Rutland Holidays

  • Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Rutland Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago
Pendry Chicago
Level Chicago – Old Town
The Emily Hotel
Arlo Chicago
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Top hotels in Rutland

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
The price is S$173 per night from 1 Dec to 2 Dec
S$173
includes taxes & fees
1 Dec - 2 Dec
9.4/10 Exceptional! (2,104 reviews)
"Great customer service, clean, safe location."

Reviewed on 24 Nov,2024

The Madison Concourse Hotel and Governor's Club
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
The price is S$161 per night from 25 Nov to 26 Nov
S$161
includes taxes & fees
25 Nov - 26 Nov
9.2/10 Wonderful! (802 reviews)
"I arrived after dark so have rated the outsider grounds neutrally. The security provisions requiring cards for the elevator makes me feel more secure. Very clean and comfortable room!"

Reviewed on 21 Nov,2024

DoubleTree by Hilton Madison East
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
The price is S$168 per night from 8 Dec to 9 Dec
S$168
includes taxes & fees
8 Dec - 9 Dec
9/10 Wonderful! (1,005 reviews)
"Great gameday hotel!"

Reviewed on 23 Nov,2024

Best Western Plus InnTowner Madison
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 holiday package cost?
Be ready to book, because a getaway to Rutland starts from only S$757. When you bundle your hotels, flights and car rentals into a travel package, you’ll enjoy the biggest deals.
How do I get a cheap travel package to Rutland?
Booking a flight and hotel together with Expedia won’t just save valuable time — it’ll save you a pretty penny too. A Rutland holiday package makes it simple to organise the perfect trip. With more than 550 airlines worldwide to choose from, finding flights that fit your busy schedule won’t be hard. On top of that, we’ve got over 1,000,000 hotels globally to take your pick of. Now that’s what you call choice. No matter who you are, Expedia will help show you the world.
How far in advance should I book my Rutland holiday?
Browse Expedia to compare airfares ASAP. You can generally purchase a seat up to 12 months before departure. If it’s too early for your preferred air carrier, or you’re booking late, fear not. Cheap tickets to Rutland occasionally appear a few weeks before the date of departure.
What does an Expedia Rutland travel package include?
With Expedia, you can select a combination of flights, hotels and car rentals to create your perfect Rutland package. Once you’ve made your booking, you can add on fun stuff like tours and activities. Don’t forget — the more you bundle, the more you’ll save!
What should I know before booking a Rutland travel package?
A package can be easier on the bank balance than separately booking all you need for your adventure. For example, bundle your flights, hotels and rental cars and score big savings. No matter your holiday goals, there’s bound to be a package to suit your budget.
Can I choose my airline with a Rutland Expedia holiday package?
Yes — that’s the beauty of an Expedia holiday package. You get to choose. We have more than 550 airline partners all over the world, so you have options galore when creating your Rutland adventure.
If I'm not able to travel, can I cancel my Rutland holiday package?
Your situation can change in a flash, so yes. You may be able to change or cancel your Rutland holiday package at no cost within 24 hours of booking. For older bookings, you can still make the necessary changes, but your hotel, car rental company or airline may charge additional fees. Want more information? Have a look at our Customer Service Portal. We’ll help make sure your getaway goes off without a hitch.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.