Oliveto Vacations from $839

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Your Oliveto Vacation

With all your travel needs organized before you go, our Oliveto vacation packages let you simply focus on vacationing! One place to base yourself in this vibrant city is San Pancrazio, which is great for culture and walking. Ready to explore your new surroundings? Civitella Longobard Castle, Virgin Mary with Child and Praetorian Palace are just three of the top-rated places to visit during your trip to Oliveto. Your dream Oliveto vacation is a few clicks away. Browse hotels, flights and more on Expedia for a trip that's tailored to suit your style.

The Latest Oliveto vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze
Aurum Uffizi
The Moon Boutique Hotel & Spa
LHP River Club
Hotel degli Orafi
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Oliveto Hotel Deals

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18, Castelnuovo Berardenga, SI
Fully refundableReserve now, pay when you stay
$394 nightly
The price is $445 total per night from Aug 30 to Aug 31
$445 total
Aug 30 - Aug 31
Total with taxes and fees
9.2/10 Wonderful! (181 reviews)
"Beautiful property, excellent service"

Reviewed on May 31, 2025

Borgo Scopeto Wine & Country Relais
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (246 reviews)
"Fabulous !! Not handicap friendly but everything else is perfect"

Reviewed on Aug 19, 2025

Castello di Spaltenna- Small Luxury Hotels of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
$336 nightly
The price is $379 total per night from Sep 1 to Sep 2
$379 total
Sep 1 - Sep 2
Total with taxes and fees
9.8/10 Exceptional! (230 reviews)
"Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect"

Reviewed on Aug 7, 2025

Monastero di Cortona Hotel & Spa
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.

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Frequently asked questions

How much does an Oliveto vacation package cost?
You'll find cheap prices from $839 on Expedia for your Oliveto getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Oliveto costs.
What are the cheapest months to go to Oliveto?
November, December and January are great times to look for cheap Oliveto vacation packages. Opting to travel in quieter months means you can usually find lower prices on flights and accommodations.
How many days is enough for Oliveto?
The ideal duration for your Oliveto vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to go to all the leading sights and discover some hidden gems along the way.
How to find the best Oliveto package deals?
Start your search for an Oliveto package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Oliveto package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oliveto getaway off to a flying start.
Is it cheaper to book an Oliveto vacation as a package?
You can enjoy significant savings on your Oliveto getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to view the best 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 Oliveto?
If you have your Oliveto travel dates locked in, book as early as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Oliveto vacation packages?
Secure your perfect escape to Oliveto with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snap up cheap deals while they last.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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