Rutland Holidays

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    Save up to €900 when you book a flight and hotel together*

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Top Flight + Hotel Deals in Rutland

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,855, price is now €1,295 per person
€1,295
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)
Will be back great experience room was amazing.

Reviewed on 23 Jul 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €2,066, price is now €1,299 per person
€1,299
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €2,304, price is now €1,553 per person
€1,553
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9/10 Wonderful! (504 reviews)
We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure.

Reviewed on 23 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was €2,344, price is now €1,628 per person
€1,628
per person
6 Oct - 11 Oct
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)
Excellent location. My grandson (3.5 yeas old) and I thoroughly enjoy our daily routine of strolling along the lakeside, having meals, playing games, watching the fireworks and taking in the scenery. The room is clean and the staffs are nice. We spent a wonderful six-day vacation.

Reviewed on 24 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was €2,096, price is now €1,474 per person
€1,474
per person
6 Sept - 12 Sept
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.2/10 Wonderful! (1,035 reviews)
We had such a great stay! Only complaint was one of the blinds would not shut in one of the bedrooms, but we understood it was probably not fixable in the 2 days we were there. We were also upgraded to a better room upon arrival! Overall 10/10!

Reviewed on 23 Jul 2026

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
The price is €121 per night from 9 Aug to 10 Aug
€121
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 €70 per night from 23 Aug to 24 Aug
€70
23 Aug - 24 Aug
includes taxes & fees
Baymont by Wyndham Madison West/Middleton WI West
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is €141 per night from 2 Aug to 3 Aug
€141
2 Aug - 3 Aug
includes taxes & fees
Best Western Plus InnTowner Madison
See all 367 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 from €1,295 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.