Windsor Vacation Rentals from $135: Search Short-Term Rentals

Q: What's the top vacation rental that Windsor has to offer?

Paoli Den - Renovated Flat! : You might want to consider this vacation home rental near Windsor, which offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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In two weeks

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Our top choices for Windsor vacation rentals

1. Studio Apartment at Cannery Square

Sun Prairie

Cheryl B.

$247 nightly

Sep 4 - Sep 5

Total with taxes and fees

2. 2 Bed, 2 Bath Apartment at Cannery Square

Sun Prairie

Lisa V.

$319 nightly

Sep 3 - Sep 4

Total with taxes and fees

3. Studio Apartment at Cannery Square

Sun Prairie

$276 nightly

Sep 3 - Sep 4

Total with taxes and fees

4. 2 Bed, 2 Bath Apartment at Cannery Square

Sun Prairie

Angela C.

$361 nightly

Sep 20 - Sep 21

Total with taxes and fees

5. Escape to tranquility – your countryside haven, and at times with a horse or two

Dane

Katelyn F.

$227 nightly

Sep 7 - Sep 8

Total with taxes and fees

6. The Dylin

Downtown Madison

Seth

$142 nightly

Sep 7 - Sep 8

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

7. 2 Bedroom Apartment Downtown Sun Prairie!

Sun Prairie

Robert M.

$363 nightly

Sep 3 - Sep 4

Total with taxes and fees

8. Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

Madison

Thomas C.

$246 nightly

Sep 8 - Sep 9

Total with taxes and fees

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Top Windsor Hotel Reviews

Baymont by Wyndham Madison West/Middleton WI West

8/10 Good

"The hotel was clean. The staff was very kind and helpful. The bed was a little like a soup bowl, good thing it was a king and we had plenty of room! There were some interesting characters hanging around outside. We still felt safe, just noticed them."

Comfort Suites Madison West - Middleton

8/10 Good

"Except for check-in which was difficult (reviewed earlier), all staff were very nice. Breakfast great. Pub drinks were good and priced well except for Cabernet wine which tasted like vinegar. Also there were a couple of dripping vents in the ceiling of the lobby which dripped on you if you sat on the couches. Overall, very nice place for the money."

Moxy Madison Downtown

10/10 Excellent

"Great location for what we were in Madison for, very walkable area. Staff was friendly and helpful, got into room early which really helped us out. Room clean and nice lounge in the lobby. The restaurant on rooftop not open night we were there but very good Italian restaurant less than 1 block away. All in all a great experience"

La Quinta Inn & Suites by Wyndham Madison American Center

8/10 Good

"Very poor lighting in the bathroom and nowhere to hang more than 1 towel. Countertop was full of folded towels. Bathtub had mold stains and the shower floor was caved in and difficult to stand in. However, beds were comfortable and the breakfast was excellent."

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $135 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we give you a choice of vacation rentals in Windsor close to Mousehouse Cheesehaus, or you can go with a more remote option if you'd like a relaxing place to stay. Our travelers say Windsor has a good selection of restaurants. Make sure you have time to check out the shopping and sporting events during your trip.

What's the top vacation rental that Windsor has to offer?

Paoli Den - Renovated Flat!: You might want to consider this vacation home rental near Windsor, which offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Windsor?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Windsor stay.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Mousehouse Cheesehaus, or get out into nature at a spot like Olbrich Botanical Gardens. In the larger area, you’ll find East Towne Mall and Barrymore Theatre.

What are vacation rentals like in Windsor?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.

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Check prices for these dates

Our top choices for Windsor vacation rentals

1. Studio Apartment at Cannery Square

2. 2 Bed, 2 Bath Apartment at Cannery Square

3. Studio Apartment at Cannery Square

4. 2 Bed, 2 Bath Apartment at Cannery Square

5. Escape to tranquility – your countryside haven, and at times with a horse or two

6. The Dylin

7. 2 Bedroom Apartment Downtown Sun Prairie!

8. Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

9. Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

10. Hot Tub - Game Room - 20 min to Capitol - Pets

11. Entire 3 Bedroom with Fireplace - sleeps 12

12. Capital City- 6 Miles from Madison with fireplace

13. Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

14. Accessible 1BR Suite | Free Daily Breakfast & Pool

15. King Suite | Free Breakfast. Pool and Hot Tub

16. Free Breakfast. Pool & Hot Tub. Near East Towne Mall!

17. Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

18. Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

19. A Room with a View

20. King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Find vacation rentals that suit your style

Top Windsor Hotel Reviews

Baymont by Wyndham Madison West/Middleton WI West

Tru by Hilton Madison West, WI

The Madison Concourse Hotel and Governor's Club

Best Western Premier Park Hotel

The Edgewater

Comfort Suites Madison West - Middleton

Moxy Madison Downtown

Lake Wisconsin Resort

La Quinta Inn & Suites by Wyndham Madison American Center

Find out more about Windsor

Frequently asked questions

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