Montisi Vacations from $1,378

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Your Montisi Vacation

Let our vacation packages to Montisi inspire your next escape. There's lots to love about this exciting city, starting with the neighborhood of Pozzo, which is good for views and nature. Every trip to Montisi needs a well-crafted itinerary. Fill yours with big-name attractions like Monte Oliveto Maggiore Abbey, Museo del Tartufo and Bosco della Ragnaia. Don't delay your visit to this city any longer. Your dream Montisi vacation is a few clicks away with Expedia.

The Latest Montisi vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $2,090, price is now $1,378 per person
$1,378
per person
Jun 3 - Jun 9
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Super clean room, modern, good shower and bed, nice and quiet, 10 minutes from the train station, breakfast was done in time slots and was ok maybe could have had more selection, staff were friendly, my only bugbear was the WiFi was really slow and i ended up using my hot-spot instead

Reviewed on Apr 12, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,644, price is now $1,587 per person
$1,587
per person
May 22 - May 27
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
The room was clean and newly renovated. Having breakfast included was great for a quick bite so I could focus on exploring instead of searching and waiting in line. Would definitely recommend a stay here

Reviewed on Apr 9, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $4,770, price is now $3,027 per person
$3,027
per person
May 24 - May 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (124 reviews)
Most gorgeous setting, lovely staff and delicious food. We will definitely be back!

Reviewed on Apr 5, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $2,228, price is now $1,636 per person
$1,636
per person
May 22 - May 27
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (483 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was $3,024, price is now $2,247 per person
$2,247
per person
Jun 23 - Jun 29
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (62 reviews)
I particularly love the authenticity of the building being hundreds of hundreds of years old and yet well cut, beautiful staff beautiful spa only lacking in the dining aspect but everything else was perfect. Highly recommend but recommend going out for dinner.

Reviewed on Nov 5, 2025

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Discover the most popular places to visit in Montisi

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

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

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

What to do in Montisi

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
Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting

Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting

$81
per adult
Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting
See all activities in Montisi

Montisi Hotel Deals

Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34 Siena SI
$190 nightly
The price is $215 total per night from Apr 18 to Apr 19
$215 total
Apr 18 - Apr 19
Total with taxes and fees
9.4/10 Exceptional! (776 reviews)
Excellent location. Less than 15 minute walk to major attractions. Numerous restaurants close by.

Reviewed on Apr 9, 2026

Palazzo Ravizza
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $285 total per night from Apr 13 to Apr 14
$285 total
Apr 13 - Apr 14
Total with taxes and fees
9.8/10 Exceptional! (284 reviews)
Absolutely breathtaking property. The staff was extremely welcoming and helpful. Truly such a beautiful experience. Highly recommend to anyone

Reviewed on Mar 21, 2026

Relais Villa Grazianella - UNA Esperienze
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$305 nightly
The price is $345 total per night from Apr 19 to Apr 20
$345 total
Apr 19 - Apr 20
Total with taxes and fees
10/10 Exceptional! (262 reviews)
I did not drive to or from the hotel.

Reviewed on Apr 8, 2026

Monastero di Cortona Hotel & Spa
See all 4,898 properties in Montisi
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.

Find the Best Montisi Vacation Packages

Montisi Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
300
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Tenuta Greppo Franco Biondi Santi, Capanna of Cencioni and Civic and Diocesan Museum of Sacred Art of Montalcino

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Frequently asked questions

How much does a Montisi vacation package cost?
Offering great value package deals from $1,378 on Expedia, you'll be pleasantly surprised at how much a vacation to Montisi costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Montisi?
If you're looking to book a cheap Montisi vacation package, consider visiting in September, October and December. You'll usually find lower prices on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Montisi?
Typically, a handful of days is enough to explore the major attractions during your Montisi vacation. However, if you prefer to have more time to unwind or take day trips, consider extending your itinerary.
How to find the best Montisi package deals?
Use Expedia's filters to find some tempting Montisi package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Montisi package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Montisi vacation as a package?
You can enjoy significant savings on your Montisi break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Montisi?
Secure incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Montisi getaway.
How to plan a trip to Montisi?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred time of year and the activities available will also help you decide when to escape to Montisi.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and meals to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Montisi.
  3. Use Expedia's trip planning tool to discover Montisi: Research every part of your trip to Montisi with this handy planner. Invite friends or family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Set the duration of your trip: Start by compiling a list of the attractions and activities you'd like to get to in Montisi. Then, estimate how long you'll need for each, as well as any travel time.
  5. Combine your airfare and accommodations: After you've settled on your dates and duration, lock in the ideal Montisi vacation package for you.
  6. Book any activities or excursions: Here's the fun part — organizing everything you want to do and see. Check out some of the exciting things to do in Montisi and reserve your tickets in advance to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Montisi vacation packages?
Your Montisi trip is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to give 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 total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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.