Rutland Vacations from $284
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The Latest Rutland vacation packages
Price found within the past 48 hours. Click for updated prices.
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
$510
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
7.8/10 Good! (575 reviews)
El lugar súper agradable y bueno lo recomiendo
Reviewed on Aug 31, 2026
Palazzo Lakeside Hotel
$382
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (5,311 reviews)
I've been thinking about staying here for awhile but was always a bit apprehensive. I finally took the plunge and glad I did. I checked in about 1:40pm and was offered a room for 35 early check-in fee (which I declined) I was told come back at 3 so went to eat. The hotel is 3 blds with breakfast in the third it has 5 floors. You must buzz to get in the big metal parking gate which at first seemed off putting but when you realize the blds do not require a key to enter it makes.sense. There is no shuttle to any parks included with the 29.99 resort fee so a car is needed . I will be staying here again. The breakfast had eggs, ham, pineapple, oranges, watermelon, bread to toast, 2 kind of cake, cereal, grits and make your own waffles. There was a kid's activity room that had 2 gaming devices (Minecraft and Roblox were in them) with couches. Second floor (above check-in) had washing machines/dryers and a dining area with tables and microwaves the pool area has cabanas and a big screen that was connected to Apple TV (it was showing avatar when I checked in) I noticed it was packed with people check-in around park closing time so that's something to consider. The hotel is honestly the best smelling hotel I've ever stayed.
Reviewed on Sep 1, 2026
Rutland Hotel Deals
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
$95 nightly
$102 total
Sep 23 - Sep 24
Total with taxes and fees
9.2/10 Wonderful! (1,484 reviews)
"Clean, nice, welcoming rooms and staff."
Reviewed on Sep 1, 2026
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
$105 nightly
$112 total
Sep 30 - Oct 1
Total with taxes and fees
Microtel Inn & Suites by Wyndham Lady Lake/The Villages
850 South US Hwy 27/441 Lady Lake FL
Fully refundableReserve now, pay when you stay
$75 nightly
$83 total
Sep 23 - Sep 24
Total with taxes and fees
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 $284 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.
