A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windsor holiday rentals

A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

1. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (191 reviews)
"I loved the apartment hotel concept. Felt very homey and had a kitchen which was wonderful. Location was in a quiet neighborhood and underground parking was wonderful. Also enjoyed the keyless check in process. Staff was very responsive."
United States
Andrea
The price is £107
includes taxes & fees
1 Nov - 2 Nov
The Dylin
A chalkboard sign with a welcome message and room instructions.

2. 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, (24 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
The price is £446
includes taxes & fees
8 Oct - 9 Oct
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
A bedroom with a dark grey wall, a bed with a striped bedspread, multiple pillows, a small side table with a vase and a lamp, and two framed botanical prints on the wall.

3. Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
10.0 out of 10, Exceptional, (56 reviews)
"Great, comfortable stay. And close to shopping, which is just what I like to do! "
United States
Joyana A.
The price is £466
includes taxes & fees
11 Oct - 12 Oct
Capital City- 6 Miles from Madison with fireplace
An outdoor seating area with wicker furniture and a central fire feature.

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

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Madison
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and convenient! Everything went smooth."
United States
Thomas C.
The price is £204
includes taxes & fees
1 Nov - 2 Nov
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

5. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (56 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
The price is £269
includes taxes & fees
19 Oct - 20 Oct
2 Bed, 2 Bath Apartment at Cannery Square
Master Bedroom /King bed

6. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (24 reviews)
"Tami was a wonderful host! Check in was fast and she was easy to communicate with. The house was clean and spacious."
United States
Joanna C.
The price is £469
includes taxes & fees
11 Oct - 12 Oct
Entire 3 Bedroom with Fireplace - sleeps 12
A modern kitchen with a dishwasher, a dining area with a table and chairs, a living room with a sofa and a TV, and a ceiling fan.

7. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (30 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is £266
includes taxes & fees
8 Oct - 9 Oct
2 Bed, 2 Bath Apartment at Cannery Square
A modern kitchen with a refrigerator, microwave, and bar stools.

8. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (41 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 £305
includes taxes & fees
12 Oct - 13 Oct
2 Bedroom Apartment Downtown Sun Prairie!
A hotel room with a bed, a desk, a lamp, a framed picture, a kitchen area with cabinets and a microwave, and a carpeted floor.

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

Free Breakfast Pool & Hot Tub. Near East Towne Mall!
Madison
10.0 out of 10, Exceptional, (1 review)
"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."
United States
Joy E.
The price is £344
includes taxes & fees
1 Nov - 2 Nov
Free Breakfast Pool & Hot Tub. Near East Towne Mall!
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

10. 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
10.0 out of 10, Exceptional, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is £193
includes taxes & fees
11 Oct - 12 Oct
Escape to tranquility – your countryside haven, and at times with a horse or two
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

11. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is £203
includes taxes & fees
1 Nov - 2 Nov
Studio Apartment at Cannery Square
A gym with treadmills, elliptical machines, and free weights.

12. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very good, (16 reviews)
"Great little town to stay the night. Woke early 5:30 am to tow truck towing cars in front lot. We luckily parked in back lot as instructed. Other than the noise of this unfortunate event, we enjoyed our stay. Loved the town and many places to walk to. Pizza place was amazing!"
United States
Cheryl B.
The price is £210
includes taxes & fees
28 Oct - 29 Oct
Studio Apartment at Cannery Square
A spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

13. 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, (16 reviews)
"Beautiful place, great stay."
United States
Thomas D.
The price is £223
includes taxes & fees
25 Oct - 26 Oct
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
An outdoor patio with a brick grill and seating area.

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

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (6 reviews)
"Great place for a stay."
United States
Andy D.
The price is £135
includes taxes & fees
1 Nov - 2 Nov
King Suite | Free Breakfast. Pool and Hot Tub
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

15. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (55 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
The price is £103
includes taxes & fees
2 Nov - 3 Nov
A Room with a View
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

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

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (19 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is £333
includes taxes & fees
28 Oct - 29 Oct
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A hotel room with a bed, a desk, a lamp, a framed picture, a kitchen area with cabinets and a microwave, and a carpeted floor.

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

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
The price is £474
includes taxes & fees
19 Oct - 20 Oct
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

18. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is £187
includes taxes & fees
19 Oct - 20 Oct
Pool with Slide. Great for Business Travelers!
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

19. 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 £170
includes taxes & fees
11 Oct - 12 Oct
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A spacious dining area with a high ceiling and large windows, wooden furniture, and a view of the outdoors.

20. Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.6 out of 10, Exceptional, (30 reviews)
"Great Place Beautiful landscape from the deckHost was very responsive Would go back again in a heartbeat Everything you need for a great stay"
United States
John W.
The price is £326
includes taxes & fees
20 Oct - 21 Oct
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
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

DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

10/10 Excellent
"All staff were particularly helpful - front desk, restaurant and van drivers. Anxious to be sure my stay was exceptional."
John 3-night trip
Posted 1 hour ago
DoubleTree by Hilton Madison Downtown

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as £103 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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 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?

Doty ★ Walk to Everything -Hotel Quality- Downtown: This holiday home rental outside of Windsor is located in the city centre, and has a balcony, a selection of games and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Windsor?

With 3 Expedia holiday rentals, you're guaranteed 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 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.