Naples Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 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 Naples

Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave, Jacksonville, IL
Fully refundableReserve now, pay when you stay
The price is S$110 per night from 28 Aug to 29 Aug
S$110
28 Aug - 29 Aug
includes taxes & fees
8.4/10 Very Good! (696 reviews)
"Everything was so clean and staff was very helpful. We have found a new motel to stay in Jacksonville, Il.."

Reviewed on 17 Aug, 2025

Best Western Jacksonville Inn
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave, Jacksonville, IL
Fully refundableReserve now, pay when you stay
The price is S$123 per night from 28 Aug to 29 Aug
S$123
28 Aug - 29 Aug
includes taxes & fees
8.6/10 Excellent! (471 reviews)
"Nice and quiet."

Reviewed on 18 Aug, 2025

Hampton Inn Jacksonville
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
The price is S$115 per night from 23 Aug to 24 Aug
S$115
23 Aug - 24 Aug
includes taxes & fees
9.2/10 Wonderful! (237 reviews)
"Always my Go-to place to stay in Pittsfield! Great staff, clean, comfortable, and location. Some rooms do not have windows so are really dark inside. But overall great place to stay!!"

Reviewed on 6 Aug, 2025

William Watson Hotel
See all 22 properties in Naples
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 Naples holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Naples costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Naples?
If you'd like to score a cheap Naples holiday package, consider planning a trip in January, February and November. You'll typically find lower prices on airfares and hotels during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Naples?
Typically, a handful of days is enough to see the major attractions during your Naples holiday. However, if you prefer to have time to unwind or take day trips, consider extending your trip.
How to find the best Naples package deals?
Use Expedia's filter tool to help you find some of the best Naples package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Naples 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 usually best to book your holiday package well in advance.
Is it cheaper to book a Naples holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and stays separately. Better still, you can personalise your Naples getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Naples?
If you've got your Naples holiday dates confirmed, book early to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Naples?

  1. Choose your dates: The things you want to do in Naples and your favourite season can help you decide when to travel.
  2. Set a budget: Consider costs such as flights, food and transportation when calculating how much to set aside for your trip to Naples. Then, pick a property that suits your budget, whether that's a wallet-friendly option or a high-end getaway.
  3. Decide how long to go away for: Now that you're more familiar with Naples, you can figure out the right length of your holiday. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Naples holiday package.

* 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.