Windsor Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Windsor, Wisconsin, USA

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10.0 (1 Review)
3 Bedrooms 10 Guests
From GB £206 per night
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9.8 (9 Reviews)
1 Bedroom 2 Guests
10.0 (181 Reviews)
2 Bedrooms 4 Guests
From GB £44 per night
7.1 (422 Reviews)
83 Bedrooms 20 Guests
From GB £89 per night
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9.4 (1002 Reviews)
1 Bedroom 2 Guests
10.0 (71 Reviews)
1 Bedroom 2 Guests
New
1 Bedroom 10 Guests
9.4 (1000 Reviews)
1 Bedroom 2 Guests
10.0 (14 Reviews)
3 Bedrooms 10 Guests
From GB £118 per night
10.0 (1 Review)
1 Bedroom 2 Guests
10.0 (13 Reviews)
2 Bedrooms 12 Guests
From GB £172 per night
9.7 (3 Reviews)
1 Bedroom 3 Guests
10.0 (10 Reviews)
5 Bedrooms 20 Guests
From GB £165 per night
9.5 (2 Reviews)
1 Bedroom 4 Guests
From GB £104 per night
10.0 (1 Review)
1 Bedroom 2 Guests
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9.2 (59 Reviews)
117 Bedrooms 32 Guests
10.0 (1 Review)
2 Bedrooms 4 Guests
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9.1 (93 Reviews)
115 Bedrooms 16 Guests
From GB £165 per night
9.0 (5 Reviews)
1 Bedroom 5 Guests
9.8 (34 Reviews)
4 Bedrooms 12 Guests
From GB £117 per night
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8.9 (77 Reviews)
112 Bedrooms 29 Guests
9.8 (16 Reviews)
3 Bedrooms 10 Guests
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8.8 (77 Reviews)
88 Bedrooms 41 Guests
9.8 (7 Reviews)
4 Bedrooms 16 Guests
From GB £78 per night
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8.6 (299 Reviews)
225 Bedrooms 40 Guests
8.8 (36 Reviews)
1 Bedroom 2 Guests
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8.6 (182 Reviews)
13 Bedrooms 36 Guests
8.8 (21 Reviews)
2 Bedrooms 6 Guests
From GB £73 per night
8.5 (171 Reviews)
66 Bedrooms 32 Guests
From GB £93 per night
8.8 (15 Reviews)
1 Bedroom 3 Guests
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8.5 (132 Reviews)
139 Bedrooms 42 Guests
8.6 (7 Reviews)
1 Bedroom 2 Guests
8.5 (94 Reviews)
108 Bedrooms 36 Guests
8.4 (16 Reviews)
1 Bedroom 4 Guests
From GB £135 per night
8.5 (2 Reviews)
1 Bedroom 2 Guests
New
3 Bedrooms 8 Guests
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8.0 (106 Reviews)
121 Bedrooms 36 Guests
From GB £208 per night
New
1 Bedroom 2 Guests
7.4 (3 Reviews)
1 Bedroom 6 Guests
From GB £151 per night
8.0 (3 Reviews)
1 Bedroom 2 Guests
9.4 (685 Reviews)
1 Bedroom 2 Guests
6.8 (5 Reviews)
2 Bedrooms 4 Guests
From GB £80 per night
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7.8 (32 Reviews)
66 Bedrooms 32 Guests
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9.4 (346 Reviews)
1 Bedroom 2 Guests
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7.7 (779 Reviews)
111 Bedrooms 21 Guests
From GB £71 per night
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9.4 (63 Reviews)
1 Bedroom 2 Guests
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7.7 (206 Reviews)
271 Bedrooms 34 Guests
9.2 (1002 Reviews)
1 Bedroom 2 Guests
7.5 (30 Reviews)
124 Bedrooms 24 Guests
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9.0 (644 Reviews)
1 Bedroom 2 Guests
From GB £105 per night
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7.4 (275 Reviews)
194 Bedrooms 28 Guests
7.4 (128 Reviews)
53 Bedrooms 23 Guests
From GB £74 per night
6.9 (45 Reviews)
32 Bedrooms 22 Guests
From GB £56 per night
6.5 (378 Reviews)
82 Bedrooms 9 Guests
From GB £62 per night
6.1 (32 Reviews)
2 Bedrooms 6 Guests
5.5 (47 Reviews)
35 Bedrooms 17 Guests
From GB £143 per night
5.2 (150 Reviews)
84 Bedrooms 15 Guests
From GB £51 per night
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5.0 (534 Reviews)
91 Bedrooms 31 Guests
From GB £97 per night
5.0 (9 Reviews)
2 Bedrooms 3 Guests
From GB £58 per night
3.9 (125 Reviews)
6 Bedrooms 14 Guests
From GB £115 per night
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New
64 Bedrooms 10 Guests
From GB £115 per night
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New
148 Bedrooms 38 Guests
From GB £90 per night
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8.8 (1005 Reviews)
1 Bedroom 2 Guests
8.8 (925 Reviews)
1 Bedroom 2 Guests
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8.8 (585 Reviews)
1 Bedroom 2 Guests

About Windsor Vacation Rentals

With more than 122 Windsor vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Windsor.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windsor, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Windsor. Places to stay near Windsor are 446.06 ft² on average, with prices averaging GB £133 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Windsor with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Other Places to Stay in Windsor, WI


Frequently Asked Questions About Windsor?

What are the top vacation rentals in Windsor?

How many Rentbyowner vacation rentals are available in Windsor?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 122 in the Windsor area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windsor.