Rutland Vacations from ₩903,104

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The Latest Rutland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ₩1,202,021, price is now ₩903,104 per person
₩903,104
per person
Sep 5 - Sep 7
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
8.2/10 Very Good! (2,854 reviews)
Front desk staff is very friendly and helpful. The room is a bit dated and small, layout is awkward. The TV doesn't work well. For a 4* hotel, I expect better quality toilet paper (it's the lowest grade). Sink doesn't drain quickly. I was stuck in Chicago due to flight cancellations so paid over $400 a night and it's surged pricing since all the airport hotels were out. Location is really convenient though.

Reviewed on Jul 22, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ₩1,410,644, price is now ₩980,322 per person
₩980,322
per person
Sep 5 - Sep 7
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
9.2/10 Wonderful! (1,035 reviews)
One of the best places we’ve ever stayed. We had an amazing view of downtown Chicago from our floor, and our executive suite was clean and comfortable. We thoroughly enjoyed our stay and would definitely come back. The customer service and our room were excellent.

Reviewed on Jul 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ₩1,522,873, price is now ₩1,068,148 per person
₩1,068,148
per person
Sep 5 - Sep 7
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
9/10 Wonderful! (501 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ₩1,685,350, price is now ₩1,249,784 per person
₩1,249,784
per person
Sep 5 - Sep 7
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
9.6/10 Exceptional! (1,934 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ₩1,388,532, price is now ₩1,061,204 per person
₩1,061,204
per person
Sep 5 - Sep 7
found 12 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)

Find the Best Rutland Vacation Packages

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
The price is ₩175,941 per night from Aug 9 to Aug 10
₩175,941
₩203,211 total
Aug 9 - Aug 10
includes taxes & 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
The price is ₩105,121 per night from Aug 9 to Aug 10
₩105,121
₩121,429 total
Aug 9 - Aug 10
includes taxes & fees
8/10 Very Good! (1,376 reviews)
"Room had an awful oder Lysol couldn’t get rid of…maybe shampoo carpet."

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
The price is ₩251,296 per night from Jul 31 to Aug 1
₩251,296
₩290,249 total
Jul 31 - Aug 1
includes taxes & fees
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.

Frequently asked questions

How much does a Rutland vacation package cost?
You'll find cheap prices from ₩903,104 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?
January, February and November are great times to search for cheap Rutland vacation packages. Choosing to travel in less busy periods means you'll typically find lower prices on flights and accommodations.
How many days is enough for Rutland?
The ideal duration of your Rutland vacation depends on what you'd like to do. Typically, a few days to a week will give you enough time to tick off all the top sights and discover some hidden treasures along the way.
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.
How to plan a trip to Rutland?

  1. Choose when to go: Check your diary and pack your bags. Your favorite time of year and the activities available will also help you decide when to vacation in Rutland.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and meals to activities and airfares. Your accommodations will probably be the largest expense during your trip to Rutland.
  3. Decide how long to go for: Now that you're more familiar with Rutland, you can work out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the perfect Rutland vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.