Montecastelli Vacation Packages

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Top Montecastelli Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

4 out of 5
Price was CA $2,068, price is now CA $1,295 per person
CA $1,295
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (187 reviews)
This was a little slice of heaven and such a hidden gem. This place is by far my favorite that I have been to in Europe

Reviewed on Jun 16, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,263, price is now CA $1,350 per person
CA $1,350
per person
Sep 28 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
It was not entirely clean, the staff don't do much. Breakfast is from the day before. Air conditioning excellent.

Reviewed on Jul 3, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $6,677, price is now CA $4,234 per person
CA $4,234
per person
Sep 20 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)

Reviewed on Jun 19, 2026

The Poet Hotel

The Poet Hotel

4 out of 5
La Spezia Historic Centre
Price was CA $2,470, price is now CA $1,719 per person
CA $1,719
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pisa (PSA)
9.2/10 Wonderful! (1,006 reviews)
N/a

Reviewed on Jul 1, 2026

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Price was CA $1,983, price is now CA $1,393 per person
CA $1,393
per person
Aug 18 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.4/10 Very good! (53 reviews)
Staff was helpful, the property was not very well maintained.

Reviewed on Jun 1, 2026

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Montecastelli Hotel Deals

Hotel Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from Aug 4 to Aug 5
CA $142
CA $165 total
Aug 4 - Aug 5
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Hotel Italia was an absolute gem. The staff were incredibly friendly and helpful — they understood we were tired from traveling with teens and even nailed a salon recommendation that turned out to be the best hair wash of my life, just minutes from the hotel. Our room was spotless, quiet, and the ..."

Reviewed on Jun 27, 2026

Hotel Italia
Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from Jul 8 to Jul 9
CA $93
CA $112 total
Jul 8 - Jul 9
includes taxes & fees
8.2/10 Very good! (349 reviews)
"Room was clean, staff was helpful and easy to park."

Reviewed on Jun 27, 2026

Hotel Toscana Ambassador
Mormoraia

Mormoraia

Agriturismo San Gimignano San Gimignano SI
The price is CA $524 per night from Jul 20 to Jul 21
CA $524
CA $585 total
Jul 20 - Jul 21
includes taxes & fees
9.6/10 Exceptional! (219 reviews)
"An absolutely wonderful experience staying at Mormoraia, from the reception meeting us at our car to the private wine tour- our trip to Tuscany was elevated staying here. I’m looking forward to coming back again and coming a full week."

Reviewed on Jul 2, 2026

Mormoraia
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Frequently asked questions

How much does a Montecastelli vacation package cost?
Offering great value package deals from CA $1,295 on Expedia, you'll be thrilled with how little a vacation to Montecastelli costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Montecastelli?
If you're hoping to score a cheap Montecastelli vacation package, consider planning a trip in January, February and November. You'll generally find better rates on accommodations and flights during these months — ideal for a budget-friendly break.
How many days is enough for Montecastelli?
The ideal length for your Montecastelli vacation depends on what you'd like to see and do. Usually, a few days to a week will give you plenty of time to visit all the leading sights and explore some hidden gems along the way.
How to find the best Montecastelli package deals?
Start your search for a Montecastelli package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Montecastelli package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Montecastelli escape underway.
Is it cheaper to book a Montecastelli vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component individually. And you'll still get the flexibility to create a customized Montecastelli vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Montecastelli?
If you're considering a spontaneous Montecastelli adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Montecastelli?

  1. Choose your dates: What you plan to do in Montecastelli and your favourite season can help you decide when to travel.
  2. Set a budget: Consider costs such as flights, meals and transportation when calculating how much to save for your trip to Montecastelli. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a swankier getaway.
  3. Decide your trip length: Consider how long you want to spend discovering Montecastelli. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Montecastelli vacation package.

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.