Windsor Accommodations

New

Apartment

Apartment Suite Penthouse located at hotel on Madison's east side!

7.4

Very Good

(3 Reviews)

1 Bedroom 2 Baths 6 Guests

£158/Night 7 Nights - £1,106

View Deal

Cabin

Econo Lodge Madison East

6.6

Good

(482 Reviews)

83 Bedrooms 4 Baths 20 Guests 292.42 ft²

£49/Night 7 Nights - £346

View Deal

House

The Speckled Hen Inn B&B

9.8

Exceptional

(9 Reviews)

1 Bedroom 1 Bath

£212/Night 7 Nights - £1,485

View Deal

A TOUCH OF COUNTRY LIVING Minutes from Madison

Highly Rated

House

A TOUCH OF COUNTRY LIVING Minutes from Madison

10.0

Exceptional

(192 Reviews)

2 Bedrooms 1 Bath 4 Guests 1300 ft²

£226/Night 7 Nights - £1,582

View Deal

House

Entire 3 Bedroom with Fireplace - sleeps 12

10.0

Exceptional

(21 Reviews)

3 Bedrooms 2 Baths 10 Guests 2200 ft²

£450/Night 7 Nights - £3,152

View Deal

House

Private Pool - Hot Tub - Sauna - Game Room - Pets

10.0

Exceptional

(16 Reviews)

5 Bedrooms 3 Baths 20 Guests 3040 ft²

£563/Night 7 Nights - £3,939

View Deal

House

Game Room - King Suite - Theatre Room - Fireplace

10.0

Exceptional

(13 Reviews)

3 Bedrooms 3 Baths 12 Guests 3032 ft²

£397/Night 7 Nights - £2,777

View Deal

4 Bed, 3 Bath w/Pool, Hot Tub, Gym, Fire Pit on Lake Windsor Golf Course

Price Dropped

House

4 Bed, 3 Bath w/Pool, Hot Tub, Gym, Fire Pit on Lake Windsor Golf Course

10.0

Exceptional

(5 Reviews)

4 Bedrooms 3 Baths 10 Guests 3104 ft²

£483/Night 7 Nights - £3,383

View Deal

House

New and Modern 3-bedroom charming house 20 minutes from downtown Madison.

10.0

Exceptional

(3 Reviews)

3 Bedrooms 2 Baths 7 Guests

£100/Night 7 Nights - £703

View Deal

House

3-bedroom house in fabulous Sun Prairie with AC and charm

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 8 Guests 2566 ft²

£379/Night 7 Nights - £2,650

View Deal

House

Par-fect Escape on Lake Windsor Golf Course

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 8 Guests

£323/Night 7 Nights - £2,259

View Deal

Apartment

Cozy 1 Bedroom Apartment with King Bed & Patio Near Madison

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath 2 Guests

£137/Night 7 Nights - £960

View Deal

More Top-Rated Accommodations in Windsor Area

Why Choose Rent By Owner for your Windsor Accommodations?

What makes our Accommodations 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 Accommodations stay?

Choosing the optimal time to vacation here ensures you can enjoy the region's best weather and local events, making your stay truly memorable when booking accommodations through RentByOwner.com in Windsor, Wisconsin.

Peak Season Highlights

Late Spring to Early Summer (May to June)

During this period, you can enjoy pleasant weather that is ideal for exploring the area. The region experiences moderate temperatures, making it a comfortable time to stay in Windsor, Wisconsin.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F

Early Fall (September to October)

This season offers mild weather and beautiful fall foliage, perfect for outdoor activities. It's a popular time for visitors seeking a scenic escape in the region.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

Mid Winter (December to February)

The cold winter months bring fewer visitors, providing a peaceful retreat with lower rates. The region's landscape transforms into a quiet winter wonderland, ideal for those seeking tranquility.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 10°F to 15°F

Early Spring (March to April)

Before the height of the warmer months, this time sees fewer travelers as the weather transitions. It offers an opportunity to find more affordable accommodations while enjoying a quieter atmosphere.

Average Temperature Daytime: 40°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Windsor

How to Book Your Windsor Accommodations

What's our booking process?

Our platform allows you to browse a curated selection of accommodations. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Windsor

More Top-Rated Accommodations in Windsor Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations 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 options with picnic tables or patio setups to savor meals al fresco.
Take advantage of spacious yards or gardens for relaxing strolls or outdoor activities.
Make use of private or shared barbecue grills to elevate your outdoor cooking experience.
Benefit from easy access to nearby parks or green spaces ideal for outdoor recreation.
Relax on furnished patios, decks, or verandas that provide a perfect setting for unwinding outdoors.
Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
Access scenic views and serene surroundings that showcase the natural beauty of this region.

Top Attractions Around Windsor

What attractions are nearby?

During your stay, you can enjoy a variety of activities nearby, including exploring local parks and scenic trails, engaging in outdoor sports, or experiencing cultural attractions that showcase the charm of Windsor, Wisconsin, making it an ideal place to relax and unwind amidst natural beauty and regional heritage.

Family Activities

Windsor Park and Play Area You can enjoy outdoor fun at this park, offering playgrounds and picnic spots perfect for family outings in the region.
Madison Children's Museum This engaging museum provides interactive exhibits and hands-on activities that keep children entertained and learning during your stay nearby.
Henry Vilas Zoo A visit to this free zoo allows your family to see a variety of animals and enjoy educational programs within the local area.
Olbrich Botanical Gardens Explore beautiful gardens and outdoor spaces, ideal for relaxing strolls and family photo opportunities in this destination.

Adult Activities

Windsor River Walk Enjoy a leisurely stroll along the scenic river walk, perfect for relaxing and taking in the natural beauty of the area.
Local Wine Tasting Tours Discover regional wineries with guided tastings that showcase the area's renowned wine culture.
Golfing at Windsor Golf Course Play a round on the well-maintained greens at this local golf course, ideal for both beginners and experienced players.
Cultural Events at the Windsor Community Center Participate in events, classes, or exhibitions that highlight the vibrant arts scene in this destination.

Other Places to Stay in Windsor, WI

Mousehouse Cheesehaus

Explore 119 Properties

More Places to Stay Near Windsor

Windsor Travel Tips

How Can You Make the Most of Your Stay?

Plan ahead for outdoor activities: Take advantage of the area's beautiful natural scenery by scheduling outdoor pursuits early to maximize your experience in Windsor, Wisconsin.
Explore local dining options: Sampling regional cuisine can enhance your stay and offer a taste of this destination’s unique flavors.
Choose centrally located accommodations: Staying near key attractions or amenities ensures easy access to everything the region has to offer, making your visit more convenient.
Engage with the community: Connecting with locals can provide authentic insights and personalized tips to enrich your time here.

Transportation Options

Windsor Transit System This local transit service provides reliable bus routes throughout the area, making it easy to explore the region without a car.
Rental Car Services Numerous rental agencies in the vicinity offer convenient options for exploring Windsor and its surroundings at your own pace.
Taxi Services Reliable taxi companies operate here, offering door-to-door transportation for quick and comfortable travel within the region.
Bike Rentals For an eco-friendly option, consider bike rentals available nearby, allowing you to enjoy the scenic views of this destination at your leisure.

Local Customs Options

Local Festival Traditions: Celebrating community spirit, the region hosts annual festivals that showcase local arts, crafts, and cuisine unique to this destination.
Historical Greeting Etiquette: Visitors often observe respectful nods or handshakes when greeting locals, reflecting the area's appreciation for tradition and cordiality.
Community Dining Customs: Sharing meals at communal gatherings is a common practice here, emphasizing the importance of social bonds and local hospitality.
Seasonal Outdoor Activities: Engaging in outdoor customs such as seasonal festivals and recreational events allows visitors to experience the area's natural beauty and local culture firsthand.

Frequently Asked Questions about Windsor Accommodations

1. What are the top Accommodations 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 Accommodations in Windsor:

2. How many Accommodations are available in Windsor?

Currently, the total number of properties listed by RBO in 2026 is over 51 in the Windsor area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Windsor. 

3. What is the cancellation policy for accommodations in Windsor, Wisconsin?

The cancellation policy varies depending on the property listing. Please review the specific details on the individual property's page or contact the host directly to understand the terms and any applicable fees.

4. Are there any additional fees I should be aware of when booking here?

Additional fees such as cleaning fees, service charges, or local taxes may apply. These are detailed during the booking process or on the property listing, so it’s advisable to review these before confirming your reservation.

5. Is parking available at accommodations in Windsor, Wisconsin?

Most properties offer parking options, but availability and types vary. Check the listing details or contact the host to confirm parking arrangements suitable for your needs.

6. Can I modify my reservation after booking?

Reservation modification policies depend on the property owner. It’s recommended to reach out directly through the platform to discuss any changes to your booking and ensure they can be accommodated.

7. What amenities are typically included with stays in Windsor, Wisconsin?

Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, heating or air conditioning, and parking. Review each listing carefully to find accommodations that meet your preferences.