Bossi Holidays from £335
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- Rest easyPackages with flights are ATOL protected
Your Bossi Holiday
Say farewell to planning worries and hello to a Bossi holiday package. With your travel details organised before you take off, you can focus on discovering this city, starting with Badia Coltibuono, which is good for families, nature and walking. You'll want to do some exploring during your trip to Bossi. Don't miss big-name attractions such as Siena Circuit, Chianti Sculpture Park and Piazza Marconi. Whoever you're going away with and whatever your budget, your ultimate Bossi holiday is only clicks away with Expedia.
Top Bossi Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
La Villa di STR
Siena Historical Center
£335
per person
3 Dec - 7 Dec
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (450 reviews)
We had a great stay at La Villa. We spent 4 days bicycling and our rental company was able to coordinate drop off and pick up without us needing to be involved. They had a storage area for our bikes. Location was away from the crowds but close enough to walk to all of the sites. Breakfast was excellent.
Reviewed on 13 Oct 2026
The Hoxton, Florence
Historic Centre of Florence
£625
per person
21 Nov - 28 Nov
found 1 day ago
Return flight included
Birmingham (BHX) to Florence (FLR)
9.4/10 Exceptional! (358 reviews)
We stayed at the Hoxton before we headed out to Tuscany for our wedding weekend. The staff was very accommodating and helpful, and the property itself was beautiful with a great location, it was a little bit more on the outskirts of the city center, which we are used to staying in when we travel to Florence, but we liked how quiet and secluded it was and the design of the property was really well done. We enjoyed the coffee bar downstairs and the Photo Booth in the lobby and the outdoor courtyard/bar area was a great meeting point for us and friends who were getting into town for wedding festivities.
We would recommend staying at the Hoxton and look forward to future stays in other cities and hopefully Florence again.
Reviewed on 13 Oct 2026
Hotel Certosa Di Maggiano
£660
per person
30 Nov - 5 Dec
found 1 day ago
Return direct flight included
London (LGW) to Florence (FLR)
10/10 Exceptional! (217 reviews)
Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc.
The property was beautiful, maintained nicely, and was very quiet.
Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!
Reviewed on 28 Sept 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
£538
per person
21 Nov - 28 Nov
found 1 day ago
Return flight included
Birmingham (BHX) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Great location! Staff was friendly and helpful. Had a wonderful stay Highly recommend!
Reviewed on 11 Oct 2026
Monastero di Cortona Hotel & Spa
Cortona Old Town
£507
per person
13 Dec - 18 Dec
found 6 hours ago
Return flight included
London (LGW) to Florence (FLR)
10/10 Exceptional! (337 reviews)
Frederico went above and beyond to transfer us to our villa and Giulio was a fantastic bartender
Reviewed on 13 Oct 2026
Bossi Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Max Temp Winter | 10ºC |
Max Temp Summer | 29ºC |
Top Sights | Castle of Brolio, Monteriggioni Castle and Castello di Albola |
Top hotels in Bossi
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
£97
13 Nov - 14 Nov
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Reception staff very friendly and helpful. Room on top floor had two full length windows with spectacular views. Older property but updated nicely; not modern but comfortable. Comfy bed, linens and pillows. Nice breakfast with lots of variety. There are two floors that have breakfast - the lowest ..."
Reviewed on 11 Oct 2026
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
£275
13 Nov - 14 Nov
includes taxes & fees
9.2/10 Wonderful! (638 reviews)
"Gorgeous hotel in the heart of historic Siena."
Reviewed on 13 Oct 2026
Hotel Chiusarelli
Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
£93
8 Nov - 9 Nov
includes taxes & fees
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
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
£16
per adult
Chianti Half Day Wine Tour from Florence
£21
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
£68
per adult
88% of travellers recommend
Frequently asked questions
How much does a Bossi travel package cost?
Get ready to book, because a getaway to Bossi starts from just £335. When you combine your hotels, flights and car rentals into a package, you'll land the best bargains.
If I'm not able to travel, can I cancel my Bossi travel package?
We totally understand that unexpected stuff happens. If you've booked a Bossi travel package and have to cancel or change it, we're here to help. We suggest checking out our Customer Service Portal first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or amend your itinerary at no cost. If it's been longer than 24 hours, your hotel, airline or car rental company may charge a fee.
How do I get a cheap travel package to Bossi?
Think of all the amazing things you could do in Bossi with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your flights and hotel into a Bossi holiday package. You have plenty of choice when you book your trip with Expedia too. In fact, you can choose from over 550 air carriers and 1,000,000 hotels around the globe. Whether you're heading off with the whole family or adventuring alone, exploring Bossi is better with a package.
Does Expedia offer Book Now, Pay Later Bossi holidays?
We sure do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply pick the payment plan that works for you during checkout and take the stress out of budgeting for your next trip. Remember to bundle your accommodation, car hire and flights with Expedia to get the biggest bang for your holiday buck. Take a look at our flexible payment options below:
- Pay monthly holidays: Escape on that dream holiday sooner with Klarna's monthly instalment plans. If paying just a small amount each month works for you, pick this option at checkout.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your holiday in multiple transactions.
- Low deposit holidays: When you want to grab an amazing deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you secure your getaway.
Where should I stay in Bossi?
A getaway to Bossi wouldn't be complete without stopping by San Felice Winery. Why not choose a hotel close to this great attraction?
What are the top hotels in Bossi?
Get your holiday off to a great start by booking a room at Hotel Borgo San Felice. It's one of most sought-after properties in Bossi. Another welcoming option is Dievole Wine Resort.
How far in advance should I book my Bossi holiday?
Savvy travellers book early. Airlines generally advertise flight tickets up to a year ahead of departure, and this is a great opportunity to land some of the cheapest prices. Boss just told you to take your holiday time in a few weeks? Don't fret. Expedia are never short of fantastic bargains to help you have the getaway of your dreams, at an affordable price.
What does an Expedia Bossi travel package include?
Hotels, flights and a cool set of wheels for all your fun road trip adventures. Simply pick and choose your preferred bundle and get access to incredible deals. Once you've made your booking, add on a couple of experiences and tours and watch your savings stack up. When it comes to organising your Bossi getaway, you're the boss!
What should I know before booking a Bossi travel package?
A travel package can be more affordable than individually booking all you need for your getaway. For example, bundle your hotels, flights and rental cars and land a great deal. Whatever kind of holiday you're planning, there's sure to be a package that best suits your budget.
Can I choose my airline with a Bossi Expedia travel package?
With a travel package, the choice is in your hands. Whether you want to fly to Bossi in business or coach, simply pick from the available airline options. Expedia has access to over 550 airline partners across the world.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
