Rutland Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Rutland
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
€1,976
per person
9 Oct - 15 Oct
found 13 hours ago
Return direct flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (2,381 reviews)
The staff was very friendly and attentive and the hotel is in a great location, easy walk from the blue train
Reviewed on 7 Sept 2026
LIVN - Millennium Park Downtown Chicago
Downtown Chicago
€1,774
per person
9 Oct - 15 Oct
found 13 hours ago
Return direct flight included
Warsaw (WAW) to Chicago (ORD)
8.8/10 Excellent! (148 reviews)
Great location; easy check-in. Secure building with great amenities. Highly recommend!
Reviewed on 7 Sept 2026
Top hotels in Rutland
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
€118
20 Sept - 21 Sept
includes taxes & fees
9.4/10 Exceptional! (4,148 reviews)
"Excellent location. Staff helpful and friendly. Clean room. Comfortable beds. Restaurant was closed during our stay but we were able to order food from bar. Room service was excellent. You were able to hear a lot of noise in the hallway as door had a slight gap when closed."
Reviewed on 8 Sept 2026
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
€64
4 Oct - 5 Oct
includes taxes & fees
9/10 Wonderful! (1,322 reviews)
"Great hot tub"
Reviewed on 8 Sept 2026
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
€58
4 Oct - 5 Oct
includes taxes & fees
8/10 Very good! (1,472 reviews)
"It was as expected, nothing stood out. Good or bad.. it was worth the stay."
Reviewed on 8 Sept 2026
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 from €1,479 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?
- 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.
- 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.
- 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.
- 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.
