A historic town with a prominent tower and a rainbow arching over it.

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 cathedral with a rainbow, surrounded by traditional buildings.

    Siena

    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

    A historic square with stone buildings, a prominent tower, and outdoor seating areas.

    San Gimignano

    A historic town with terracotta-roofed buildings, a prominent church, and rolling hills in the background.

    Montepulciano

    A historic castle on a hill with surrounding greenery and buildings.

    Montalcino

    A historic town perched on a hillside with a prominent church tower, surrounded by lush greenery and rolling hills in the background.

    Pienza

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

    Castellina in Chianti

    A vineyard with rows of grapevines, a road, and a hill with trees in the background.

    Castelnuovo Berardenga

    A grassy hill with a row of tall trees and a fence.

    San Quirico d'Orcia

    The Latest Province of Siena Holiday Packages

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    Discover the most popular places to visit in Province of Siena

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

    Piazza del Campo

    Rating: 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

    Rating: 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 church with a bell tower, arched windows, and a central dome.

    Pienza Cathedral

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

    Monte Amiata

    Rating: 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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    Tenuta Torciano Winery

    Rating: 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

    Rating: 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

    Rating: 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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    Tenuta Greppo Franco Biondi Santi

    Rating: 8.6/10 (8 reviews)

    You can enjoy a tasting or tour at Tenuta Greppo Franco Biondi Santi during your travels to Montalcino. Discover the area's countryside and spas.

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    What to do in Province of Siena

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

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

    £16

    per adult

    0% of travellers recommend

    Chianti Wine and Food Safari

    SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence

    £110

    per adult

    100% of travellers recommend

    Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch

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

    £41

    per adult

    78% of travellers recommend

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    Province of Siena Hotel Deals

    La Certosa di Pontignano - Place of Charme

    A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.
    • Address: loc. Pontignano, 5, Castelnuovo Berardenga, SI, 53019, IT
    • Location: 3.8 mi from Province of Siena
    • Guest rating: 9.4/10 (Exceptional, 582 reviews)
    • Price: £61, includes taxes & fees, 14 Dec - 15 Dec
    • Review: Endroit magnifique et bien situé pour visiter la région.

    Villa Sabolini

    A well-maintained garden with a large urn, neatly trimmed hedges, and a building with warm lighting in the background.
    • Address: Loc. Mensanello, Colle di Val d'Elsa, SI, 53034, IT
    • Location: 11.6 mi from Province of Siena
    • Star rating: 4/5
    • Guest rating: 9.2/10 (Wonderful, 241 reviews)
    • Price: £67, includes taxes & fees, 1 Dec - 2 Dec
    • Review: beautiful villa. but too rural setting

    Hotel Chiusarelli

    A lobby with a marble floor, a chandelier, a reception desk, and large green plants.
    • Address: Viale Curtatone 15, Siena, SI, 53100, IT
    • Location: 0.3 mi from Province of Siena
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 1001 reviews)
    • Price: £69, includes taxes & fees, 9 Dec - 10 Dec

    Castello di Leonina Relais

    A table set for dining with a scenic view of rolling hills and distant mountains.
    • Address: Strada Di Leonina 5, Asciano, SI, 53041, IT
    • Location: 6.5 mi from Province of Siena
    • Star rating: 4/5
    • Guest rating: 9.2/10 (Wonderful, 168 reviews)
    • Price: £62, includes taxes & fees, 3 Dec - 4 Dec

    Palazzo Brandano

    A stone building with a courtyard and a canal.
    • Address: Via Valgelata 18, Trequanda, SI, 53020, IT
    • Location: 21.7 mi from Province of Siena
    • Guest rating: 9.4/10 (Exceptional, 109 reviews)
    • Price: £46, includes taxes & fees, 3 Dec - 4 Dec
    • Review: It was magical!

    Hotel Palazzo San niccolò & Spa

    A spa area with a stone ceiling, a pool, and two sun loungers.
    • Address: Via Roma 16, Radda in Chianti, SI, 53017, IT
    • Location: 11.8 mi from Province of Siena
    • Star rating: 4/5
    • Guest rating: 9.2/10 (Wonderful, 198 reviews)
    • Price: £65, includes taxes & fees, 2 Dec - 3 Dec
    • Review: Great stay!

    Hotel Borgo San Luigi

    A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.
    • Address: STRADA DELLA CERRETA,7, Monteriggioni, SI, 53035, IT
    • Location: 9.8 mi from Province of Siena
    • Star rating: 4/5
    • Guest rating: 9.2/10 (Wonderful, 457 reviews)
    • Price: £98, includes taxes & fees, 16 Nov - 17 Nov
    • Review: We really have a good time . We had dinner and breakfast was very good.

    Palazzo Ravizza

    A table with breakfast items and a wicker chair, overlooking a scenic landscape.
    • Address: Pian dei Mantellini 34, Siena, SI, 53100, IT
    • Location: 0.4 mi from Province of Siena
    • Star rating: 4/5
    • Guest rating: 9.4/10 (Exceptional, 904 reviews)
    • Price: £90, includes taxes & fees, 15 Dec - 16 Dec

    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.

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    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.

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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.