Windsor Holidays from £660

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Your Windsor Holiday

Lock in a Windsor holiday package and prepare to experience the highlights of this city. Think about staying in the neighbourhood of Marquette, which is good for cycling, culture and fishing. You'll want to go sightseeing during your trip to Windsor. Find time for top attractions such as Pink Elephant, Sun Prairie Golf Course and Token Creek Park. Browse Expedia's extensive range of travel options and book your dream holiday to Windsor today.

Top Windsor Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Villa Inn Motel

Villa Inn Motel

2.5 out of 5
Price was £675, price is now £660 per person
£660
per person
9 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LON) to Madison (MSN)
6.2/10 (12 reviews)
Good motel for construction workers. Looking for a deal on a room

Reviewed on 9 Jul 2026

Baymont by Wyndham Whitewater

Baymont by Wyndham Whitewater

2.5 out of 5
Price was £740, price is now £680 per person
£680
per person
16 Sept - 20 Sept
found 1 day ago
Return direct flight included
London (LON) to Madison (MSN)
7.4/10 Good! (770 reviews)

AmericInn by Wyndham Jefferson

AmericInn by Wyndham Jefferson

3 out of 5
Price was £745, price is now £697 per person
£697
per person
16 Sept - 20 Sept
found 1 day ago
Return direct flight included
London (LON) to Madison (MSN)
8/10 Very good! (488 reviews)
Location was good, across from Walmart. Fast friendly check in and out. Rooms were clean and modern. Newly remodeled. Great place to stay. Be mindful that they have no elevator so stay on ground floor if you don’t want to climb the stairs. The stairs were inside and well lit as well as wide

Reviewed on 2 Aug 2026

Fairview Inn & Suites Whitewater

Fairview Inn & Suites Whitewater

2 out of 5
Price was £805, price is now £761 per person
£761
per person
9 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LON) to Madison (MSN)
5.8/10 (53 reviews)
No hot breakfast just poptarts or pbj Advertised hot tub Toilet was messed up Bed/shower was comfortable

Reviewed on 28 Jul 2026

Fairfield Inn & Suites by Marriott Whitewater

Fairfield Inn & Suites by Marriott Whitewater

3 out of 5
Price was £948, price is now £921 per person
£921
per person
9 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LON) to Madison (MSN)
9.4/10 Exceptional! (437 reviews)

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)
Population
3,600
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC
Top Sights
Henry Vilas Zoo, Overture Centre for the Arts and Orpheum Theatre

Top hotels in Windsor

Days Inn by Wyndham Madison NE/Windsor

Days Inn by Wyndham Madison NE/Windsor

2 out of 5
6311 Rostad Dr Windsor WI
Fully refundableReserve now, pay when you stay
The price is £46 per night from 3 Sept to 4 Sept
£46
3 Sept - 4 Sept
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"I reserved a room for my 25 year old grandson and girl friend for four days starting July 30, 2026. On check-in they were given a room that was not clean, They complained and were given another room that also had a bad odor and seemed moldy, so they cancelled without occupying. I was charged one ..."

Reviewed on 4 Aug 2026

Days Inn by Wyndham Madison NE/Windsor
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is £102 per night from 9 Aug to 10 Aug
£102
9 Aug - 10 Aug
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is £53 per night from 3 Sept to 4 Sept
£53
3 Sept - 4 Sept
includes taxes & fees
Baymont by Wyndham Madison West/Middleton WI West
See all 413 properties in Windsor
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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All Inclusive Holidays
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Stay near popular Windsor attractions

Mousehouse Cheesehaus

9.0/10 (12 reviews)
Enjoy an outing to Mousehouse Cheesehaus during your stay in Windsor. Wander the area's lakeside or simply enjoy one of its top-notch restaurants.
See properties

What to do in Windsor

Downtown Madison Sightseeing & History with Self-Guided Audio Tour

Downtown Madison Sightseeing & History with Self-Guided Audio Tour

£8
per traveller
100% of travellers recommend
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
Madison: Haunts and Terrors Walking Tour

Murmurs of Mourning & Murder: Madison Ghost Tour

£18
per adult
Murmurs of Mourning & Murder: Madison Ghost Tour
Murmurs of Mourning & Murder: Madison Ghost Tour

Murmurs of Mourning & Murder: Madison Ghost Tour

£20
per adult
Murmurs of Mourning & Murder: Madison Ghost Tour
See all activities in Windsor

Frequently asked questions

How much does a Windsor travel package cost?
Get your credit card ready, because a trip to Windsor starts from just £660. When you bundle your flights, hotels and more into a travel package, you'll pick up the best deals.
If I'm not able to travel, can I cancel my Windsor travel package?
You can. We realise even the best-laid plans can go awry, so we're here to help if you have to make changes to your Windsor travel package. You may be able to cancel or amend your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.
How do I get a cheap travel package to Windsor?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all covered. Choose the combination that best fits you and see your savings grow. We know a package deal is never one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 properties across the globe, which lets you customize your Windsor adventure.
Does Expedia offer Book Now, Pay Later Windsor holidays?
Expedia has teamed up with online lender Klarna to make your next getaway easier on the purse strings. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more money to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find something that suits your budget. Consider these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's monthly instalment plans. If paying just a little each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Windsor?
If you're interested in visiting Mousehouse Cheesehaus, give commuting a miss and find a place to stay nearby. It's one of the top attractions in this neighbourhood.
What are the top hotels in Windsor?
Get your holiday off to a great start by booking a room at Motel 6 Madison, WI - East. It's one of most sought-after properties in Windsor. Another option is Hilton Madison Monona Terrace.
How far in advance should I book my Windsor holiday?
Be rewarded with the biggest variety at the cheapest prices by booking your adventure to Windsor early. Air carriers tend to release flight tickets anywhere up to 12 months in advance, so start locking things in as soon as you can. Having said that, Expedia is dedicated to providing you with the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Windsor travel package include?
Car rentals, hotels and flights — we bring you the best deals. All you have to do is pick your favourite combination. Once you've made your booking, you can add on the exciting stuff like activities and sightseeing tours. Our travel packages make it easy to create an exciting Windsor getaway.
What should I know before booking a Windsor travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and unlock great discounts. Hotels aren't your only choice, however. We've got beach villas, mountain cabins and even houseboats and castles!
Can I choose my airline with a Windsor Expedia travel package?
Yes, and with over 550 airlines to choose from globally, you're not short on choice. Look through the available options and see which airline best fits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.