
Holiday houses in Windsor
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Top-rated holiday rentals in Windsor
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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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Stay With Horses Escape Near Madison
Get ready for a quiet and peaceful stay. Take your pick: - 1King+1Queen Bed & 1 bath for 4 people - 1King+2Queen Beds & 2 baths for 6. (+$125 per night, contact host for payment) This home is attached to a barn with 6 Icelandic horses! Wake up to Icelandic horses just outside your window. A scenic escape with quiet mornings, fuzzy horses, and a one-of-a-kind IamGlytja experience - only 25 minutes from Madison - No horse riding allowed, owners to supervise all horse visits - No smoking / parties
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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.
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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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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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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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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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Haven on the Lake
Welcome to our unique A-Frame, Haven on the Lake! -1 hour from Madison -3 hours from Chicago -30 minutes from Cascade Mountain -40 minutes from WI Dells & Devil's Head Resort Nestled on a serene, five-acre lot overlooking Willams Lake, this renovated A-frame cabin is the perfect escape for families seeking peace, adventure, and natural beauty. The cabin offers a unique blend of modern amenities and old cabin charm, creating a cozy retreat in the heart of nature.
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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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Golf Course View Apartment
This unique place has a style all its own. Modern In-law Suite Apartment attached to our house located on beautiful Lake Windsor Country Club Golf Course, in Windsor WI. One bedroom with queen size bed, a full kitchen, bathroom, and washer/dryer. Two smart TVs, Wi-fi, and Cable TV. Private entrance and off-street parking with a gorgeous view of the golf course. Located 15 minutes from Madison, Sun Prairie, and Waunakee.
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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
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Private DeForest Flat| *Walk to Parks*
Welcome to our home! The upstairs flat of our home (built in 1904) has been recently updated. With a private entrance and lots of space for work or play, you and your family are sure to enjoy your stay with us. We are located in central DeForest, with easy walking access to groceries, restaurants and parks. Dane County Airport-16 min UW Madison- 29 min Devil's Lake-42 min Wisconsin Dells- 43 min
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Popular amenities for Windsor holiday rentals
Other great holiday rentals in Windsor

Dells Domes - Riverview Escape - Glamping Dome 4
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Private Resort Cabin | Pool • Hot Tub • Sauna
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Quiet, Peaceful A-Frame Chalet
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30 mins to capital and 45 mins to Devil’s lake
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Modern Riverview Cabin Near Devil’s Lake
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Historic guesthouse near UW
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Private Pool - Hot Tub - Sauna - Game Room - Pets
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Juniper Motel & Resort: King Cabin
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Destinations to explore
- Chicago Holiday rentals
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- Ann Arbor Holiday rentals
- Duluth Holiday rentals
- Wisconsin Dells Holiday rentals
- Grand Rapids Holiday rentals
- 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
- Kettle Moraine State Forest Lapham Peak Unit
- Blue Mound State Park
- Parfrey's Glen State Natural Area





