Asciano Vacations from $1,222

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Your Asciano Vacation

Prepare to experience Asciano on your terms with a custom Asciano vacation package! Discovering the best parts of this lively city is easier with a base in a neighborhood such as Armaiolo, which is good for views, among many other things. You'll want to do a little exploring during your trip to Asciano. Carve out some time for big-name attractions such as San Giovanni Terme Rapolano, Terme Antica Querciolaia and Monte Oliveto Maggiore Abbey. Don't delay exploring this destination any longer. The perfect Asciano vacation is a few quick clicks away with Expedia.

The Latest Asciano 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 $1,691, price is now $1,222 per person
$1,222
per person
Aug 24 - Aug 29
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Bathroom has odd smells.

Reviewed on Jul 16, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,149, price is now $2,249 per person
$2,249
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (68 reviews)
Perfect location. Unmanned reception at night.

Reviewed on Jul 5, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,728, price is now $1,238 per person
$1,238
per person
Aug 24 - Aug 29
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Very centrally located. We enjoyed our stay and would recommend it. Only issue was you could smell the drains in room 203. They tried to get rid of the smell but couldn’t. Avoid this room and you will be fine.

Reviewed on Jul 15, 2026

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Price was $1,776, price is now $1,275 per person
$1,275
per person
Sep 28 - Oct 3
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.4/10 Very Good! (53 reviews)
Staff was helpful, the property was not very well maintained.

Reviewed on Jun 1, 2026

Bernini Palace

Bernini Palace

5 out of 5
Historic Centre of Florence
Price was $2,504, price is now $1,805 per person
$1,805
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (1,008 reviews)
Great hotel, we'll located at the heart of historic Florence. The staff is amazing, food is great, love it. Always stay here when I visit Florence. Thank you

Reviewed on Jul 15, 2026

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Stay near popular Asciano attractions

Monte Oliveto Maggiore Abbey

9.2/10 (12 reviews)
You can learn about the history of Asciano with a trip to Monte Oliveto Maggiore Abbey. Visit the area's spas, or simply enjoy its wineries.
See properties

What to do in Asciano

Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$51
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$74
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Seggiano: Guided Tour of the Olive Grove and Food Tasting

Seggiano: Guided Tour of the Olive Grove and Food Tasting

$29
per adult
Seggiano: Guided Tour of the Olive Grove and Food Tasting
See all activities in Asciano

Asciano Hotel Deals

Castello di Leonina Relais

Castello di Leonina Relais

4 out of 5
Strada Di Leonina 5 Asciano SI
$120 nightly
The price is $139 total per night from Jul 31 to Aug 1
$139 total
Jul 31 - Aug 1
Total with taxes and fees
9/10 Wonderful! (136 reviews)
"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. ..."

Reviewed on Jul 8, 2026

Castello di Leonina Relais
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
$514 nightly
The price is $572 total per night from Aug 15 to Aug 16
$572 total
Aug 15 - Aug 16
Total with taxes and fees
Precise Tale Poggio Alla Sala
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
$313 nightly
The price is $356 total per night from Aug 10 to Aug 11
$356 total
Aug 10 - Aug 11
Total with taxes and fees
9.2/10 Wonderful! (616 reviews)
"Gorgeous hotel, amazing views. Fabulous staff. They made our stay in Siena extra special."

Reviewed on Jul 15, 2026

Grand Hotel Continental Siena – Starhotels Collezione
See all 8,754 properties in Asciano
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 Asciano Vacation Packages

Asciano Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
4,100
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Pienza Cathedral, Terme Antica Querciolaia and Palazzo Piccolomini

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Frequently asked questions

How much does an Asciano vacation package cost?
You'll find cheap prices from $1,222 on Expedia for your Asciano escape. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Asciano costs.
What are the cheapest months to go to Asciano?
You can usually find reduced prices and greater availability in February, August and November. Take a look at our cheap Asciano vacation packages and you could get some great off-season discounts.
How many days is enough for Asciano?
Typically, a handful of days is enough to check out the top attractions during your Asciano vacation. But if you prefer to have some time to kick back or go on day trips, consider extending your itinerary.
How to find the best Asciano package deals?
Begin your search for an Asciano package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Asciano package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Asciano adventure underway.
Is it cheaper to book an Asciano vacation as a package?
You can enjoy significant savings on your Asciano break by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Asciano?
Land incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Asciano trip.
How to plan a trip to Asciano?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the activities available will also help you decide when to visit Asciano.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and dining out to experiences and flights. Your hotel will probably be the biggest expense during your trip to Asciano.
  3. Organize your Asciano getaway with our trip planning tool: Search for and book hotels and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Asciano together.
  4. Decide how long to go for: Now that you know more about Asciano, you can work out the right length of your vacation. Pull together a rough plan and allocate enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a tailored Asciano vacation package.
  6. Book any activities or excursions: Here's the fun part — locking in everything you want to see and do. Explore some of the top things to do in Asciano and book your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Asciano vacation packages?
Your Asciano break is meant to be an escape from your daily routine, not a reason for money-related stress. So to give you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.