Rutland Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Rutland

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
9.4/10 Exceptional! (2,870 reviews)
"I liked the cleanliness"

Reviewed on 18 Jul, 2025

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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 S$100 per night from 15 Aug to 16 Aug
S$100
15 Aug - 16 Aug
includes taxes & fees
7.8/10 Good! (1,004 reviews)
Nice stay
"Have stayed several times for duration of multiple days and find it’s very comfortable. Great breakfast and coffee/tea/ cocoa is available all day in the lobby. Was surprised to see popcorn offered in the evening. I have only stayed on top floor which has been quiet. Management quickly took care ..."

Reviewed on 17 Jul, 2025

Baymont by Wyndham Madison West/Middleton WI West
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

3 out of 5
516 Grand Canyon Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is S$125 per night from 10 Aug to 11 Aug
S$125
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (1,155 reviews)
"I liked that there were no surprises. The breakfast was better than I remembered from my last two visits. The bed was super comfortable."

Reviewed on 16 Jul, 2025

AmericInn by Wyndham Madison West
See all 394 properties in Rutland
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.

Frequently asked questions

How much does a Rutland holiday package cost?
You'll find cheap prices on Expedia for your Rutland break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your holiday to Rutland costs.
What are the cheapest months to go to Rutland?
January, February and November are great times to search for cheap Rutland holiday packages. Choosing to travel in less busy periods means you'll typically find lower prices on flights and accommodation.
How many days is enough for Rutland?
The ideal duration of your Rutland holiday depends on what you'd like to do. Typically, a few days to a week will give you enough time to tick off all the top sights and discover some hidden treasures along the way.
How to find the best Rutland package deals?
Start your search for a Rutland package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Rutland package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Rutland getaway off to a flying start.
Is it cheaper to book a Rutland holiday as a package?
You can enjoy significant savings on your Rutland retreat by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to browse some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Rutland?
If you have your Rutland travel dates confirmed, book early to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Rutland?

  1. Choose when to go: Check your diary and pack your bags. Your favourite time of year and the activities available will also help you decide when to holiday in Rutland.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and meals to activities and airfares. Your accommodation will probably be the largest expense during your trip to Rutland.
  3. Decide how long to go for: Now that you're more familiar with Rutland, you can work out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your accommodation and airfare: Once you've settled on your trip dates and duration, book the perfect Rutland holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.