Province of Siena Holidays
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Your Province of Siena Holiday
When your wanderlust is calling, answer it with a holiday package to Province of Siena. If you're considering a stop in Siena, get set to experience this city's walking trails, nature, views and more. A trip to Province of Siena wouldn't be complete without experiencing some of its most well-known cities, starting with Siena. Some of the most popular attractions here include Monteriggioni Castle and Palazzo Pubblico. Montepulciano is another favourite with Province of Siena travellers. Visitors to this city enjoy Val di Chiana and Piazza Grande. When you're ready to stop dreaming and start doing, Expedia will help turn your Province of Siena holiday into reality.
Top destinations in Province of Siena
Siena
San Gimignano
Montepulciano
Pienza
Montalcino
Castellina in Chianti
Radda in Chianti
Sarteano
Top Province of Siena Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa
Historic Centre of Florence
£629
per person
23 Nov - 29 Nov
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
The spa was really nice to have access to after a lot of walking in Florence.
Reviewed on 20 Sept 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
£552
per person
23 Nov - 29 Nov
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
I would say this is a 3.5 star property. The room was clean but basic, same for the bathroom and amenities like soap etc. the location is very central but the room was still quiet. There is no concierge and the staff was not able to make any reservations for us.
Reviewed on 19 Sept 2026
Villa Tolomei Hotel & Resort
Oltrarno
£532
per person
23 Nov - 29 Nov
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
8.8/10 Excellent! (431 reviews)
Stay was excellent. Breakfast and one dinner at the Villa were very good. Only minor issue was the extender for the WiFi was not working, which limited the WiFi to only the living room and kitchen area. Still workable.
Reviewed on 12 Sept 2026
Province of Siena Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Closest Airport | Fiumicino - Leonardo da Vinci Intl. Airport (FCO) |
Population | 42,900 |
Top Sights | Monte Amiata, Piscine Termali Theia and Terme di Montepulciano Spa |
Top hotels in Province of Siena
La Certosa di Pontignano
loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
£82
19 Oct - 20 Oct
includes taxes & fees
9.4/10 Exceptional! (564 reviews)
"Magical place! We loved jazz night and the amazing wine paired dinner. Fantastic place!"
Reviewed on 16 Sept 2026
Hotel Executive
Via Nazareno Orlandi 32 Siena SI
£69
12 Oct - 13 Oct
includes taxes & fees
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
£199
20 Oct - 21 Oct
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.
Frequently asked questions
Why should I book my Province of Siena holiday with Expedia?
Choose Expedia to plan your next big break with ease, all in one convenient place. Our top tip for bagging a fabulous deal on a Province of Siena retreat? Bundle your hotel, flights and/or car hire into a package holiday. Then throw in a few awesome tours and activities. Many bookings also have flexible cancellation policies, so there's no need to stress if you have to switch up your travel itinerary. Round-the-clock help with making tweaks to your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Province of Siena?
If you enjoy the buzz of peak season, visit Province of Siena in April, May and June. If you want a more relaxed vibe, November, December and January will suit you better. Plan your trip to Province of Siena based on what type of adventure you want. January is the coolest month, when average daytime temperatures are 4ºC. In July, the warmest month, you'll experience temperatures of around 23ºC during the day.
What are the top hotels for my holiday in Province of Siena?
Check out Hotel Athena and NH Siena. They're the first choice for many travellers headed to Crete Senesi. If San Gimignano features in your travel itinerary, Sangallo Park Hotel and Castello di Fonterutoli Wine Resort are two welcoming options.
How do I get a cheap holiday to Province of Siena?
Find flights that suit your schedule, add a hotel to your booking and watch the savings rack up with a Province of Siena holiday. It's as easy as that! From flights and hotels to hire cars and tours, Expedia is where your cheap holiday begins. And with over 400 air carriers and 321,000 hotels globally to select from, you'll never be short of choice. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Province of Siena holiday?
Organise your holiday in Province of Siena around leading attractions like Siena Cathedral and Torre del Mangia. Many travellers also highly recommend Piazza del Campo and Pienza Cathedral.
What are the best cities to stay in when on holiday in Province of Siena?
To see well-known attractions like Pienza Cathedral and Palazzo Piccolomini, Val dOrcia is the place to be. Plenty of travellers also rave about Pienza, home to Pienza Cathedral and Palazzo Piccolomini. If time isn't an issue, why not check out both cities?
Do I need a visa for my Province of Siena holiday?
Official government websites are the best source of information on visa requirements, application procedures and necessary documentation. Your nationality and the reason for your visit, whether it be for tourism or business, will determine if you need a visa for Province of Siena. Also ensure your passport is up to date and has at least six months validity remaining beyond your planned date of return. Do all your travel planning ahead of time to avoid any last-minute surprises.
What should I wear on my Province of Siena holiday?
Consider the sorts of activities you have planned during your Province of Siena trip and choose versatile pieces that can be mixed and matched. For fashion inspiration or information on any dress codes, browse style blogs or relevant social media accounts. In Province of Siena, daytime average temperatures reach 23ºC during July, making it the warmest month. January marks the coolest time of year here, with the mercury hovering around 4ºC in the day. Plan your trip with confidence by monitoring the forecast for all the stops on your itinerary.
What does an Expedia Province of Siena holiday include?
With Expedia, you can choose a combination of car hires, flights and hotels to create your ideal Province of Siena package. Once you've made your booking, simply add on all the fun stuff like activities and tours. Don't forget, the more you bundle, the greater the savings! Explore a variety of styles on Expedia and find the perfect one for you and your travel companions. From the most popular property types, like apartments and villas, to everything in between, you'll find plenty of holiday rentals in Province of Siena to select from so you can tailor your stay to suit your taste.
Does Expedia offer Book Now, Pay Later Province of Siena holidays?
We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply click on the payment plan that suits best during the checkout process and take the stress out of budgeting for your next trip. Remember to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:
- Pay monthly holidays: Klarna offers payments in multiple transactions that work for all types of budgets, so you can jet away on that well-deserved holiday sooner.
- No-deposit holidays: Clicking the "book now" button is easier with this plan. With no deposit required for your escape, you can Book Now, Pay Later and start packing your suitcase.
Can I choose my airline with a Province of Siena Expedia holiday?
You certainly can. We have more than 400 partner airlines globally, so pick the carrier that fits your budget and travelling style.
Stay near popular Province of Siena attractions
Piazza del Campo
9.6/10 (1,995 reviews)
Learn about the local history of Siena when you spend time at Piazza del Campo. Discover the area's beautiful countryside or seek out its local tours.
Monte Amiata
9.0/10 (100 reviews)
Explore the great outdoors at Monte Amiata, a lovely green space in Abbadia San Salvatore. Discover the area's countryside and wineries.
Siena Cathedral
9.6/10 (1,693 reviews)
Siena Cathedral is just one of the places to see in Siena, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside while you're in the area.
Pienza Cathedral
9.4/10 (460 reviews)
Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II.
Piazza Grande
9.4/10 (125 reviews)
You can find out about the history of Montepulciano with a trip to Piazza Grande. While you're here, you can savour the wineries.
Tenuta Torciano Winery
9.2/10 (40 reviews)
You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.
Castello Banfi
9.4/10 (51 reviews)
You can enjoy a tasting or tour at Castello Banfi during your travels to Poggio alle Mura. Visit the area's spas or simply enjoy its wineries.
Terme Antica Querciolaia
8.6/10 (8 reviews)
You can take time to visit Terme Antica Querciolaia during your travels to Rapolano Terme. Discover the countryside and wineries in this romantic area.
What to do in Province of Siena
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
£42
per adult
78% of travellers recommend
Chianti Half Day Wine Tour from Florence
£19
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
£61
per adult
88% of travellers recommend
Explore a world of travel with Expedia
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- Lando House
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- Palazzo Chigi Zondadari
- Palazzo DEL PAPA
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- Podere Il Pero
- Siena Hostel Guidoriccio
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- Villa degli olivi
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- Abbazia di San Galgano
- Alta Val d'Elsa River Park
- Asciano Holidays
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- Castellina in Chianti Holidays
- Church of San Sigismondo
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- Fontebranda
- Gaiole in Chianti Stadium
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- Lsola d'Arbia Holidays
- Meleto Castle
- Monsanto Holidays
- Monteriggioni Holidays
- Monticiano Holidays
- Museo dell'Opera del Duomo
- Palazzo Pubblico
- Piazza del Campo
- Piccolomini Library
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- Visit Province of Siena
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- Santa Maria alle Scotte Polyclinic
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- Visit Siena
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- Teatro dei Rinnovati
- Villa a Sesta Polo Club
* 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.
