Rutland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Rutland vacation deals
Price found within the past 48 hours. Click for updated prices.
- Level Chicago - River North
Sept 4 - Sept 7Level Chicago - River North + Flight
Downtown Chicago3 nights4.0 star property9.2/10 - Wonderful (1,039 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,600CA $1,076found 1 day agoper traveller - Level Chicago Fulton Market
Sept 3 - Sept 7Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (535 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YYZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,989CA $1,330found 1 day agoper traveller - Pendry Chicago
Sept 27 - Oct 3Pendry Chicago + Flight
Downtown Chicago6 nights4.5 star property9.2/10 - Wonderful (1,144 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $3,537CA $2,414found 21 hours agoper traveller - Thompson Chicago, by Hyatt
Sept 27 - Oct 3Thompson Chicago, by Hyatt + Flight
Downtown Chicago6 nights4.5 star property9.2/10 - Wonderful (1,375 reviews)"The hotel is nice and the rooms are generally good, but they are not keeping up with maintenance. The plastic backboard of the bed was worn and ripped (and gross looking), and the AC was very intense and uncomfortable. Carpet and walls in halls need repair. In short, the hotel is not worth the cost."Reviewed July 20, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $2,724CA $1,962found 21 hours agoper traveller - The Peninsula Chicago
Sept 27 - Oct 3The Peninsula Chicago + Flight
Downtown Chicago6 nights5.0 star property9.8/10 - Exceptional (1,004 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $4,660CA $3,461found 22 hours agoper traveller
Rutland Hotel Deals
Sleep Inn & Suites Oregon - Madison
Sleep Inn & Suites Oregon - Madison2.5 star property
4.4 km from Rutland
9.4 out of 10, Exceptional, (439 reviews)
9.4/10
Exceptional
(439 reviews)
"Great location, as well as clean, quiet, restful. No complaints."
The price is CA $106
CA $106
CA $121 total
includes taxes & fees
Aug 12 - Aug 13
9.4 out of 10, Exceptional, (1,000 reviews)
9.4/10
Exceptional
(1,000 reviews)
"Very nice room and stay"
The price is CA $167
CA $167
CA $187 total
includes taxes & fees
Aug 9 - Aug 10
Quality Inn & Suites Stoughton - Madison South
Quality Inn & Suites Stoughton - Madison South2.5 star property
9.6 km from Rutland
8.8 out of 10, Excellent, (483 reviews)
8.8/10
Excellent
(483 reviews)
The price is CA $104
CA $104
CA $118 total
includes taxes & fees
Aug 12 - Aug 13
Baymont Inn & Suites by Wyndham Madison
Baymont Inn & Suites by Wyndham Madison2.5 star property
17.8 km from Rutland
7.2 out of 10, Good, (1,454 reviews)
7.2/10
Good
(1,454 reviews)
The price is CA $102
CA $102
CA $118 total
includes taxes & fees
Jul 29 - Jul 30
Holiday Inn Madison at The American Center by IHG
Holiday Inn Madison at The American Center by IHG3.0 star property
29.6 km from Rutland
8.6 out of 10, Excellent, (765 reviews)
8.6/10
Excellent
(765 reviews)
"The carpet is worn and really lumpy causing tripping hazards and making it hard to roll a bag. For the first time in many stays, we had to wait til exactly 4 p.m. to check in because housekeeping didn't have rooms ready.
The location is very convenient for visiting family in the area, but the price is getting to be a but much foe the actual quality of the hotel. Needs some updating."
The price is CA $104
CA $104
CA $120 total
includes taxes & fees
Aug 2 - Aug 3
Home2 Suites by Hilton Madison Central Alliant Energy Center
Home2 Suites by Hilton Madison Central Alliant Energy Center3.0 star property
18.3 km from Rutland
9.6 out of 10, Exceptional, (1,001 reviews)
9.6/10
Exceptional
(1,001 reviews)
The price is CA $185
CA $185
CA $214 total
includes taxes & fees
Aug 9 - Aug 10
9.4 out of 10, Exceptional, (1,048 reviews)
9.4/10
Exceptional
(1,048 reviews)
"The staff recommended a great restaurant and store to get some gift items. Everyone was very friendly and so helpful.
The best value motel on our trip!
Thank you for a lovely place to stay!"
The price is CA $129
CA $129
CA $148 total
includes taxes & fees
Aug 2 - Aug 3
Best Western Plus InnTowner Madison
Best Western Plus InnTowner Madison3.0 star property
22.4 km from Rutland
9.2 out of 10, Wonderful, (1,002 reviews)
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."
The price is CA $229
CA $229
CA $264 total
includes taxes & fees
Aug 5 - Aug 6
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.
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 $1,076 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.