Rutland Vacations from $284
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The Latest Rutland vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
$347
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
We waited at cocktail table in lobby bar over 20 min and No One came to our table to take bar order, left and tried go to roof top bar but iy was raining...short staffing, very few guest were at actual bar, dissapointing to not to be served or Noticed...we went next door to get drinks!
Reviewed on Oct 21, 2026
Rutland Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
$139 nightly
$161 total
Oct 25 - Oct 26
Total with taxes and fees
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
$69 nightly
$80 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (1,376 reviews)
"Very clean hotel. The staff were very nice and helpful. The breakfast was awesome! Will start again when we have to go back down to UW Madison hospital."
Reviewed on Oct 21, 2026
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
Fully refundable
$44 nightly
$51 total
Nov 8 - Nov 9
Total with taxes and fees
6.2/10 (1,052 reviews)
"There were fights on the property, people were loitering outside and inside the lobby. My neighbors from all directions partied all night and morning. AC is molded, bed smells like urine. Just an overall bad stay for me.."
Reviewed on Oct 21, 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.
Find the Best Rutland Vacation Packages
Rutland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Dane County Regional Airport (MSN) |
Population | 2,100 |
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Frequently asked questions
How much does a Rutland vacation package cost?
You'll find cheap prices from $284 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 vacation to Rutland costs.
What are the cheapest months to go to Rutland?
If you're looking to book a cheap Rutland vacation package, consider visiting in November, December and January. You'll generally find lower rates on airfares and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Rutland?
Typically, a handful of days is enough to tick off the top attractions during your Rutland vacation. But if you want to have time to unwind or take day trips, think about extending your trip.
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 vacation as a package?
You can enjoy significant savings on your Rutland retreat by booking a personalized vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Rutland vacation packages?
Set off on your perfect trip to Rutland with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or hold off until your next paycheck — we've teamed up with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
