Rutland Vacations from $336

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The Latest Rutland vacation packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $601, price is now $336 per person
$336
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
It felt very safe and was very clean. The stuff was all ver nice and helpful. The area was nice to walk on the pier but if wanting to do anything downtown it required a lot of uber using.

Reviewed on Oct 12, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $723, price is now $403 per person
$403
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Healthy breakfast and very clean hotel with friendly staff.

Reviewed on Oct 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,162, price is now $656 per person
$656
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Very clean very nice hotel. Easy accesss to restaurants and shopping.

Reviewed on Oct 11, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $802, price is now $503 per person
$503
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on Oct 9, 2025

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $589, price is now $370 per person
$370
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (2,917 reviews)
Everything was great. It was awesome being back in Chicago again.

Reviewed on Oct 12, 2025

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Rutland Hotel Deals

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
$139 nightly
The price is $161 total per night from Oct 19 to Oct 20
$161 total
Oct 19 - Oct 20
Total with taxes and fees
9.4/10 Exceptional! (3,177 reviews)
"Didn’t workout."

Reviewed on Oct 6, 2025

The Madison Concourse Hotel and Governor's Club
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
$67 nightly
The price is $77 total per night from Oct 13 to Oct 14
$77 total
Oct 13 - Oct 14
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
"Over all a good stay and will be booking again, hopefully the hot tub will be up and running for the next stay"

Reviewed on Oct 5, 2025

Baymont by Wyndham Madison West/Middleton WI West
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
$79 nightly
The price is $91 total per night from Oct 19 to Oct 20
$91 total
Oct 19 - Oct 20
Total with taxes and fees
8.8/10 Excellent! (1,201 reviews)
"Great breakfast. Great location. Clean room."

Reviewed on Oct 9, 2025

AmericInn by Wyndham Madison West
See all 354 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.

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 $336 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.