Vacation rentals in Windsor

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Top-rated holiday rentals in Windsor

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

Guest favourite
Cottage in Poynette
Lake Wiscosnin Cozy Cottage
Relax and unwind at this cozy cottage on the Wisconsin River with fantastic views. Enjoy the park right across the street with fishing, a picnic pavilion, beach and playground for your kids. Public boat launch is only a block away. Full laundry and eat in kitchen features quartz counter tops and makes you feel like you're home away from home. Many local restaurants and bars within driving distance, as well as wine tasting and 2 ski resorts. Keurig and a propane grill provided. CableTV and Wifi
20 – 27 Apr
4.97 out of 5 average rating, 187 reviews
Guest favourite
Home in Madison
Grooviest | Quiet | Close | NEW Upscale | 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 ;)
3 – 10 Nov
4.94 out of 5 average rating, 140 reviews
Guest favourite
Guest suite in Madison
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.
12 – 19 Apr
4.97 out of 5 average rating, 290 reviews

Popular amenities for Windsor holiday rentals

Other great holiday rentals in Windsor

Guest favourite
Home in Madison
Private apartment -2 Beds, Kitchen Office, Sunroom
4 – 11 June
4.88 out of 5 average rating, 206 reviews
Guest favourite
Home in Madison
Find Your Suite Here For a Sweet Price
27 June – 4 July
4.91 out of 5 average rating, 107 reviews
Guest favourite
Apartment in Madison
Private entry flat near Atwood neighborhood
15 – 22 Apr
4.96 out of 5 average rating, 100 reviews
Guest favourite
Townhouse in Madison
Quiet Eastside Madison Home
30 Jan – 6 Feb
4.93 out of 5 average rating, 254 reviews
Guest favourite
Guesthouse in Stoughton
Country cabin, birders paradise.
25 Sept – 2 Oct
4.94 out of 5 average rating, 325 reviews
Guest favourite
Tiny home in Darlington
Arbor Crest Cottage- Peaceful farm stay getaway.
25 Aug – 1 Sept
4.98 out of 5 average rating, 577 reviews
Guest favourite
Loft in Madison
Cape Cod Loft, High-Speed internet + King bed
17 – 24 Sept
4.88 out of 5 average rating, 361 reviews
Guest favourite
Cabin in Fox Lake
Cabin on the Trail
17 – 24 Oct
4.95 out of 5 average rating, 115 reviews
Guest favourite
Guest suite in Madison
DT+Bikes+Pvt Suite+Jacuzzi+Parking+Near Campus
28 Mar – 4 Apr
4.98 out of 5 average rating, 547 reviews
Superhost
Guest suite in Waunakee
Private guest suite on beautiful Lake Mendota
9 – 16 Nov
4.84 out of 5 average rating, 267 reviews
Guest favourite
Home in Windsor
3BR,1.5Ba half-duplex w/driveway near golf course
24 Nov – 1 Dec
4.8 out of 5 average rating, 80 reviews
Guest favourite
Apartment in DeForest
Downtown DeForest | *Walk to Parks*
18 – 25 July
5.0 out of 5 average rating, 40 reviews

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