Montalcino Vacations from $1,049

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Your Montalcino Vacation

Say goodbye to the hassle of planning and hello to a Montalcino vacation package. With your travel details organized 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 vacation is a couple of clicks away with Expedia.

The Latest Montalcino vacation packages

Price found within the past 48 hours. Click for updated prices.
Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was $1,455, price is now $1,049 per person
$1,049
per person
Nov 17 - Nov 22
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (51 reviews)
Overall the property was great for our needs. It was very convenient for us because it had parking on the premises. The staff was amazing and the king room was beautiful. The only drawback is that it was a bit of a walk from the city center.

Reviewed on Oct 5, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,956, price is now $1,238 per person
$1,238
per person
Dec 31 - Jan 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (477 reviews)
This is a beautiful hotel.It is spotlessly clean.The staff are friendly and helpful. Breakfast exceeded our expectations. The choice of food and service were excellent. It’s a good location to see the sights and get to the train station to visit Pissa etc. We will definitely book here for our next visit.

Reviewed on Oct 11, 2025

Collegio alla Querce - Auberge Collection

Collegio alla Querce - Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $2,749, price is now $1,762 per person
$1,762
per person
Nov 27 - Nov 30
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (3 reviews)
Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Price was $1,766, price is now $1,268 per person
$1,268
per person
Dec 31 - Jan 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.8/10 Excellent! (393 reviews)
Great place to stay near Florence, it’s quite and relaxing. The pool is great.

Reviewed on Jul 31, 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
Price was $1,517, price is now $1,103 per person
$1,103
per person
Nov 27 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
10/10 Exceptional! (235 reviews)
fabulous hotel with the most beautiful aperol spritz I have ever had served by the pool, and that was only one of the wonderful things I have to say about this beautiful hotel. The staff were helpful and accomodating, breakfast in the courtyard outstanding and our room was divine. Cant recommend this property enough.

Reviewed on Oct 9, 2025

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Discover the most popular places to visit in Montalcino

CastelloBanfi Il Borgo, Luxury Retreat in Montalcino Italy Growing up as a devoted history lover, I have always daydreamed about living in a castle. I used to recreate that magical word in my phantasy, populated with vassals and fortune tellers, with dames and cavaliers. This summer, my stay at the beautiful Tuscan resort CastelloBanfi Il Borgo in Montalcino, Italy gave me the chance to turn this dream into reality. Ambra Castello Banfi 2 This beautiful property is set in an ancient stone hamlet that was built in the 1700 sunder the protective walls of the 13th Century Castle “Castelloalle Mura”. What was once used as a dwelling for farmers who toiled with their noble landowners has today been restyled into the luxurious rooms and suites of this jewel of Tuscan hospitality. Ambra Castello Banfi While the architectural style remained unchanged and very authentic, the interior was renovated with modern comforts, premium fabrics and exclusive accessories. Luxury Retreat in Montalcino Ambra Castello cannon dream of living in a castle We were so lucky to stay in one of their exclusive 14 rooms, surrounded by history, vineyards and olive groves. CastelloBanfiilBorgo is truly a place of peace and serenity.Enjoying breakfast or “aperitivo” at sunset from the infinity pool that over looks immense stretches of Brunello vines is simply good for the soul. Castello well Ambra Castello But wait until you witness the most delectable gastronomic experience at “Taverna”, one of the two epic restaurants on property. That’s the ultimate experience to please all of your senses! Ambra tee at Castello Ambra Castello pool Ambra in a castle In the next post will show you all the delicious Italian food we got to savor at the castle’s restaurant, but for now enjoy some beautiful photos and the video about this incredible resort! CastelloBanfiIlBorgo Ambra in Montalcino Italy

Castello Banfi

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.

Castello Banfi
Poggio Antico winery- Brunello is the best!!

Fortress of Montalcino

Find out about the history of Montalcino with a stop at Fortress of Montalcino. Visit the area's spas, or simply enjoy its wineries.

Fortress of Montalcino

Tenuta Greppo Franco Biondi Santi

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.

Tenuta Greppo Franco Biondi Santi

What to do in Montalcino

Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$52
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

$104
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
See all activities in Montalcino

Montalcino Hotel Deals

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona, Castelnuovo dell'Abate, Montalcino, SI
Fully refundableReserve now, pay when you stay
$434 nightly
The price is $489 total per night from Nov 9 to Nov 10
$489 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (331 reviews)
"Me and my wife stayed there for our honeymoon. We had an exceptional time. The service was exceptional. The pools and amenities were very nice. Great! Breakfast was just free. Located close to montel Chino and many great wineries. Specifically, we really enjoyed the wine tasting. The entire staff ..."

Reviewed on Sep 11, 2025

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

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
$1,291 nightly
The price is $1,432 total per night from Nov 5 to Nov 6
$1,432 total
Nov 5 - Nov 6
Total with taxes and fees
10/10 Exceptional! (67 reviews)
"Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal."

Reviewed on Aug 3, 2025

Rosewood Castiglion del Bosco
Hotel Dei Capitani

Hotel Dei Capitani

3 out of 5
Via Lapini 6, Montalcino, SI
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $139 total per night from Nov 5 to Nov 6
$139 total
Nov 5 - Nov 6
Total with taxes and fees
8.8/10 Excellent! (400 reviews)
"Most beautiful view from hotel room"

Reviewed on Oct 9, 2025

Hotel Dei Capitani
See all 7,203 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.

Montalcino Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
2,100
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Pienza Cathedral, Castello Banfi and Tenuta Greppo Franco Biondi Santi

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Frequently asked questions

How much does a Montalcino vacation package cost?
Offering great value package deals from $1,049 on Expedia, you'll be thrilled with how little a vacation to Montalcino costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Montalcino?
You're likely to find lower rates and better availability in September, October and December. Take a look at our cheap Montalcino vacation packages and you could land some great off-season deals.
How many days is enough for Montalcino?
Typically, a few days is enough for a Montalcino vacation. With a carefully crafted itinerary, you can see all the popular sights such as Capanna of Cencioni, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Montalcino?
Whether you want to explore major attractions such as Fortress of Montalcino and Civic and Diocesan Museum of Sacred Art of Montalcino on your Montalcino vacation, or coming for its excellent walking trails, views and history, there's something for everyone here. With so many things to do, you'll soon discover why so many visitors think Montalcino is a good vacation destination.
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 customize your search by "Amenities," "Property type," "Traveler 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 vacation as a package?
You can enjoy significant savings on your next Montalcino getaway by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Montalcino?
If you have your Montalcino vacation 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. Choose your dates: What you'd like to do in Montalcino and your favorite season can help you decide when to travel.
  2. Set your budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Montalcino. Then, choose a property that works with your budget, whether that's a low-cost option or a more upscale getaway.
  3. Organize your Montalcino escape with our trip planning tool: Search for and book hotels and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Montalcino together.
  4. Decide your trip length: Consider how much time you'd like to spend discovering Montalcino. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Montalcino vacation package that brings all your bookings together.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Montalcino. Find all the exciting things to do in Montalcino with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Montalcino vacation packages?
Your Montalcino trip is meant to be a relaxing escape from your busy life, not a reason for money worries. So to allow you a bit more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.