Oliveto Vacations from $589

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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 Firenze

4 out of 5
Historic Centre of Florence
Price was $982, price is now $589 per person
$589
per person
Jan 10 - Jan 15
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
Close to train station and everything you need.

Reviewed on Nov 21, 2025

Hotel Regency

Hotel Regency

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,408, price is now $924 per person
$924
per person
Jan 10 - Jan 15
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (439 reviews)
Loved it! Great place and very convenient

Reviewed on Jul 4, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Price was $2,708, price is now $1,841 per person
$1,841
per person
Jan 3 - Jan 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.8/10 Exceptional! (467 reviews)
Nice property and staff.

Reviewed on Nov 13, 2025

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Price was $1,126, price is now $775 per person
$775
per person
Feb 10 - Feb 16
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (399 reviews)
Staff is wonderful and kind, very accommodating. We stayed here with a lot of family members for our wedding, we got a beautiful spacious suite with the best courtyard views. The rooms are so beautifully designed, the whole villa is just dreamy and true Tuscany. Breakfast is amazing with so many options and so fresh, so delicious! Service is great too. Overall cannot beat the location. We also held our wedding reception dinner here and the food and service and spaces we used were amazing. They even gave us complimentary bottle of champagne and homemade cookies in our room with a lovely note. Overall, we hope to be back!

Reviewed on Nov 25, 2025

Hotel Lungarno - Lungarno Collection

Hotel Lungarno - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,667, price is now $1,159 per person
$1,159
per person
Feb 7 - Feb 11
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (593 reviews)
Excellent location! Truly a 5 star hotel ! Great service, breakfast, and service . Bedrooms were clean! Bathrooms were excellent!

Reviewed on Nov 19, 2025

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Discover the most popular places to visit in Oliveto

Church of Santa Maria Assunta

After visiting Church of Santa Maria Assunta, make a plan to see the other sights and activities in Civitella in Val di Chiana. Discover the area's countryside and wineries.

Church of Santa Maria Assunta

Virgin Mary with Child

You can learn about the history of Civitella in Val di Chiana when you stop by Virgin Mary with Child. Discover the area's countryside and wineries.

Virgin Mary with Child

Memorial of the Massacre

You can learn about the history of Civitella in Val di Chiana with a visit to Memorial of the Massacre. Discover the area's countryside and wineries.

Memorial of the Massacre

What to do in Oliveto

Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

$23
per adult
Oil museum and oil mill in Tuscany: tour and tasting
Hand made Guitar Spaghetti

Private Cooking Class in Tuscany | Hand Made Pasta

$203
per adult
Private Cooking Class in Tuscany | Hand Made Pasta
See all activities in Oliveto

Oliveto Hotel Deals

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
$296 nightly
The price is $335 total per night from Dec 14 to Dec 15
$335 total
Dec 14 - Dec 15
Total with taxes and fees
9.8/10 Exceptional! (254 reviews)
Our arrival experience was less than stellar for a warm welcome to property. Front desk associate was very cold and accusatory of the situation we encountered outside of the property. We have traveled extensively and I expected better arrival experience. It all changed for the better when we finally ...

Reviewed on Nov 23, 2025

Monastero di Cortona Hotel & Spa
Hotel Continentale

Hotel Continentale

4 out of 5
Piazza Guido Monaco, 7 Arezzo AR
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $142 total per night from Dec 3 to Dec 4
$142 total
Dec 3 - Dec 4
Total with taxes and fees
8.4/10 Very Good! (451 reviews)
We had a last-minute stay there due to the train strike, and it was a great evening after all… The hotel was right there in the main Square plus near the train station. The staff was lovely and they have the most beautiful rooftop patio and bar. you have to check out.

Reviewed on Oct 17, 2025

Hotel Continentale
B&B Hotel Arezzo

B&B Hotel Arezzo

3 out of 5
Via Einstein, 4 Arezzo AR
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $93 total per night from Dec 15 to Dec 16
$93 total
Dec 15 - Dec 16
Total with taxes and fees
8.4/10 Very Good! (335 reviews)
Nice hotel.
Nice hotel. Well located near Arezzo.

Reviewed on Feb 1, 2025

B&B Hotel Arezzo
See all 5,021 properties in Oliveto
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 Oliveto Vacation Packages

Oliveto Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Max Temp Winter
45ºF
Max Temp Summer
80ºF
Top Sights
Civitella Longobard Castle, Church of Santa Maria Assunta and Buriano Bridge and Penna Natural Reserve

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Frequently asked questions

How much does an Oliveto vacation package cost?
You'll find cheap prices from $589 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.

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