Bossi Vacations from ￥402,274
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Bossi Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel degli Orafi
Historic Centre of Florence
￥533,718
per person
Dec 27 - Jan 2
found 10 hours ago
Roundtrip flight included
Osaka (KIX) to Florence (FLR)
9.6/10 Exceptional! (1,005 reviews)
Everything was wonderful! Perfect location, beautiful rooms and the breakfast room looks like a museum with an incredible breakfast buffet. The staff couldn't have been more helpful. I watched the sunset from the rooftop bar and listened to opera coming from the plaza below. Fantastic experience!
Reviewed on Oct 24, 2026
Find the Best Bossi Vacation Packages
Bossi Hotel Deals
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
￥16,973
￥19,154 total
Nov 24 - Nov 25
includes taxes & fees
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
￥52,718
￥59,044 total
Nov 9 - Nov 10
includes taxes & fees
9.2/10 Wonderful! (643 reviews)
"Excellent location. Very nice service."
Reviewed on Oct 23, 2026
Hotel Chiusarelli
Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
￥14,569
￥16,553 total
Nov 17 - Nov 18
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Perfect in location, cleanliness,staff, amenities.... Wonderful 👍"
Reviewed on Oct 24, 2026
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.
What to do in Bossi
Pasta-making class at a Cesarina's home with tasting - Siena
￥32,252
per adult
Siena, San Gimignano, Monteriggioni & Chianti from Florence
￥11,712
per adult
88% of travellers recommend
Chianti: Lunch with Wine Tasting at Poggio ai Laghi Winery
￥6,306
per adult
Frequently asked questions
How much does a Bossi vacation package cost?
You can pick up a vacation package to this popular destination from ￥402,274 on Expedia. But how much your vacation to Bossi costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Bossi?
The off-season is the best time to travel to Bossi if you're hoping to keep costs down. Another tip for getting cheap Bossi vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Bossi?
With a well-organized schedule, you can easily visit the most popular Bossi attractions in a few days. But if you'd like to venture off the beaten track or go on day tours, consider booking your Bossi vacation for longer.
How to find the best Bossi package deals?
Finding a cheap Bossi package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Bossi package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Bossi vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging accommodations and flights separately. Better still, you can personalize your Bossi getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Bossi?
If you've got your Bossi travel dates locked in, book as soon as you can to snap up some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Bossi?
- Choose when to go: Check your schedule and get your bags packed. Your favorite time of year and the type of activities on offer will also help you decide when to vacation in Bossi.
- Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your hotel will likely be the largest expense during your trip to Bossi.
- Decide how many days away: Start by compiling a list of the activities and attractions you'd like to experience in Bossi. Then, estimate how long you'll need for each, as well as any travel time.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Bossi vacation package that brings all your bookings together.
Explore a world of travel with Expedia
- Inns in Nusenna
- Luxury Hotels in Villa
- Cheap Hotels in San Sano
- Siena Hotels
- Farmstay in Province of Siena
- B&B in Sogna
- Cheap Hotels in Siena City Centre
- Castles in Castellina in Chianti
- Boutique Hotels in Siena
- Aparthotels in Nusenna
- Winery Hotels in Radda in Chianti
- Vacation Homes in Siena
- Inns in Cavallari
- Radda in Chianti Hotels
- Boutique Hotels in Radda in Chianti
- Winery Hotels in Villa A Sesta
- Romantic Hotels in Chianti Region
- Rv Parks in Province of Siena
- Hotels with a Pool in Radda in Chianti
- Chalets in Chianti Region
- Hotels near Crete Senesi
- Villas in Siena
- Farmstay in Radda in Chianti
- San Sano Hotels
- Farmstay in Badia Agnano
- Country Houses in Vertine
- Rv Parks in Siena Station
- Condo Resorts in Radda in Chianti
- Town Houses in Castelnuovo Berardenga
- Resorts & Hotels with Spas in Radda in Chianti
- Hotels near Piazza del Campo
- Hotels with Free Parking in Siena Historical Center
- Romantic Hotels in Radda in Chianti
- Hotel Wedding Venues Hotels in Radda in Chianti
- Palaces in Radda in Chianti
- Apartments in Province of Siena
- Guest Houses in Asciano
- Adventure Hotels in Radda in Chianti
- Inns in San Sano
- Luxury Hotels in San Felice
- Cheap Hotels in Radda in Chianti
- Shopping Hotels in Radda in Chianti
- Lodges in Radda in Chianti
- Beach Hotels in Chianti Region
- Historic Hotels in Siena
- Hotels with Free Parking in Chianti Region
- B&B in Siena
- Resorts in Fonterutoli
- Inns in Province of Siena
- Luxury Hotels in Radda in Chianti
- Resorts in Castelnuovo Berardenga
- Villas in Radda in Chianti
- Luxury Hotels in Siena
- Cheap Hotels in Chianti Region
- Apartments in Siena
- Town Houses in Pianella
- Inns in Radda in Chianti
- Boutique Hotels in Casetta
- Hostels in Siena
- Castles in Radda in Chianti
- Castles in Montegrossi
- Hotel with a Concierge Hotels in San Sano
- All-Inclusive Hotel Hotels in Siena
- Luxury Hotels in Castellina in Chianti
- Aparthotels in Radda in Chianti
- Historic Hotels in Ponte A Bozzone
- Resorts in Villa
- Green Hotels in Radda in Chianti
- Ranches in Gaiole in Chianti
- Castles in Province of Siena
- Business Hotels in Radda in Chianti
- Cottages in Radda in Chianti
- Inns in Moncioni
- Guest Houses in Radda in Chianti
- Vacation Homes in Radda in Chianti
- Hotels near San Giovanni Terme Rapolano
- Resorts in Radda in Chianti
- Residences in Siena
- Inns in Ambra
- Luxury Hotels in Castelnuovo Berardenga
- Romantic Hotels in Siena
- Residences in Nusenna
- Palaces in Cavallari
- Apartments in Nusenna
- Farmstay in Chianti Region
- Beach Hotels in Radda in Chianti
- Resorts in Nusenna
- Resorts in Villa A Sesta
- Resorts in San Sano
- Winery Hotels in Siena
- Holiday Park Resorts in Radda in Chianti
- Resorts in Castellina in Chianti
- Farmstay in Asciano
- Hotels with smoking rooms in Siena City Centre
- Palaces in San Rocco a Pilli
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
