Montecastelli Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Montecastelli
Price found within the past 48 hours. Click for updated prices.
Aurum Firenze
Historic Centre of Florence
€460
per person
27 Nov - 30 Nov
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
This is possibly the worse booking I have made with Expedia. Billed as a 4 star hotel, it really was anything but. A room located right next the lift and kitchen where staff played their radio loud first thing waking you up. A room so small you had to navigate the space to open the door to get into the bathroom. Dont believe the pictures! Breakfast in a 4 star, well that consisted of cold scrambled egg and bacon cooked in a microwave. I will never go back and neither will my wife after watching a cockroach run across the floor whilst using the breakfast area toilet.
Reviewed on 11 Sept 2026
Villa Tolomei Hotel & Resort
Oltrarno
€522
per person
27 Nov - 30 Nov
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
8.8/10 Excellent! (431 reviews)
Stay was excellent. Breakfast and one dinner at the Villa were very good. Only minor issue was the extender for the WiFi was not working, which limited the WiFi to only the living room and kitchen area. Still workable.
Reviewed on 12 Sept 2026
Top hotels in Montecastelli
Hotel Italia
Viale Camillo Benso Conte di Cavour, 67 Siena SI
Fully refundableReserve now, pay when you stay
€120
11 Oct - 12 Oct
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Clean, well maintained property that you’ll feel safe spending the night."
Reviewed on 12 Sept 2026
Poderi Arcangelo
Localita Capezzano San Gimignano SI
Fully refundableReserve now, pay when you stay
€138
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (367 reviews)
"Lovely place. Rooms are a nice nice. We stayed in a junior suite. Pool was lovely and the view from it was incredible. Ball games etc not allowed in the pool and the pool area bar didn’t open until about 5/6pm. This is not a criticism as it created a quiet and relaxed vibe which was fitting of the ..."
Reviewed on 26 Aug 2026
Hotel Pescille by Double Hospitality
Strada Statale 47 San Gimignano SI
€137
6 Oct - 7 Oct
includes taxes & fees
9.2/10 Wonderful! (369 reviews)
"Superb stay, lovely pool, views are amazing, really nice breakfast and evening meal. Highly recommended."
Reviewed on 18 Jun 2026
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.
Frequently asked questions
How much does a Montecastelli holiday package cost?
Offering great value package deals from €460 on Expedia, you'll be thrilled with how little a holiday to Montecastelli costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Montecastelli?
January, February and November are great times to search for cheap Montecastelli holiday packages. Travelling in quieter months means you can typically find lower prices on flights and accommodation.
How many days is enough for Montecastelli?
The ideal duration of your Montecastelli holiday depends on what you'd like to see. Usually, a few days to a week will give you enough time to hit all the leading sights and explore some hidden gems along the way.
How to find the best Montecastelli package deals?
Landing a cheap Montecastelli package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Montecastelli package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Montecastelli holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and hotels individually. Better still, you can tailor your Montecastelli trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Montecastelli?
If you're planning a spontaneous Montecastelli holiday, 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 find incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Montecastelli?
- Pick your dates: What you'd like to do in Montecastelli and your preferred season will help you decide when to travel.
- Budget wisely: Besides the price of your stay, you should consider other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could arise during your trip to Montecastelli.
- Work out your trip length: Consider how much time you'd like to spend exploring Montecastelli. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Combine your accommodation and airfare: Once you've settled on your travel dates and duration, book the ideal Montecastelli holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
