Rutland Holidays from £826
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 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 easyPackages with flights are ATOL protected
Top Rutland Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
£826
per person
25 Nov - 28 Nov
found 1 hour ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
We unfortunately came to stay when the staff decided to strike. No room service , no cleaning service for a 4 night stay. Barely got towels on the last day. Disappointing.
The only upside was the location.
Reviewed on 22 Oct 2026
Rutland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Dane County Regional Airport (MSN) |
Population | 2,100 |
Max Temp Winter | -3.89ºC |
Max Temp Summer | 24ºC |
Top hotels in Rutland
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
£102
25 Oct - 26 Oct
includes taxes & fees
9.4/10 Exceptional! (4,280 reviews)
"."
Reviewed on 23 Oct 2026
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
£59
2 Nov - 3 Nov
includes taxes & fees
9/10 Wonderful! (1,381 reviews)
"We stayed one night and was surprised at the quality compared to the low price. Everything was clean, comfortable and the staff were very pleasant. Good job everyone."
Reviewed on 23 Oct 2026
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
Fully refundable
£38
8 Nov - 9 Nov
includes taxes & fees
6.2/10 (1,055 reviews)
"The questions here are great ones... for pointing out this place's glaring inadequacies. Filthy hallways, torn curtains, a wall in the stairwell with a hole, security door that doesn't latch, etc. Well maintained? The ice machine was in pieces and those pieces were literally scattered around the ..."
Reviewed on 23 Oct 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 travel package cost?
We make it easy to travel the world, with Rutland travel packages starting from as low as £826. You'll have the flexibility to combine your favourite airlines, hotels and car rental. For the ultimate getaway, why not add some activities and tours to your itinerary?
If I'm not able to travel, can I cancel my Rutland travel package?
Don't worry if you're rethinking your Rutland travel package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We understand life can sometimes throw a spanner in the works, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to Rutland?
Just think of all the wonderful things you could do in Rutland with a wad of extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a Rutland travel package. You have loads of choice with Expedia too. In fact, you can choose from over 550 air carriers and 1,000,000 properties throughout the world. Whether you're taking a break with the family or travelling solo, planning a trip to Rutland is better with a package.
Does Expedia offer Book Now, Pay Later Rutland holidays?
Expedia has partnered with online lender Klarna to make your next trip a bit easier on the wallet. Paying by instalment means you can spread the costs of your next adventure, leaving you with more money to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find something that falls within your budget. Consider these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna can help. Paying in easy monthly instalments will make that dream getaway possible.
- Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
- Low deposit holidays: If paying a small percentage of your trip (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.
How far in advance should I book my Rutland holiday?
To land rock-bottom prices, book ASAP. Air carriers typically advertise flight tickets, along with some of the lowest fares, nearly 12 months ahead of time. Hotels, experiences and car rental should also be booked well in advance so you can have the pick of the bunch. If you've decided on a last-minute getaway to Rutland, there are always plenty of great deals on Expedia. Book your escape today!
What does an Expedia Rutland travel package include?
Expedia has everything you need to arrange your Rutland trip, but what goes into your package depends on you. Choose from a combination of flights, hotels and rental cars. After a few activities to fill in your time? Once you've made your booking, you can add them on too. No matter your style, there's a deal to match your needs.
What should I know before booking a Rutland travel package?
An Expedia travel package can be customized for your budget and is a simple way to make your money go further. How little or much you include is totally up to you. Hotels, rental cars and flights — choose any combination that suits your plans.
Can I choose my airline with a Rutland Expedia travel package?
With a travel package, you're the one in charge. Whether you're hoping to fly to Rutland in economy or business class, simply select from the available airline options. Expedia has access to more than 550 airline partners across the world.
* 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.
