Rutland Vacation Packages
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Top Rutland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,022
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
The Riu Plaza is more of a 2-3 star hotel staying there this week. Here are the reasons I experienced. Bed linen and towels dirty for 2 days having to be changed by cleaning staff. One bathroom sink stopped up. We visited the restaurant on the roof which had a nice ambiance but the service was extremely slow with the spicy wings I ate that did not agree with my stomach. Unfortunately there is no business center on the premises. The self-parking garage the hotel recommended is very scary.
Overall, we were highly disappointed with the 3 night stay at the Riu Plaza and do not recommend it.
Reviewed on Sep 6, 2026
Swissotel - Chicago
Downtown Chicago
CA $894
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,577 reviews)
First solo birthday trip and the staff was so accommodating! The room was very clean and comfortable. The location is the perfect spot to sightsee. The only downside was my iron didn’t work and the hallways were very hot.
Reviewed on Sep 5, 2026
Grand Geneva Resort & Spa
CA $1,063
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,009 reviews)
Our villa was clean and we had zero issues with it - everything worked. Laundry was easy to use, and we were even able to get room service. Somewhat unexpected given that the villas are detached from the main lodge. The only thing to know is that villas guests *do not* have access to the main outdoor pool, which means one cannot use the outdoor food/bar there. There is a small pool for each set of villas, but it is small, and minimally equipped. Again, no issues with it - perfectly nice, you just need to bring your own food.
Reviewed on Sep 4, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $988
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,685 reviews)
Arrived to a confusion about the room and pricing through Expedia. Staff was helpful and took care of it! Got the pricing we were promised and had a great stay! Me and my fiance had a great time!
Reviewed on Sep 5, 2026
Ready to book your vacation to Rutland?
Rutland Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
CA $165
CA $190 total
Sep 20 - Sep 21
includes taxes & fees
9.4/10 Exceptional! (4,135 reviews)
"Loved it."
Reviewed on Sep 5, 2026
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
CA $85
CA $98 total
Oct 4 - Oct 5
includes taxes & fees
AmericInn by Wyndham Madison West
516 Grand Canyon Dr Madison WI
Fully refundableReserve now, pay when you stay
CA $91
CA $105 total
Oct 4 - Oct 5
includes taxes & fees
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 CA $720 on Expedia for your Rutland break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Rutland costs.
What are the cheapest months to go to Rutland?
If you're looking to snag a cheap Rutland vacation package, consider travelling in January, February and November. You're likely to find better rates on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Rutland?
Generally, a handful of days is enough to explore the top attractions during your Rutland vacation. However, if you'd like to have some time to relax or go on day trips, think about extending your itinerary.
How to find the best Rutland package deals?
Use Expedia's handy filters to find some terrific Rutland package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Rutland package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Rutland vacation as a package?
You can enjoy significant savings on your next Rutland retreat by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to view some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Rutland?
Enjoy amazing discounts by booking your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Rutland break.
How to plan a trip to Rutland?
- Choose when to get away: Check your diary and get packing. Your preferred time of year and the activities available will also help you decide when to escape to Rutland.
- Budget wisely: In addition to the price of your hotel, you should factor in other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Rutland.
- Set the duration of your trip: Start by compiling a list of the activities and sights you'd like to get to in Rutland. Then, estimate how long you'll need at each, as well as any travel time.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Rutland vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
