Rutland Holidays from £910

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top Rutland Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,330, price is now £910 per person
£910
per person
1 Oct - 6 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.4/10 Very good! (2,037 reviews)
Perfect for a one night girls trip. Great location. Friendly staff.

Reviewed on 25 Jul 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,786, price is now £1,183 per person
£1,183
per person
26 Sept - 1 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Good hotel, I’m just not entirely sure if the amenities and overall experience justify the price. Other than big building, prime location and a nice looking hobby, the hotel doesn’t really offer any differential amenity to any random half-priced hotel a few blocks away.

Reviewed on 25 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,830, price is now £1,283 per person
£1,283
per person
26 Sept - 1 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (533 reviews)
Will be back great experience room was amazing.

Reviewed on 23 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,180, price is now £1,618 per person
£1,618
per person
26 Sept - 1 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,934 reviews)
Very good

Reviewed on 24 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £1,840, price is now £1,366 per person
£1,366
per person
13 Oct - 19 Oct
found 15 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (504 reviews)

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

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 £103 per night from 9 Aug to 10 Aug
£103
9 Aug - 10 Aug
includes taxes & fees
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 £66 per night from 11 Aug to 12 Aug
£66
11 Aug - 12 Aug
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 £60 per night from 24 Aug to 25 Aug
£60
24 Aug - 25 Aug
includes taxes & fees
Baymont by Wyndham Madison West/Middleton WI West
See all 371 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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 £910. 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.