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Windsor Holiday Rentals

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Holiday Rentals in Windsor

The Dylin by Mint House
Interior entrance

The Dylin by Mint House

4.0 star property
9.2 out of 10, Wonderful, (87)
"Nice, clean, well-equipped and well-decorated rooms. "
The Dylin by Mint House
Lake Wisconsin Resort
Exterior

Lake Wisconsin Resort

3.0 star property
10.0 out of 10, Exceptional, (1)
"The cabins looked small from the outside, but we're actually very spacious we didn't feel cramped everything was very clean there was a full kitchen a table big enough to sit at least four. I think the only thing that wasn't 100% perfect was the beds are a little small they were stiff and the pillows were also very small and serviceable. I would still definitely stay there again 100% and would recommend it to everyone!"
Lake Wisconsin Resort
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!
Outdoor spa tub

Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

9.8 out of 10, Exceptional, (243)
"The place is fully stocked and very clean. There was everything we needed and more. Host is amazing. The post talks about the beach down the road...don't bother, the beach in yard is perfect for pets or small children. Thank you for a great experience on our short time there. "
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!
Pool with Slide. Great for Business Travelers!
Lobby

Pool with Slide. Great for Business Travelers!

The price is HK$1,117
HK$1,446 total
includes taxes & fees
7 Sept - 8 Sept
Pool with Slide. Great for Business Travelers!
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Smart TV, music library, stereo

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

10.0 out of 10, Exceptional, (93)
"Such a charming spot right on the lake! Direct access to the water, beautiful views, close to a bunch of fun bars and restaurants, and an easy drive to Devil’s Lake, Wisconsin Dells, and Madison. We stayed for a long weekend with our six month old, and it was great! Joe, the owner, is so friendly and responsive. Highly recommended!"
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Doty ★ Walk to Everything -Hotel Quality- Downtown
Fridge, microwave, oven, stovetop

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (33)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Exterior

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

9.8 out of 10, Exceptional, (42)
"We enjoyed our stay!"
The price is HK$2,069
HK$4,190 total
includes taxes & fees
6 Oct - 7 Oct
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison
Interior

Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison

10.0 out of 10, Exceptional, (130)
"Clean, quiet neighborhood, and plenty of space for our whole crew during Ironman weekend. Would recommend for anyone visiting the Madison area. "
Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison
Capital PrimeTime - 6 Miles from Madison w/ fireplace
Exterior

Capital PrimeTime - 6 Miles from Madison w/ fireplace

10.0 out of 10, Exceptional, (26)
"Would recommend - very good location, nice space, and great host!"
The price is HK$2,925
HK$4,897 total
includes taxes & fees
16 Sept - 17 Sept
Capital PrimeTime - 6 Miles from Madison w/ fireplace
Paoli Den - Newly Remodeled!
Fridge, microwave, oven, stovetop

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (24)
"Prefect"
Paoli Den - Newly Remodeled!
ONE OF A KIND vacation rental with a view
Exterior

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (142)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!
Interior

Historic Home Near Wi Dells, Lake Wi & Party Space Avail!

8.2 out of 10, Very good, (20)
"Plenty of sleeping options for kids.Close to Devils Head.Many restaurants within a short drive."
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!
A Pleasant Retreat- No Cleaning Fee & New Discounts
Property grounds

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (247)
"Host was easy to communicate with and it was an overall a fantastic experience. "
A Pleasant Retreat- No Cleaning Fee & New Discounts
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Fridge, microwave, oven, stovetop

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

9.8 out of 10, Exceptional, (17)
"Enjoyed a wonderful stay."
The price is HK$1,313
HK$3,024 total
includes taxes & fees
22 Sept - 23 Sept
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Enjoy Nature with Full Comfort!
Outdoor dining

Enjoy Nature with Full Comfort!

9.4 out of 10, Exceptional, (30)
"Great location, beautiful, clean, and friendly host"
The price is HK$632
HK$996 total
includes taxes & fees
7 Sept - 8 Sept
Enjoy Nature with Full Comfort!
Contemporary home in quiet neighborhood with pool & great back yard close to all
Outdoor pool, a heated pool

Contemporary home in quiet neighborhood with pool & great back yard close to all

9.6 out of 10, Exceptional, (8)
"Sheila's clean home was fabulous and just what we needed. It was very spacious and accommodating for our family gathering of 10. The kids loved playing in the heated pool and yard. Checkout duties were fairly minimal and Sheila was very prompt and responsive through communication. We would certainly consider a return trip."
Contemporary home in quiet neighborhood with pool & great back yard close to all
Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!
Outdoor dining

Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!

9.8 out of 10, Exceptional, (88)
"This was a great place to stay for a weekend getaway with some friends. Would love to come by again in the summer time "
Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Interior

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

10.0 out of 10, Exceptional, (6)
The price is HK$2,574
HK$4,458 total
includes taxes & fees
16 Sept - 17 Sept
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Outdoor spa tub

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (116)
"My husband and I live hear Chicago and wanted a quick getaway and this beautiful apartment felt like a home away from home. The hosts thought of every detail when designing this fun and very functional space (even the shower soap was a special luxury!) The bed was incredibly comfortable and the fireplace added warmth and coziness. We would love to stay here again!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Madison & ~UW~-Madison Area Lakefront Home
Fridge, microwave, oven, stovetop

Madison & ~UW~-Madison Area Lakefront Home

10.0 out of 10, Exceptional, (195)
"The cottage is a great location, hiking trail, restaurants and pubs in walking distance, and short drive to Madison. It is well-furnished, comfortable and is located on the water with great views. My friends and I would highly recommend this property."
Madison & ~UW~-Madison Area Lakefront Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Find out more about Windsor

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
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Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Mousehouse Cheesehaus, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 are some of the best holiday rentals that Windsor has to offer?

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!: This holiday home rental outside of Windsor is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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 wider area, you’ll find East Towne Mall and Madison Area Technical College.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.