Rutland Vacations from $289

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The Latest Rutland vacation packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
Westgate Vacation Villas Resort
Westgate Town Center Resort
Westgate Cocoa Beach Resort
Westgate Towers Resort
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Rutland Hotel Deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
$140 nightly
The price is $150 total per night from Jan 18 to Jan 19
$150 total
Jan 18 - Jan 19
Total with taxes and fees
9.2/10 Wonderful! (1,324 reviews)
Everything was great

Reviewed on Jan 12, 2026

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
$155 nightly
The price is $166 total per night from Jan 19 to Jan 20
$166 total
Jan 19 - Jan 20
Total with taxes and fees
9.6/10 Exceptional! (1,079 reviews)
Nice place we just didn’t eat breakfast

Reviewed on Jan 10, 2026

Brownwood Hotel & Spa
Hampton Inn & Suites Lady Lake/The Villages

Hampton Inn & Suites Lady Lake/The Villages

3 out of 5
11727 Ne 63 Rd Dr Lady Lake FL
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $122 total per night from Jan 25 to Jan 26
$122 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Clean, friendly, accommodating and great location

Reviewed on Jan 10, 2026

Hampton Inn & Suites Lady Lake/The Villages
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

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Frequently asked questions

How much does a Rutland vacation package cost?
You'll find cheap prices from $289 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 vacation to Rutland costs.
What are the cheapest months to go to Rutland?
June, July and October are great times to search for cheap Rutland vacation packages. Traveling in less busy periods means you can generally find reduced prices on hotels and flights.
How many days is enough for Rutland?
Typically, a handful of days is enough to explore the main attractions during your Rutland vacation. However, if you want to have more time to relax or take day tours, consider 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 vacation package as soon as possible.
Is it cheaper to book a Rutland vacation as a package?
You can enjoy significant savings on your next Rutland retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Rutland vacation packages?
Set off on your perfect escape to Rutland with our Book Now, Pay Later vacations. No need to save up or wait for payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snag great 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.