Rutland Vacations from $475

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The Latest Rutland vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $779, price is now $475 per person
$475
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The place was beautiful. Breakfast was lovely and I enjoyed everything.

Reviewed on Apr 10, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,763, price is now $1,041 per person
$1,041
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
London House is in the perfect location directly across from the Chicago Riverwalk with easy walking access to many of the tourist attractions. Staff were so friendly and helpful! We thoroughly enjoyed our stay and plan to visit again.

Reviewed on Apr 10, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $906, price is now $547 per person
$547
per person
Jun 27 - Jun 30
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
Room was super clean. The view all the way down to the lake from balcony was nice.

Reviewed on Apr 2, 2026

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 $1,261, price is now $777 per person
$777
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay

Reviewed on Apr 7, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,347, price is now $859 per person
$859
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,357 reviews)
Everything was nice. Perfect

Reviewed on Apr 10, 2026

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Discover the most popular places to visit in Rutland

Legend at Bergamont

Enjoy a round of golf in Oregon at Legend at Bergamont. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Legend at Bergamont

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 Apr 12 to Apr 13
$161 total
Apr 12 - Apr 13
Total with taxes and fees
9.4/10 Exceptional! (3,628 reviews)
Nice location - quiet rooms. Convenient Starbucks inside the hotel. Only issue is the person who checked us in was a bit cranky - not welcoming at all.

Reviewed on Apr 11, 2026

The Madison Concourse Hotel and Governor's Club
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
$126 nightly
The price is $146 total per night from Apr 19 to Apr 20
$146 total
Apr 19 - Apr 20
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
Very nice breakfast and room very clean.

Reviewed on Apr 8, 2026

Best Western Plus InnTowner Madison
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $113 total per night from May 3 to May 4
$113 total
May 3 - May 4
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
Breakfast was very good. The food and drinks at the bar were good also. Hotel staff was very friendly and professional.

Reviewed on Apr 10, 2026

DoubleTree by Hilton Madison East
See all 368 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 $475 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.