Montalcino Holidays from £418
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Your Montalcino Holiday
Say goodbye to the hassle of planning and hello to a Montalcino holiday package. With your travel details organised before you take off, you can focus on discovering the best of this city, starting with Montegiovi, which is great for views, walking and nature. Abbazia di SantAntimo, Tenuta Greppo Franco Biondi Santi and Fortress of Montalcino are just some of the sights worth checking out during your trip to Montalcino. Don't delay visiting this city any longer. The ultimate Montalcino holiday is a couple of clicks away with Expedia.
Top Montalcino Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Donati Luxury Tower Suites
Historic Centre of Florence
£930
per person
13 Dec - 19 Dec
found 13 hours ago
Return flight included
London (LGW) to Florence (FLR)
9.8/10 Exceptional! (77 reviews)
Excellent lodging option very close to the Duomo and central to Florence. It is a terrific location in that it is close to everything but secluded off a very small road that only gets traffic for people checking in or leaving the property. The lodging is in a very old tower that has been converted to about 10 rooms. The front desk is excellent and surprised us when we checked in by telling us they would deliver an assortment of pastries to our room every day for breakfast. We had the Gemma suite which was not large but well laid out with a very comfortable bed and furniture and a very nice bathroom.
Reviewed on 4 Oct 2026
Hotel Regency
Historic Centre of Florence
£618
per person
13 Dec - 19 Dec
found 13 hours ago
Return flight included
London (LGW) to Florence (FLR)
9.4/10 Exceptional! (462 reviews)
Regency Hotel was a 10/10 from the moment our driver dropped us off out front, to the time we were picked up to leave. Check in was flawless. Our room was amazing. We had drinks and snacks in the back terrace and they were amazing. Breakfast in the morning was delightful. I can’t say more about the staff, there were so attentive and friendly. We will definitely be back to spend more time in Florence and stay at the Regency Hotel!
Reviewed on 7 Oct 2026
Montalcino Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Population | 2,100 |
Max Temp Winter | 10ºC |
Max Temp Summer | 29ºC |
Top Sights | Pienza Cathedral, Castello Banfi and Tenuta Greppo Franco Biondi Santi |
Top hotels in Montalcino
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
£1,431
10 Oct - 11 Oct
includes taxes & fees
10/10 Exceptional! (84 reviews)
"Nice and quiet excellent hospitality"
Reviewed on 6 Oct 2026
Corte Francigena - Apartments
Via Ferretti Montalcino SI
Fully refundableReserve now, pay when you stay
£92
8 Nov - 9 Nov
includes taxes & fees
9.8/10 Exceptional! (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Reviewed on 24 Sept 2026
Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
£457
8 Nov - 9 Nov
includes taxes & fees
9/10 Wonderful! (377 reviews)
"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."
Reviewed on 27 Sept 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.
Stay near popular Montalcino attractions
Castello Banfi
9.4/10 (51 reviews)
This medieval estate blends Tuscan tradition with world-renowned winemaking excellence. Sample award-winning Brunello di Montalcino while overlooking rolling vineyards from the restored 18th-century village.
Fortress of Montalcino
9.2/10 (54 reviews)
This pentagonal medieval stronghold was the final bastion of Siena's resistance against Medici conquest. Climb its historic ramparts for panoramic Tuscan views before sampling Brunello wines at the fortress enoteca.
Tenuta Greppo Franco Biondi Santi
8.6/10 (8 reviews)
Birthplace of Italy's prestigious Brunello di Montalcino wine, Tenuta Greppo has defined excellence since 1888. Tour the historic cellars and vineyards where the Biondi-Santi family's winemaking traditions thrive.
Abbazia di Sant'Antimo
9.6/10 (111 reviews)
This medieval Romanesque abbey offers a serene glimpse into monastic life amid Tuscan olive groves. Explore the intricate stone carvings and listen for occasional Gregorian chants echoing through its ancient walls.
Castiglion del Bosco Winery
9.6/10 (5 reviews)
This historic estate, a founding consortium member, produces Italy's finest Brunello di Montalcino wines. Tour the vineyard and cellars before savouring wine pairings with local cheeses amid the Tuscan countryside.
Poggio Antico
9.6/10 (7 reviews)
Perched at one of Montalcino's highest elevations, Poggio Antico produces exceptional Brunello wines in a stunning Tuscan setting. Tour the vineyards and cellar, then sample their distinguished vintages.
Museum of Brunello
9.4/10 (12 reviews)
Explore Brunello di Montalcino's history through artefacts, photographs, and films at this immersive museum. The guided tour ends at the Brunello Labyrinth, featuring over 200 bottles from local wineries.
Civic and Diocesan Museum of Sacred Art of Montalcino
9.4/10 (6 reviews)
This intimate museum houses medieval treasures from Sienese masters like Simone Martini in a 13th-century convent. Admire gold-ground paintings and wooden sculptures that showcase Tuscany's sacred art heritage.
What to do in Montalcino
Montalcino: Guided Winery Tour and Wine Tasting
£39
per adult
Montepulciano: Winery Tour and Tasting
£30
per adult
100% of travellers recommend
Frequently asked questions
Why should I book my Montalcino holiday with Expedia?
Expedia has your back for every aspect of your Montalcino holiday. You'll always get the best deal possible, but when you bundle your flights, accommodation and/or car hire into a holiday package, you'll score even more savings. Looking to truly make the most of your stay? Add a few exciting tours and activities to your customised package. Expedia offers flexible cancellation policies on most bookings, so there's no need to worry if your plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Montalcino?
To enjoy the energy of peak season, take off in February, April and May. September, October and December are generally quieter and a good idea if you want to get away from the crowds. Organise your escape to Montalcino according to 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 averages of 22ºC during the day.
What are the top hotels for my holiday in Montalcino?
Many travellers choose to stay at Le Ragnaie in Tavernelle. If this is your first time in Montalcino, you'll get a warm welcome here.
How do I get a cheap holiday to Montalcino?
Search for flights that suit your schedule, add a hotel room to your booking and see how much you save with a Montalcino holiday. It's that easy! From flights and hotels to tours and hire cars, Expedia makes travelling on a budget easy. And with more than 400 partner airlines and 321,000 hotels globally to select from, you won't 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 Montalcino holiday?
With top attractions such as Abbazia di SantAntimo and Castello Banfi, a holiday in Montalcino is packed with exciting places to visit. Tenuta Greppo Franco Biondi Santi and Fortress of Montalcino are two other sights worth discovering.
What is the best area to stay in when on holiday in Montalcino?
There's so much to explore in Montalcino, so stay close to its top attractions and spend more time sightseeing. Abbazia di SantAntimo is one place to put on your itinerary.
Do I need a visa for my Montalcino holiday?
Research the latest information on official government websites. Your nationality and whether you're visiting for work or pleasure will determine if you'll need a visa for Montalcino. Make yourself familiar with the application process, including any required documentation, fees and turnaround times. Start your application well in advance to allow sufficient time for processing. Some visas may take several weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Montalcino holiday?
Do a little research into the types of clothing people in Montalcino wear, and maybe even look up style blogs for some fashion inspiration. Whatever your look, try to create a versatile wardrobe with pieces that work for your destination and showcase your unique sense of style. Take a look at the weather forecast so you can pack your bags accordingly. The warmest time of year in Montalcino is July, with average daytime temperatures of 22ºC. If you plan to visit in the coolest month of January, the mercury averages 4ºC during the day.
What does an Expedia Montalcino holiday include?
Flights, hotels and hire cars — we've got them all. With Expedia, you can create your Montalcino travel package however you want. All you have to do is determine exactly what you need. Once you've made your booking, why not add extras like activities and experiences? The more you bundle, the greater the savings! Expedia features different types of properties, with the most sought after in Montalcino being villas and apartments. With Expedia, you'll always have the freedom and flexibility to tailor your dream escape your way.
Does Expedia offer Book Now, Pay Later Montalcino holidays?
Yes, we do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply pick the payment plan that works for you during checkout and take away the stress of budgeting for your next trip. Be sure to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:
- Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna can help. Paying in easy monthly instalments will make that dream getaway possible.
- No-deposit holidays: When you stumble on an amazing deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to get what you want.
Can I choose my airline with a Montalcino Expedia holiday?
Yes, you're in charge. Expedia has access to more than 400 airlines across the globe, so you can customise your Montalcino adventure according to your style and budget.
Explore a world of travel with Expedia
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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.
