Rutland Holidays

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    Save up to €185 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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was €1,182, price is now €723 per person
€723
per person
13 Nov - 19 Nov
found 16 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,320, price is now €1,397 per person
€1,397
per person
13 Nov - 19 Nov
found 16 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on 29 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,734, price is now €1,057 per person
€1,057
per person
13 Nov - 19 Nov
found 16 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,489, price is now €975 per person
€975
per person
13 Nov - 19 Nov
found 16 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on 26 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,287, price is now €852 per person
€852
per person
13 Nov - 19 Nov
found 16 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

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
Get rates
The Madison Concourse Hotel and Governor's Club
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 €78 per night from 1 Sept to 2 Sept
€78
1 Sept - 2 Sept
includes taxes & fees
AmericInn by Wyndham Madison West
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 €65 per night from 14 Sept to 15 Sept
€65
14 Sept - 15 Sept
includes taxes & fees
Baymont by Wyndham Madison West/Middleton WI West
See all 356 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 €723 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.