Montalcino Holidays

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Top Flight + Hotel Deals in Montalcino

Price found within the past 48 hours. Click for updated prices.
LHP Certaldo Resort

LHP Certaldo Resort

5 out of 5
Save 100% on your flight
Price was €1,012, price is now €600 per person
€600
per person
30 Sept - 6 Oct
found 8 hours ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (532 reviews)
nice property

Reviewed on 30 Jun 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was €1,872, price is now €983 per person
€983
per person
30 Sept - 6 Oct
found 8 hours ago
Return direct flight included
Knock (NOC) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Good service and the room was clean

Reviewed on 10 Jul 2026

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Save 100% on your flight
Price was €1,385, price is now €803 per person
€803
per person
30 Sept - 6 Oct
found 8 hours ago
Return flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (415 reviews)
Wonderful property, amazing hosts. 20 minutes outside of Florence center-easy to get a taxi. My family loved everything about our stay here!

Reviewed on 7 Jul 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was €2,389, price is now €1,435 per person
€1,435
per person
10 Aug - 15 Aug
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
Price was €4,030, price is now €2,465 per person
€2,465
per person
30 Sept - 6 Oct
found 8 hours ago
Return flight included
Dublin (DUB) to Florence (FLR)
10/10 Exceptional! (290 reviews)
This is an excellent hotel, great staff, great location and great food. The breakfast is a really nice experience and the courtyard swimming pool is so peaceful.

Reviewed on 29 Jun 2026

Top hotels in Montalcino

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
The price is €703 per night from 11 Aug to 12 Aug
€703
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (359 reviews)
"Is ok"

Reviewed on 30 Jun 2026

Castello di Velona Resort Thermal SPA & Winery
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is €2,242 per night from 28 Jul to 29 Jul
€2,242
28 Jul - 29 Jul
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
Corte Francigena - Apartments

Corte Francigena - Apartments

Via Ferretti Montalcino SI
Fully refundableReserve now, pay when you stay
The price is €194 per night from 21 Jul to 22 Jul
€194
21 Jul - 22 Jul
includes taxes & fees
9.8/10 Exceptional! (7 reviews)
"The property, views and amenities were absolutely incredible! The apartment was beautiful decorated, it was new and very clean. We loved every moment and wished we could have stayed longer, we will definitely be back!"

Reviewed on 30 Jun 2026

Corte Francigena - Apartments
See all 7,205 properties in Montalcino
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.
See properties

What to do in Montalcino

Montepulciano Gran Tour

Montepulciano Gran Tour

€15
per adult
Montepulciano Gran Tour
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

€94
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montalcino, Pienza & Montepulciano Wine & Food Tour

Val d’Orcia Wine Tour with Lunch & Brunello

€119
per adult
84% of travellers recommend
Val d’Orcia Wine Tour with Lunch & Brunello
See all activities in Montalcino

Frequently asked questions

How much does a Montalcino holiday package cost?
Offering great value package deals from €600 on Expedia, you'll be thrilled with how little a holiday to Montalcino costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Montalcino?
December, January and February are the best times to look for cheap Montalcino holiday packages. Travelling in less busy months means you can generally find lower prices on flights and accommodation.
How many days is enough for Montalcino?
For a Montalcino holiday, a few days will be enough to explore the highlights. Make sure to stop by Capanna of Cencioni — it's one of the main sights in this destination. If you're looking for more activities, think about basing yourself here and heading off on some trips from Montalcino.
Is it worth booking a holiday package to Montalcino?
Well known for its views, nature and bars and pubs, a Montalcino holiday is a hit with all kinds of travellers. Be sure to visit major sights like Fortress of Montalcino and Civic and Diocesan Museum of Sacred Art of Montalcino, and consider renting a car for day trips to explore even more.
How to find the best Montalcino package deals?
Bagging a cheap Montalcino package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can customise your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Montalcino package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Montalcino holiday as a package?
You can enjoy significant savings on your next Montalcino getaway by booking a tailored holiday package. Check the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Montalcino?
If you have your Montalcino holiday dates finalized, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Montalcino?

  1. Pick your travel dates: The things you plan to do in Montalcino and your favourite season can help you decide when to go.
  2. Budget wisely: Besides the cost of your accommodation, you should consider other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Montalcino.
  3. Decide how long to go for: Now that you know more about Montalcino, you can figure out the perfect length of your holiday. Create a rough plan and give yourself enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Montalcino holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.