Rutland Vacations from $420

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The Latest Rutland vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
Save 100% on your flight
Price was $724, price is now $420 per person
$420
per person
Nov 10 - Nov 16
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,002 reviews)
⭐️⭐️⭐️⭐️⭐️ Hotel Review: Hyatt Regency Deerfield I stayed at the Hyatt Regency Deerfield from Friday to Sunday, and it was truly a wonderful experience! The rooms were cozy, spotless, and very comfortable, making it easy to relax after a busy weekend. The staff was exceptional—warm, welcoming, and attentive in every interaction. The dining facility was excellent, with both the food and service exceeding expectations. After attending the John Legend concert, returning to the hotel felt like coming to a home away from home. Kudos to the entire team at Hyatt Regency Deerfield for making the stay memorable. I’ll definitely return and highly recommend this hotel!

Reviewed on Aug 25, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $838, price is now $456 per person
$456
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on Aug 26, 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $986, price is now $549 per person
$549
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,872 reviews)
Customer service amazing

Reviewed on Aug 24, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $989, price is now $552 per person
$552
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,825 reviews)
Staying here was nothing short of amazing thanks to this staff. They were very friendly, courteous and nice. Everyone was attentive and you can tell. They really loved working there and delivering service.

Reviewed on Aug 20, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $864, price is now $512 per person
$512
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
Right at the airport so it is convenient but it is old and needs updating

Reviewed on Aug 26, 2025

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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
$139 nightly
The price is $161 total per night from Aug 31 to Sep 1
$161 total
Aug 31 - Sep 1
Total with taxes and fees
9.4/10 Exceptional! (3,016 reviews)
"Governors Club access was definitely worth it. Staff were extremely friendly and helpful. Hotel was very quiet and clean. I only wish they had some outside sitting areas to be able to enjoy the amazing weather- but otherwise excellent. Very walkable as well to almost anything you wanted to do."

Reviewed on Aug 25, 2025

The Madison Concourse Hotel and Governor's Club
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

3 out of 5
516 Grand Canyon Dr, Madison, WI
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $94 total per night from Aug 31 to Sep 1
$94 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,189 reviews)
"Very clean with friendly staff."

Reviewed on Aug 23, 2025

AmericInn by Wyndham Madison West
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
$65 nightly
The price is $75 total per night from Sep 14 to Sep 15
$75 total
Sep 14 - Sep 15
Total with taxes and fees
7.8/10 Good! (1,009 reviews)
"Great value"

Reviewed on Aug 23, 2025

Baymont by Wyndham Madison West/Middleton WI West
See all 358 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.

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Frequently asked questions

How much does a Rutland vacation package cost?
You'll find cheap prices from $420 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.