Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Windsor vacation rentals

Terrace/patio

King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very Good, (5 reviews)
"Great place for a stay."
United States
Andy D.
The price is ￥20,302
￥26,776 total
includes taxes & fees
Jun 7 - Jun 8
King Suite | Free Breakfast. Pool and Hot Tub
Reception

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (147 reviews)
"nice location"
United States
Mary
The price is ￥20,565
￥23,753 total
includes taxes & fees
Jun 7 - Jun 8
The Dylin
Smart TV, computer monitors

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

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (6 reviews)
"This stay was truly perfect! Our hosts thought of every single detail and more. The property was perfectly appointed with all the little touches that made it ideal for a quiet couple's getaway just outside Madison. We drove nearly 8 hours north from Kansas City to get here, so imagine how wonderful it was to walk into a warm, cozy, welcoming house that had snacks on hand and a pizza delivery number front and center waiting for us! Best part of all - it was dog-friendly! Our dog immediately felt...
United States
Heather P.
The price is ￥21,457
￥36,796 total
includes taxes & fees
Jun 11 - Jun 12
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Dining

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful house! We loved the basement game room and found our stay very comfortable. "
United States
Anonymous traveler
The price is ￥43,973
￥83,852 total
includes taxes & fees
Jun 9 - Jun 10
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Outdoor dining

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (43 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
The price is ￥13,815
￥21,322 total
includes taxes & fees
Jun 9 - Jun 10
Enjoy Nature with Full Comfort!
Terrace/patio

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cozy Cabin on Crooked Lane close to Lake Wisconsin
Poynette
8.0 out of 10, Very Good, (2 reviews)
"Pet friendly cabin in the woods. Mostly updated and nice for 4-6 people. We stayed with our dogs and it worked well for us. "
United States
Jon A.
The price is ￥32,370
￥53,565 total
includes taxes & fees
Jul 6 - Jul 7
Cozy Cabin on Crooked Lane close to Lake Wisconsin
Fridge, microwave, oven, stovetop

2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (40 reviews)
"The host was very responsive and very kind and considerate to our reason for traveling. The property was beautiful and clean inside and out, we really enjoyed our stay."
United States
Sha'Vonne G.
The price is ￥30,861
￥65,302 total
includes taxes & fees
Jun 9 - Jun 10
2 Bedroom Apartment Downtown Sun Prairie!
Outdoor dining

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

Escape to tranquility – your countryside haven, and at times with a horse or two
Dane
The price is ￥22,226
￥37,636 total
includes taxes & fees
Jun 10 - Jun 11
Escape to tranquility – your countryside haven, and at times with a horse or two
Terrace/patio

Free Breakfast. Pool & Hot Tub. Near UW-Madison!

Free Breakfast. Pool & Hot Tub. Near UW-Madison!
Madison
The price is ￥34,740
￥45,473 total
includes taxes & fees
Jul 5 - Jul 6
Free Breakfast. Pool & Hot Tub. Near UW-Madison!
Exterior

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
The price is ￥15,830
￥37,528 total
includes taxes & fees
Jun 7 - Jun 8
Studio Apartment at Cannery Square
Outdoor spa tub

Private Pool - Hot Tub - Game Room - 20 min DT

Private Pool - Hot Tub - Game Room - 20 min DT
Sun Prairie
10.0 out of 10, Exceptional, (4 reviews)
"We had a great family weekend in a great home that had plenty of space for all 12 of us. It was clean and the host was very accommodating and responsive. We will definitely look to stay there again on our next ski adventure. "
United States
Kylie V.
Private Pool - Hot Tub - Game Room - 20 min DT
Pool

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

Private Pool - Hot Tub - Sauna - Game Room - Pets
Sun Prairie
10.0 out of 10, Exceptional, (14 reviews)
"Great place for large group gatherings. Communication with our host was amazing. Highly recommend."
United States
Anonymous traveler
Private Pool - Hot Tub - Sauna - Game Room - Pets
Interior

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

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Sun Prairie
10.0 out of 10, Exceptional, (16 reviews)
"Fantastic Stay!! Host was great to work with!"
United States
Heather H.
The price is ￥55,965
￥96,241 total
includes taxes & fees
Jun 7 - Jun 8
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Property grounds

Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.0 out of 10, Very Good, (13 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
Waters Edge Cottage
Smart TV, fireplace, stereo, printers

Premium 3BR | Near Trails + City

Premium 3BR | Near Trails + City
Fitchburg
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed staying here. VERY nice house, easy access, clean, a lot of space, no issues. We would book here again!"
United States
Liz A.
The price is ￥58,543
￥131,601 total
includes taxes & fees
Jun 7 - Jun 8
Premium 3BR | Near Trails + City
3 bedrooms, free WiFi, bed sheets

Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
9.8 out of 10, Exceptional, (18 reviews)
"This was the perfect size home for a holiday family get together. Nice common spaces with enough areas to go when a little alone time was needed "
United States
Steve S.
The price is ￥55,965
￥96,241 total
includes taxes & fees
Jun 7 - Jun 8
Entire 3 Bedroom with Fireplace - sleeps 12
Exterior

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

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Monona
9.8 out of 10, Exceptional, (52 reviews)
"The location is wonderful. The river setting is beautiful. The pelicans are so fun to watch. Enjoyed all the rooms with tvs."
United States
Robert
The price is ￥43,332
￥87,138 total
includes taxes & fees
Jun 8 - Jun 9
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Lobby

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

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
The price is ￥25,806
￥32,973 total
includes taxes & fees
Jun 29 - Jun 30
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
9.8 out of 10, Exceptional, (43 reviews)
"Absolutely would stay here again. Tami the host was wonderful, and very responsive. "
United States
Erika O.
The price is ￥59,963
￥101,099 total
includes taxes & fees
Jun 21 - Jun 22
Capital City- 6 Miles from Madison with fireplace
Fridge, microwave, oven, stovetop

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

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (13 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is ￥28,610
￥80,599 total
includes taxes & fees
Jun 9 - Jun 10
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
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

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"Great location and value! Room was surprisingly quiet given some construction works in the area and being across from the elevators. Long hallway in the room from the door to the living area helps. AC worked great."
Barry 4-night trip
Posted 4 hours ago
The Madison Concourse Hotel and Governor's Club

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
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

Amazing townhouse, amazing attractions, amazing city!: Visitors like this Windsor vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Madison Area Technical College.

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.