Montepulciano Vacation Packages

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Your Montepulciano Vacation

Get to know the hilltop city of Montepulciano with a Montepulciano vacation package and immerse yourself in the best it can offer. From its rich history and cultural experiences to its spectacular views, prepare to fall for the charms of this vibrant destination. A trip to Montepulciano is a superb opportunity to do some sightseeing. Make sure you visit big-name attractions such as Pienza Cathedral, Palazzo Piccolomini and Tenuta Valdipiatta. Whoever you're heading away with and whatever your bank balance, your ultimate Montepulciano vacation is only clicks away with Expedia.

Top Montepulciano Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Hoxton, Florence

The Hoxton, Florence

4 out of 5
Historic Centre of Florence
Price was CA $1,754, price is now CA $1,265 per person
CA $1,265
per person
Feb 6 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (370 reviews)
Great location, helpful staff. Excellent restaurant, bar and coffeehouse located in the hotel. Highly recommend!

Reviewed on Nov 13, 2026

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Price was CA $2,525, price is now CA $1,801 per person
CA $1,801
per person
Dec 15 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (357 reviews)

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was CA $3,106, price is now CA $2,454 per person
CA $2,454
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (612 reviews)

Il Rivalta - Place of Charme

Il Rivalta - Place of Charme

4 out of 5
Historic Centre of Florence
Price was CA $3,096, price is now CA $2,510 per person
CA $2,510
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (642 reviews)
Great staff and property!! Location is primeeeee to walk all around Florence

Reviewed on Nov 8, 2026

Hotel Santa Maria Novella

Hotel Santa Maria Novella

4 out of 5
Historic Centre of Florence
Price was CA $3,186, price is now CA $2,611 per person
CA $2,611
per person
Dec 24 - Dec 29
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (1,002 reviews)
You can walk to just about every major tourist destinations in 10 to 20 minutes. The hotel is well maintained and housekeeping staff keep your room nice and clean. Amenities include standard items such as body soap, shampoo/conditioner but also body cream, shower cap, slippers, bathrobes, etc. They provide a coffee/espresso machine and a kettle. It was nice to see some “decaf “ options. You might consider bringing your own universal plug for the EU style outlets to charge electronics. Breakfast is excellent; lots of options.

Reviewed on Nov 14, 2026

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Montepulciano Hotel Deals

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Di Poggio Alla Sala, 10 Montepulciano SI
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Precise Tale Poggio Alla Sala
Nuovo Etruria Resort

Nuovo Etruria Resort

4 out of 5
Via di S. Martino snc Montepulciano SI
The price is CA $137 per night from Nov 27 to Nov 28
CA $137
CA $159 total
Nov 27 - Nov 28
includes taxes & fees
Nuovo Etruria Resort
Hotel Panoramic Montepulciano

Hotel Panoramic Montepulciano

3 out of 5
Via di Villa Bianca, 8 Montepulciano SI
8.8/10 Excellent! (265 reviews)
"Ok."

Reviewed on Oct 9, 2026

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Hotel Panoramic Montepulciano
See all 6,368 properties in Montepulciano
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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Stay near popular Montepulciano attractions

Piazza Grande

9.4/10 (125 reviews)
You can find out about the history of Montepulciano with a visit to Piazza Grande. While you're here, you can savor the wineries.
See properties

What to do in Montepulciano

Tasting Tour in One of The Most Beautiful Cellars in the World

Tasting Tour in One of The Most Beautiful Cellars in the World

CA $52
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

CA $189
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

CA $55
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
See all activities in Montepulciano

Frequently asked questions

How much does a Montepulciano vacation package cost?
You'll find cheap prices from CA $1,265 on Expedia for your Montepulciano getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Montepulciano costs.
What are the cheapest months to go to Montepulciano?
You can generally find lower rates and better availability in December, January and February. Browse our cheap Montepulciano vacation packages and you could get some excellent off-season deals.
How many days is enough for Montepulciano?
Usually, a handful of days is enough to check out the top sights during your Montepulciano vacation. However, if you want to have some time to unwind or take day tours, consider extending your itinerary.
Is it worth booking a vacation package to Montepulciano?
Montepulciano has all the ingredients you need for an amazing trip — walking trails, culture and dining are just the start. Whether you want to check out sights like Piazza Grande and Palazzo Avignonesi, or venture off the beaten track, you'll find plenty to do on your Montepulciano vacation.
How to find the best Montepulciano package deals?
Use Expedia's filters to find some of the best Montepulciano package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Montepulciano package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Montepulciano vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations separately. Better still, you can customize your Montepulciano trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Montepulciano?
If you're planning an impromptu Montepulciano trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Montepulciano?

  1. Choose when to get away: Check your schedule and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to vacation in Montepulciano.
  2. Figure out your budget: Make sure you have enough money to cover everything from food and transportation to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Montepulciano.
  3. Decide how many days away: Start by making a list of all the activities and attractions you'd like to get to in Montepulciano. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Montepulciano vacation package that brings all your bookings together.

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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.