Rutland Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to Rp173.195 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Rutland

The Waterfront Inn
The Waterfront Inn
3 out of 5
1105 Lake Shore Drive, The Villages, FL
9/10 Wonderful! (1,178 reviews)
"Great Lake view but could no longer fish or kayak due to HOA"

Reviewed on 13 Jul 2025

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The Waterfront Inn
Brownwood Hotel & Spa
Brownwood Hotel & Spa
3 out of 5
3003 Brownwood Blvd, Wildwood, FL
Fully refundableReserve now, pay when you stay
9.6/10 Exceptional! (1,011 reviews)
"We didn't expect such a beautiful Hotel in such a remote place. Well taken care, charming, enjoyable, staff was polite and attentive, beautiful pool with Cabanas, clean and fresh all around. High end furniture in room and throughout.."

Reviewed on 11 Jul 2025

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Brownwood Hotel & Spa
Holiday Inn Express & Suites Wildwood The Villages by IHG
Holiday Inn Express & Suites Wildwood The Villages by IHG
3.5 out of 5
928 East State Road 44, Wildwood, FL
Fully refundable
The price is Rp1.349.338 per night from 20 Jul to 21 Jul
Rp1.349.338
Rp1.443.726 total
20 Jul - 21 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Fabulous staff! Quiet and clean property. Beds are comfortable and breakfast is always amazing!"

Reviewed on 13 Jul 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,097 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.

Frequently asked questions

How much does a Rutland holiday package cost?
You'll find cheap prices on Expedia for your Rutland getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your holiday to Rutland costs.
What are the cheapest months to go to Rutland?
If you'd like to score a cheap Rutland holiday package, consider travelling in January, February and June. You'll usually find better rates on flights and accommodation during these months --- perfect for budget-conscious travellers.
How many days is enough for Rutland?
Usually, a handful of days is enough to see the top sights during your Rutland holiday. However, if you want to have some time to chill out or go on day tours, think about extending your itinerary.
How to find the best Rutland package deals?
Use Expedia's handy filters to help you 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 adventure for midweek, or search for Rutland package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Rutland holiday as a package?
You can enjoy significant savings on your next Rutland retreat by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Rutland?
Secure amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Rutland trip.
How to plan a trip to Rutland?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Rutland.
  2. Plan your budget wisely: In addition to the price of your hotel, you'll need to factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Rutland.
  3. Decide how long to go away for: Now that you're up to speed on Rutland, you can work out the right length of your holiday. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Rutland holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.