Best Vacation Homes in Windsor
New
Apartment
7.4(3 Reviews)
1 Bedroom
2 Baths
6 Guests
Hot Tub
Breakfast
Parking
Pool
£158/Night
7 Nights - £1,104
Cabin
6.6(482 Reviews)
83 Bedrooms
4 Baths
20 Guests
292.42 ft²
- Parking
Balcony/Terrace
Air Conditioner
Internet
£49/Night
7 Nights - £346
House
9.8(9 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
Kitchen- Internet
£212/Night
7 Nights - £1,483
House
10.0(190 Reviews)
2 Bedrooms
1 Bath
4 Guests
1300 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£227/Night
7 Nights - £1,588
Hotel
9.5(2 Reviews)
1 Bath
355.21 ft²
- Parking
- Air Conditioner
- Internet
Child Friendly
£170/Night
7 Nights - £1,187
House
10.0(21 Reviews)
3 Bedrooms
2 Baths
10 Guests
2200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£450/Night
7 Nights - £3,148
Condo
10.0(20 Reviews)
3 Bedrooms
2 Baths
12 Guests
2000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
£484/Night
7 Nights - £3,390
House
10.0(16 Reviews)
5 Bedrooms
3 Baths
20 Guests
3040 ft²
Private Pool- Hot Tub
- Parking
- Pool
£562/Night
7 Nights - £3,934
Windsor Luxury Rentals
New
House
4 Bedrooms
3 Baths
16 Guests
3200 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
£608/Night
7 Nights - £4,259
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
3104 ft²
- Hot Tub
- Parking
- Pool
Ocean View
£483/Night
7 Nights - £3,378
Condo
9.8(48 Reviews)
4 Bedrooms
2 Baths
12 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£476/Night
7 Nights - £3,331
House
10.0(13 Reviews)
3 Bedrooms
3 Baths
12 Guests
3032 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£396/Night
7 Nights - £2,774
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
2566 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
£378/Night
7 Nights - £2,647
Condo
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
£346/Night
7 Nights - £2,424
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
£322/Night
7 Nights - £2,256
New
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
£293/Night
7 Nights - £2,049
Windsor Pet Friendly Vacation Rentals
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
Spa- Balcony/Terrace
- Kitchen
£137/Night
7 Nights - £962
Hotel
8.9(151 Reviews)
10 Baths
402.57 ft²
- Private Pool
Oceanfront- Hot Tub
- Parking
£142/Night
7 Nights - £992
Hotel
8.2(1425 Reviews)
1 Bath
- Hot Tub
- Parking
- Pool
- Kitchen
£61/Night
7 Nights - £427
House
10.0(1 Review)
2 Bedrooms
1 Bath
3 Guests
757 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
£115/Night
7 Nights - £808
Hotel
8.5(284 Reviews)
1 Bath
410.01 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
£86/Night
7 Nights - £600
Apartment
8.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Spa
- Balcony/Terrace
- Kitchen
£183/Night
7 Nights - £1,278
House
3 Bedrooms
1 Bath
6 Guests
1567 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£93/Night
7 Nights - £648
Apartment
1 Bedroom
1 Bath
3 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
£67/Night
7 Nights - £470
Windsor Large Vacation Homes
Condo
10.0(15 Reviews)
3 Bedrooms
3 Baths
10 Guests
3000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£521/Night
7 Nights - £3,648
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
14 Guests
2600 ft²
- Hot Tub
- Breakfast
- Parking
- Spa
£505/Night
7 Nights - £3,535
House
9.8(7 Reviews)
4 Bedrooms
2 Baths
16 Guests
1800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£239/Night
7 Nights - £1,670
Villa
7 Bedrooms
4 Baths
16 Guests
3500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
£812/Night
7 Nights - £5,686
£66/Night
7 Nights - £461
Why Choose Rent By Owner for your Windsor Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windsor
When should you plan your Vacation Rentals stay?
Timing your visit to this destination can enhance your experience, as each season offers unique opportunities for enjoying the local surroundings and atmosphere here in Windsor, Wisconsin.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy warmer temperatures and longer daylight hours, making it ideal for exploring the local area. The pleasant weather attracts visitors seeking outdoor activities and a lively atmosphere.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Early Fall (September to October)
This season offers mild weather and vibrant fall foliage that enhances the beauty of your surroundings. It’s the perfect time to experience the region's natural charm while avoiding peak summer crowds.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
With colder temperatures and less tourism, this time allows you to enjoy quieter accommodations and cozy indoor experiences in the area. It’s an advantageous season to find more affordable vacation rentals.
Average Temperature Daytime: 20-30°F - Nighttime: 0-15°F
Early Spring (March to April)
Before the busy summer season begins, this is when you can experience fewer crowds and the changing landscape. It’s an excellent opportunity for budget-conscious travelers to explore the region at a relaxed pace.
Average Temperature Daytime: 40-55°F - Nighttime: 25-35°F
Weekly Weather Forecast for Windsor
How to Book Your Windsor Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windsor
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a private patio or barbecue area, perfect for meals in the fresh air.
- Relax by a spacious, landscaped yard ideal for outdoor gatherings or playing with family and friends.
- Take advantage of a fire pit for cozy evenings and memorable nights under the stars.
- Make use of a swimming pool or access to nearby lakes for refreshing swims during your stay.
- Explore walking trails or bike paths right on the property or nearby, offering scenic excursions in the region.
- Benefit from well-maintained gardens or green spaces to enjoy peaceful outdoor relaxation.
- Utilize outdoor sports facilities like volleyball courts or basketball hoops often available at these properties.
Top Attractions Around Windsor
What attractions are nearby?
Enjoy a variety of outdoor activities, local dining, and cultural attractions just moments from your vacation rental in Windsor, Wisconsin, offering an authentic experience of this charming region.
Family Activities
- Windsor Historical Society Museum: Discover the local history and heritage of this region through engaging exhibits and historical artifacts.
- Lakeview Family Park: Enjoy outdoor family activities including playgrounds, picnic areas, and scenic walking trails along the waterfront.
- Riverfront Nature Center: Experience the region's natural beauty with educational programs and serene nature walks suitable for all ages.
- Windsor Community Farm: Introduce the little ones to farm life by participating in seasonal planting, petting animals, and learning about sustainable agriculture.
Adult Activities
- Visit the Wisconsin River: Enjoy scenic boat rides and fishing adventures along this prominent waterway that runs through the area.
- Explore Riverside Park: Relax or stroll through this picturesque park offering beautiful views, walking trails, and picnic spots perfect for leisure days.
- Discover local dining options: Savor regional flavors at charming restaurants that showcase the region's culinary heritage within the community.
- Attend community events: Experience local culture by participating in seasonal festivals and outdoor activities that bring residents and visitors together here.
Other Places to Stay in Windsor, WI
Mousehouse Cheesehaus
Windsor Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Attractions: Take advantage of the area's well-known attractions to immerse yourself in the local culture and create memorable experiences during your stay.
- Plan Outdoor Activities: The region offers scenic parks and outdoor spaces perfect for relaxing or engaging in activities like hiking or picnicking.
- Enjoy Authentic Dining: Savor the flavors of locally inspired restaurants that highlight the region’s culinary heritage.
- Book Early for Popular Rentals: Secure your preferred vacation rentals early to ensure a seamless and stress-free trip here, especially during peak seasons.
Transportation Options
- Personal Vehicle: Traveling by car offers the flexibility to explore the region at your own pace, especially convenient if you're staying in Windsor for a longer period.
- Local Bus Services: Public transportation options provide an affordable and eco-friendly way to navigate the area without the need for a rental vehicle.
- Taxi and Rideshare Services: Taxis and rideshare platforms like Uber or Lyft are readily available here, offering convenient door-to-door service around Windsor and nearby attractions.
- Bike Rentals: For a healthy and scenic option, bike rentals allow you to enjoy the area's natural beauty while traveling between key sites and accommodations.
Local Customs Options
- Traditional Wisconsin Greetings: When you visit, you'll notice that locals often greet each other with a warm handshake or friendly nod, reflecting the region's welcoming nature.
- Community Events and Festivals: Participating in local festivals is common here, where sharing food and folk music helps visitors connect with the area's cultural roots.
- Respect for Nature: The region values outdoor activities, so it's customary to show respect for natural spaces when exploring parks and trails nearby.
- Local Culinary Customs: Enjoying regional cuisine, such as locally sourced ingredients in traditional dishes, provides insight into the area’s culinary heritage during your stay.
Frequently Asked Questions About Windsor?
1. What are the top vacation rentals in Windsor?
There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor:
- A TOUCH OF COUNTRY LIVING Minutes from Madison
- Entire 3 Bedroom with Fireplace - sleeps 12
- Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
- Private Pool - Hot Tub - Sauna - Game Room - Pets
- Game Room - King Suite - Theatre Room - Fireplace
- 4 Bed, 3 Bath w/Pool, Hot Tub, Gym, Fire Pit on Lake Windsor Golf Course
- New and Modern 3-bedroom charming house 20 minutes from downtown Madison.
- 3-bedroom house in fabulous Sun Prairie with AC and charm
- Free Breakfast Pool & Hot Tub. Near East Towne Mall!
- Par-fect Escape on Lake Windsor Golf Course
2. How many vacation rentals have private pools in Windsor?
There are 14 vacation rentals with private pools near Windsor. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windsor are best for families?
If you are looking for a family-friendly vacation home in Windsor, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor:
4. How many Rentbyowner vacation rentals are available in Windsor?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 121 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.
5. What is the cancellation policy for vacation rentals in Windsor, Wisconsin?
Cancellation policies vary by listing, so it is best to review the specific property's terms before booking. You can find this information on the listing details or contact the owner directly for clarification.
6. How do I book a vacation rental in Windsor, Wisconsin, and what payment methods are accepted?
Booking is typically completed through the online platform's secure system, where you'll choose your dates and submit your payment. Accepted methods usually include credit cards, debit cards, and sometimes other digital payment options; details will be available during checkout.
7. Are there any hidden fees or additional costs when reserving a property in this region?
Additional costs, such as cleaning fees, service charges, or local taxes, are often itemized on the listing page before finalizing your reservation. Be sure to review all charges carefully to understand the total cost of your stay.
8. What amenities and features can I expect from vacation accommodations here?
Amenities vary by property but commonly include essentials like Wi-Fi, parking, and kitchen facilities. To ensure the rental meets your needs, review the detailed list of features provided in the listing description or contact the host directly.
9. How can I communicate with property owners or hosts in Windsor, Wisconsin, if I have questions?
You can reach out to hosts directly through the messaging platform of the booking site. They are available to answer any specific inquiries about the property, local area, or special requests before you confirm your reservation.
Windsor Top Rated Vacation Rentals
£91/Night
7 Nights - £639
Hotel
9.4(1001 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
£85/Night
7 Nights - £593
Hotel
9.4(717 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
£102/Night
7 Nights - £717
£138/Night
7 Nights - £965
Hotel
9.2(1005 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
£95/Night
7 Nights - £662
Hotel
9.2(100 Reviews)
1 Bath
288.47 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
£83/Night
7 Nights - £580
Hotel
9.2(59 Reviews)
1 Bath
301.39 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£185/Night
7 Nights - £1,297
£106/Night
7 Nights - £742
