Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

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Guest favourite

Loft in Madison

4.88 out of 5 average rating, 369 reviews

Cape Cod Loft, High-Speed internet + King bed

Welcome! This property is on Madison’s funky-up & coming East side. Quiet, conveniently located residential neighborhood with great neighbors & free street parking. The upstairs unit is a private guest-dedicated suite with it's own kitchenette & side entrance. GPS: Meriter Hospital, St Mary's Hospital, UW Hospital- 15 min Dane County Airport- 7 min. Wisconsin State Capitol- 12 min. Ulbrich Botanical Garden's- 5 min. Camp Randall Stadium- 16 min. *Bike *Lyft *Uber *Nearby public bus stops

27 Sep – 4 Oct

$272 NZD per night

Guest favourite

Home in Madison

4.95 out of 5 average rating, 152 reviews

Grooviest | Quiet | Close | Upscale MCM | Records!

• ALL NEW RENOVATION, BRAND NEW LINENS, TOWELS, ETC • Two floor private home • Private backyard with patio & fire pits • Two TVs, one in living room, one in dining room • Luxury Mid Century Modern Stereo Console with records, bluetooth • Over 70 classic albums to listen to (jazz, rock, classical, eclectic) • Access to over 1000 classic albums at our downtown Music Studio • Electric fireplace with multi heat settings • Full Size Kitchen, Full Size Appliances, Fully stocked • Vintage Bar Cart ;)

11–18 Dec

$262 NZD per night

Guest favourite

Guest suite in Madison

4.97 out of 5 average rating, 295 reviews

Private & Clean Apartment Near Downtown & Airport

Private, sunny basement unit with separate entry accessible by keycode. 1 bedroom (queen), full bath, sitting area (2 twins/king bed), desk, WI-FI, TV, mini fridge, microwave, & coffee/tea. On street parking. Kid friendly! Note: We live with kids above the apartment - you will hear us walking around & some water pipes. 2-4 mi from Airport, Capitol, & UW Campus. Walk to brunch, pub, jazz lounge, bubble tea, grocery store, park, & bike path. Licensed by City & State. Paying all taxes & fees.

14–21 Aug

$171 NZD per night

Guest favourite

Guest suite in Madison

4.99 out of 5 average rating, 149 reviews

Peaceful 2 BR/1 BA w/ patio, firepit & pool table

• 1400 sq.ft. lower level suite • Private backyard with patio & gas fire pit • Two TVs • Electric fireplace • Pool and Air hockey table • Stocked kitchenette w/ bar seating area • Workspace • Blackout shades and curtains • Onsite parking in driveway for one vehicle • Ample street parking • 16-min drive to 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

30 Jun – 7 Jul

$291 NZD per night

Guest favourite

Home in Madison

4.94 out of 5 average rating, 278 reviews

Gorgeous Eastside Home+Yard+Bikes+5 Star Hosts

This 100 year old home is in the Town of Blooming Grove, an enclave completely surrounded by Madison's near eastside. It has been completely renovated and equipped with new heating & air conditioning. The house is sparkling clean with original hardwood floors, stairs & hardwood trim detail. There are 2 bedrooms, each with ample closet & storage space. The 1st floor has a living room, dining room, kitchen & bathroom. Please note the staircase is steep and may be difficult for some guests.

26 Apr – 3 May

$327 NZD per night

Guest favourite

Guest suite in Middleton

5.0 out of 5 average rating, 114 reviews

Quiet sunlit studio near vibrant downtown

This architect-designed studio is bathed in natural light, with two skylights and a breakfast nook with a wrap-around window. Featuring an upscale bathroom with 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 but has its own outdoor entrance and is soundproofed for privacy. Located just up the hill—a 5-minute walk—to Downtown Middleton and a 15-minute drive to UW and Downtown Madison.

23–30 Jul

$259 NZD per night

Guest favourite

Home in Madison

4.88 out of 5 average rating, 209 reviews

Private apartment -2 Beds, Kitchen Office, Sunroom

COVID CLEANED Private Garden Apartment. Feel at home in your private lower level living space. Our home is surrounded by beautiful landscaped gardens and patios. We are located near the lake, on the lake bike loop, in the heart of Madison. Relax outside, enjoy dinner on the patio or have a bonfire. Venture out on a bike ride to the farmer's market on the Capital Square, or visit Monona Terrace, State Street, Olbrich Gardens or the Alliant Energy Center; just a short distance away.

1–8 Aug

$291 NZD per night

Guest favourite

Home in Madison

4.99 out of 5 average rating, 300 reviews

Beautiful 3 Bedroom Apartment, Kitchen, Fireplace

Private lower level 1600sq ft apartment. Steps away from TPC Wisconsin! 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. Just a 5 min drive to the airport and close to downtown. TPC WISCONSIN OPENING 8/2023

30 Sep – 7 Oct

$332 NZD per night

Guest favourite

Guest suite in Sun Prairie

4.89 out of 5 average rating, 245 reviews

Entire Countryside Garden Suite, Peaceful Retreat

Welcome to our home! We have upgraded our Garden 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.

25 Jul – 1 Aug

$207 NZD per night

Guest favourite

Tiny home in Darlington

4.98 out of 5 average rating, 590 reviews

Arbor Crest Cottage- Peaceful farm stay getaway.

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. Our 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.

28 Sep – 5 Oct

$188 NZD per night

Guest favourite

Guesthouse in Sun Prairie

4.98 out of 5 average rating, 305 reviews

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!

2–9 Dec

$287 NZD per night

Guest favourite

Guesthouse in Stoughton

4.94 out of 5 average rating, 330 reviews

Country cabin, birders paradise.

Country cabin with small kitchen, SMALL BATHROOM, large porch, gardens and birds galore. Located in the country just south of Madison WI. Enjoy the country life, quiet yet close enough to the city to enjoy Madison's activities or Stoughton's Opera House. Sauna, Fire pit, hiking, ask about pets. WiFi is available but not reliable, this is a country setting with slow connections. Please communicate with me regarding pets before booking.

23–30 Mar

$176 NZD per night