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

A historic town with tightly packed buildings, a prominent tower, and a church.

Siena

Siena
A narrow street with stone buildings, Italian flags, and a shop with ceramic plates.

San Gimignano

San Gimignano
A hillside town with historic buildings and a prominent church.

Montepulciano

Montepulciano
A historic square with a prominent tower and statues.

Pienza

Pienza
A panoramic view of a historic town with a prominent castle on a hill, surrounded by residential buildings and a mix of green fields and roads.

Sarteano

Sarteano
A historic tower with arches and a bell, surrounded by traditional buildings with tiled roofs and satellite dishes.

Montalcino

Montalcino
A stone building with a clock tower, steps leading up to it, and people walking around.

Castellina in Chianti

Castellina in Chianti
A narrow street with stone buildings, a 'Zona traffico limitato' sign, and people walking.

Radda in Chianti

Radda in Chianti

Top Province of Siena Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
La Villa di STR

La Villa di STR

Siena Historical Center
Save 100% on your flight
£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 Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
Save 100% on your flight
£717
per person
19 Nov - 28 Nov
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.6/10 Exceptional! (605 reviews)
Very clean room with cold ac . Well thought out bathroom . Nice size room for Europe . And for the ladies the lighting in the bathroom was excellent .

Reviewed on 13 Oct 2026

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Cortona Old Town
Save 100% on your flight
£847
per person
19 Nov - 28 Nov
found 1 day 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

The Hoxton, Florence

The Hoxton, Florence

Historic Centre of Florence
Save 100% on your flight
£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

Hotel Certosa Di Maggiano

Save 100% on your flight
£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

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

Hotel Athena

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

Hotel Athena
Hotel Chiusarelli

Hotel Chiusarelli

Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
£93
8 Nov - 9 Nov
includes taxes & fees
Hotel Chiusarelli
Grand Hotel Continental Siena – Starhotels Collezione

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

Grand Hotel Continental Siena – Starhotels Collezione
See all 6,192 properties in Province of Siena
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

A historic square with cobblestone pavement, surrounded by multi-story buildings with traditional architecture.

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.
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A grand cathedral with intricate Gothic architecture, a prominent bell tower, and a bustling square with people.

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.
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A historic building with a tower, a fountain, and a courtyard.

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.
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A historic church with a bell tower, arched windows, and a central dome.

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.
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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.
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San Giovanni Terme Rapolano

9.2/10 (69 reviews)
You can take time to visit San Giovanni Terme Rapolano during your travels to Rapolano Terme. Discover the countryside and wineries in this romantic area.
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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.
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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.
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What to do in Province of Siena

Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

£16
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch

Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

£42
per adult
78% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

£21
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
See all activities in Province of Siena

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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. Flight-inclusive packages are ATOL protected.