Vacation rentals in Lake Windsor

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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.

Par-fect Escape on Lake Windsor Golf Course

Relax and unwind at this cozy retreat on Lake Windsor Golf Course! Enjoy beautiful fairway views, a fully equipped kitchen, private patio, bar/rec room for entertaining and open living space perfect for families or couples. Thoughtful touches throughout — from fresh linens and high-speed Wi-Fi to smart TVs and a washer/dryer for longer stays. Close to Madison, dining, and shopping. Whether you’re here to golf, explore, or relax, this peaceful getaway offers comfort, convenience, and tranquility.

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.

Luxury Lakeside Oasis- 4 Bed / 3 Bath Lake Home

Enjoy time with your loved ones at our luxury lake front oasis. Breathtaking views combined with the ideal Middleton location & extensive updating make our home the perfect vacation destination. Huge windows maximize gorgeous views of 60+ feet of lake frontage. A fully updated kitchen boasts custom everything. Our home features: 4 bedrooms, 3 bathrooms, lofted office, open kitchen with an island & dining table. A short drive (5-7 mi) to UW Campus, Camp Randall, Kohl Center & Wi State Capitol

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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).

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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The Wilson Unit F | Handcrafted Downtown Retreat

Located within The Wilson, this tucked-away third-floor corner studio offers a charming downtown stay. Historic charm meets handcrafted warmth, with woodworking details and cozy design touches. The unit faces the empty lot and may occasionally experience trucks moving gravel. Guests enjoy the shared rooftop deck overlooking nearby restaurants and nightlife. Hosted by a local husband-and-wife team passionate about thoughtful spaces. Third-floor walk-up and paid parking nearby.

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Peaceful 2 BR/1 BA w/ patio, fireplace, pool table

• 1400 sq. ft. lower level suite • Private backyard with patio • Two TVs • Electric Fireplace • Pool table • Stocked kitchenette w/ bar seating area • Workspace • Blackout shades and curtains • On-site parking in the driveway for one vehicle • Ample street parking • 16-min drive to the UW campus and downtown • 9-min drive to the airport • 6-min drive to shopping and restaurants • Extremely safe neighborhood • License No. LICHMD-2022-00079 • Zone Permit ZTRHP1-2022-00005

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

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Beautiful 3 Bedroom Apartment, Kitchen, Fireplace

Private 3-bedroom lower level 1600sq ft apartment. Follow the path to the back of the main house, here you'll find a beautiful space with large windows and plenty of natural light. Enjoy the warm gas fireplace, large flat screen TV. Make meals in the generous farmhouse kitchen. Sorry no full-size oven. Relax on the paved patio overlooking the wetlands and listen to many birds. Steps away from TPC Wisconsin. Just a 5 min drive to the airport and close to downtown.

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Nothing Else Like It!

There is absolutely nothing else like it available, and you’ll agree as soon as you step foot inside! This beautifully designed home makes your stay comfortable with it's high end furnishings, bedding, towels, mattresses and dishes. Kick back and relax in this calm, stylish space. Fully fenced backyard great for dogs, entertaining and room for kids to play. Private work space available too! All bedrooms have room darkening shades!

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Prime Time - 3 Bedroom with Fireplace! Sleeps 12

Newly remodeled....3 levels, 3 bedrooms and an entire lower level with 2 queen beds and 75in TV. Access within a block to just about anything....restaurants, movie theater, gym, parks, pond, etc.... Large backyard, Fireplace for those cools nights.... 6 miles from downtown Madison. An Uber away! 30 min from Cascade Mountain for skiing, tubing hiking!! Devils Head Mountain/Lake is a short drive