Rutland Vacations from $180

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The Latest Rutland vacation packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $306, price is now $180 per person
$180
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,178, price is now $538 per person
$538
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (1,075 reviews)
We love it there! The best

Reviewed on Nov 30, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $457, price is now $221 per person
$221
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $618, price is now $338 per person
$338
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience.

Reviewed on Dec 9, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $740, price is now $448 per person
$448
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

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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 lively breweries 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 Dec 14 to Dec 15
$161 total
Dec 14 - Dec 15
Total with taxes and fees
9.4/10 Exceptional! (3,372 reviews)
Everything was great!

Reviewed on Dec 9, 2025

The Madison Concourse Hotel and Governor's Club
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $78 total per night from Jan 9 to Jan 10
$78 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
Yes

Reviewed on Dec 10, 2025

Hampton Inn & Suites Madison-West
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
$106 nightly
The price is $122 total per night from Dec 14 to Dec 15
$122 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
I had a very comfortable stay! Hotel is conveniently only a 10 minute drive to and from MSN airport. The staff was friendly and my room was clean.

Reviewed on Dec 7, 2025

DoubleTree by Hilton Madison East
See all 364 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 $180 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.