Rutland Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Rutland

Americas Best Value Inn Wenona

Americas Best Value Inn Wenona

2 out of 5
5 Cavalry Dr, Rutland, IL
Fully refundableReserve now, pay when you stay
The price is S$103 per night from 1 Sept to 2 Sept
S$103
1 Sept - 2 Sept
includes taxes & fees
7/10 Good! (312 reviews)
"This Property had bed bugs. When I went to the front desk they were not surprised and told me to leave. They said they would give me a refund but I booked through Expedia so we will see what happens now."

Reviewed on 13 Dec, 2024

Americas Best Value Inn Wenona
Days Inn by Wyndham Oglesby/ Starved Rock

Days Inn by Wyndham Oglesby/ Starved Rock

2 out of 5
120 N Lewis Ave, Oglesby, IL
Fully refundableReserve now, pay when you stay
The price is S$120 per night from 26 Aug to 27 Aug
S$120
26 Aug - 27 Aug
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Easy to check-in and reasonable fee for our dog. Staff quickly responded to our request for extra pillows because of our back issues."

Reviewed on 21 Aug, 2025

Days Inn by Wyndham Oglesby/ Starved Rock
Best Western Oglesby Inn

Best Western Oglesby Inn

2.5 out of 5
900 Holiday Street, Oglesby, IL
Fully refundableReserve now, pay when you stay
The price is S$155 per night from 25 Aug to 26 Aug
S$155
25 Aug - 26 Aug
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Clean and convenient."

Reviewed on 19 Aug, 2025

Best Western Oglesby Inn
See all 67 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?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Rutland costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Rutland?
February, March and November are great times to look for cheap Rutland holiday packages. Travelling in less busy months means you'll typically find lower prices on hotels and flights.
How many days is enough for Rutland?
With a well-planned schedule, you can easily visit the top Rutland sights in a few days. But if you want to discover hidden spots or go on day tours, think about booking your Rutland holiday for longer.
How to find the best Rutland package deals?
Bagging a cheap Rutland package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Rutland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Rutland holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Rutland holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Rutland?
If you're considering a spur-of-the-moment Rutland trip, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Rutland?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Rutland.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will probably be the largest expense during your trip to Rutland.
  3. Work out your trip length: Think about how long you'd like to spend discovering Rutland. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your accommodation and airfare: Once you've settled on your 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.