Rutland Vacations from $689

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The Latest Rutland vacation packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,119, price is now $689 per person
$689
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,913 reviews)
Always stay here when in Chicago!! Love it!

Reviewed on Jul 22, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,761, price is now $1,044 per person
$1,044
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
Clean Room, friendly staff, great breakfast, well organized.

Reviewed on Jul 22, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,490, price is now $930 per person
$930
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (523 reviews)

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 $1,652, price is now $1,044 per person
$1,044
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,627, price is now $1,038 per person
$1,038
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (501 reviews)

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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
$140 nightly
The price is $162 total per night from Aug 9 to Aug 10
$162 total
Aug 9 - Aug 10
Total with taxes and fees
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
$65 nightly
The price is $76 total per night from Jul 26 to Jul 27
$76 total
Jul 26 - Jul 27
Total with taxes and fees
8/10 Very Good! (1,377 reviews)
"This was a great value for the money. Good location and quiet. The front desk staff was also able to provide drinks since the bar/restaurant was being renovated at this location."

Reviewed on Jul 22, 2026

Baymont by Wyndham Madison West/Middleton WI West
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $177 total per night from Jul 31 to Aug 1
$177 total
Jul 31 - Aug 1
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"We really enjoyed our stay. Location was good for walking to Camp Randall. Restaurant was good, including the breakfast. Every employee was VERY friendly."

Reviewed on Jul 22, 2026

Best Western Plus InnTowner Madison
See all 367 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.

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 $689 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.