Naples Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Find the Best Naples Vacation Packages

Naples Hotel Deals

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 ₩104,511 per night from Aug 31 to Sep 1
₩104,511
₩119,122 total
Aug 31 - Sep 1
includes taxes & fees
8.4/10 Very Good! (700 reviews)
"There is a strong odor of humidity in the hallway and the rooms."

Reviewed on Aug 24, 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 ₩117,277 per night from Sep 4 to Sep 5
₩117,277
₩133,673 total
Sep 4 - Sep 5
includes taxes & fees
Hampton Inn Jacksonville
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
The price is ₩118,462 per night from Aug 30 to Aug 31
₩118,462
₩130,285 total
Aug 30 - Aug 31
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 Aug 6, 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 vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation 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 vacation 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 travelers 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 vacation. 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 vacation package well in advance.
Is it cheaper to book a Naples vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays separately. Better still, you can personalize 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 vacation package to Naples?
If you've got your Naples vacation 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 favorite 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 vacation. 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 vacation package.

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