathrooms, fully stocked laundry room and attached garage!
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Popular amenities for Lake Wingra holiday rentals
Other great holiday rentals in Lake Wingra

Historic guesthouse near UW
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Cozy Garden Apartment Near it All!
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Hot tub with a wooded view
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Quiet, Peaceful A-Frame Chalet
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Juniper Motel & Resort: King Cabin
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Wonderful 3 bed home close to downtown & the lake
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Brittingham Cottage - Steps to the Beach -1.5 Bath
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Two Bedroom with Lake View
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Destinations to explore
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- Devil's Lake State Park
- House on the Rock
- Noah's Ark Waterpark
- Wisconsin State Capitol
- Lake Kegonsa State Park
- Mirror Lake State Park
- Glacier Canyon Lodge
- Wollersheim Winery & Distillery
- Cascade Mountain
- Governor Dodge State Park
- Henry Vilas Zoo
- Camp Randall Stadium
- American Players Theatre
- Chazen Museum of Art
- Tyrol Basin
- Overture Center For The Arts
- Dane County Farmers' Market
- Monona Terrace Community And Convention Center
- Madison Childrens Museum
- Ho-Chunk Gaming Wisconsin Dells
- Cave Of The Mounds Lowest Point
- Parfrey's Glen State Natural Area
- Blue Mound State Park
- Tommy Bartlett Exploratory





