Rutland Holidays
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- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Flight + Hotel Deals in Rutland
Price found within the past 48 hours. Click for updated prices.
Lifetime of Vacations Resort
€1,057
per person
29 Nov - 6 Dec
found 4 hours ago
Return direct flight included
Athens (ATH) to Orlando (MCO)
9.4/10 Exceptional! (178 reviews)
I had a very pleasant and relaxing seven-night stay at this resort. The unit was spacious, comfortable, and very well equipped, with a separate living room, a full kitchen stocked with dishes and appliances, and a very comfortable king-size bed. One of my favorite features was the beautiful lake view from the sliding glass door. The space was so peaceful and cozy that I actually spent much of my time just enjoying the unit itself rather than going out. That said, there are a few areas for improvement. First, the air conditioning system seemed to blow a fine black dust that accumulated on the living room table, so the filters or system may need maintenance. Second, there was no housekeeping service during my entire stay unless requested. For a seven-night visit, at least one basic cleaning would have been very helpful. I also appreciated having washers and dryers available in the buildings. The machines worked well and cleaned my clothes nicely. However, they are coin operated, which is inconvenient these days. I tried to get coins at the front desk, but they didn’t have any, and finding coins at nearby stores was surprisingly difficult. If the resort plans to keep coin-operated machines, having a change machine at the front desk would be extremely helpful. Even better, adding a card or digital payment option in the future. Overall, I really enjoyed my stay. With a few improvements in maintenance, housekeeping, and laundry convenience, the guest experience could be even better
Reviewed on 10 Sept 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
€1,716
per person
29 Nov - 4 Dec
found 3 hours ago
Return direct flight included
Athens (ATH) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
Pool was awesome.Villa was beautiful.
We couldn’t enjoy the waterpark because it was closed for most of our stay. I wish we would have known this before booking.
Reviewed on 11 Sept 2026
Top hotels in Rutland
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
€86
16 Sept - 17 Sept
includes taxes & fees
9.2/10 Wonderful! (1,497 reviews)
"Nice place and location. Staff friendly and helpful. Pool is awesome. Had a few ants crawling in room each day. Also refrigerator does not get cold."
Reviewed on 13 Sept 2026
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
€92
16 Sept - 17 Sept
includes taxes & fees
9.8/10 Exceptional! (1,404 reviews)
"The Brownwood is amazing and we will be back! The entire experience -- the staff, the decor, the room, the food, the pool -- all were top notch. Truly the only thing my husband and I could think of that would have made it better, would be to have a walk-up access to the bar. As it is, one must go ..."
Reviewed on 13 Sept 2026
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
€72
14 Sept - 15 Sept
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"Great staff especially the associate that checked me in."
Reviewed on 12 Sept 2026
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 from €1,057 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?
- 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.
- 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.
- 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.
- 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.
