Holiday houses in Lake Wingra

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Top-rated holiday rentals in Lake Wingra

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 666 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).

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Top Guest favourite

Yurt in Cambridge

4.98 out of 5 average rating, 266 reviews

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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Superhost

A view from the breakfast nook captures a sunset over Lake Mendota. The serene water reflects hues of orange and gold, while a grassy area and few remnants of snow are visible. A coffee maker and glass kettle rest on the windowsill, enhancing the cozy setting.

Guest suite in Waunakee

4.81 out of 5 average rating, 330 reviews

Private guest suite on beautiful Lake Mendota

Cozy guest suite/basement apartment with separate entrance for nature lovers. Lake and capitol views from breakfast nook with microwave and mini fridge and coffeemaker. Full kitchen coming fall 2025. Quiet, woodsy, neighborhood adjacent to Governor Nelson State Park. Completely painted and updated 7/25/24. Tiki level, pier, and kayaks for guest use. People love the views, the hot tub and woods. It is a 1929 cabin so many stairs, some indoor insects and limited space. Well behaved pets welcome!

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Top 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, 202 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.

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Top Guest favourite

Home in Madison

4.97 out of 5 average rating, 270 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).

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Guest favourite

An outdoor dining area is featured on the deck, consisting of a wooden table surrounded by black wicker chairs. A small potted plant adds a natural touch. The scenic view of the river, a bridge, and a private dock can be seen in the background.

Home in Monona

4.92 out of 5 average rating, 131 reviews

Madison Lakefront Oasis in the Heart of Madison

Enjoy all that Madison has to offer from this beautiful lakefront property. BRING YOUR BOAT, our private dock on Yahara River has 3 slips with access to both Lake Monona & Lake Waubesa. Central location offers multiple restaurants, shops & public boat launch all within walking distance. Breath-taking sunsets over the lake. Quick 5-10 minute commute to downtown Madison, UW-Campus, Hospitals, Alliant Energy & Sylvee, State Street, hundreds of other Madison attractions east or west side!

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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

4.97 out of 5 average rating, 658 reviews

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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Top Guest favourite

The open living area features a light-colored sectional sofa and a coffee table at its center. A dining table with wooden chairs is visible on one side, while a kitchen with modern appliances and green accents can be seen in the background. Natural light illuminates the space through large windows.

Apartment in Cross Plains

4.99 out of 5 average rating, 68 reviews

Historic Luxury Apartment

This luxury 2-bedroom 2nd floor apartment is nestled in a beautifully remodeled historic building originally built in 1860. Combining old-world charm with modern amenities, this apartment offers the perfect blend of comfort and convenience. Located right on the Main Street of Cross Plains, WI, just 25 min away from UW hospital and 35 minutes from downtown Madison. Perfect for families, professionals and anyone looking for a stylish, comfortable stay close to Madison, WI.

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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

4.88 out of 5 average rating, 107 reviews

Madison's First 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.

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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.

Apartment in Madison

4.98 out of 5 average rating, 54 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.

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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, 421 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, living room w/a comfortable queen size sofa bed, a 54”HDTV, a kitchenette (not a full kitchen) w/a dining room table, a mini-fridge, 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

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Top Guest favourite

Apartment in Madison

4.96 out of 5 average rating, 92 reviews

The Wilson I | Renovated Studio w/ Sleeping Nook

Located within The Wilson, this thoughtfully designed studio sits on the second floor near the front of the building for easier access. A renovated kitchen with dishwasher and updated bathroom add convenience, while the bed is tucked into a cozy enclave for a restful feel. Early-morning service activity from the alley may occasionally be heard. Second-floor walk-up and paid parking nearby.

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