Montecastelli

Travel Guide

Poderi Arcangelo

Poderi Arcangelo

Localita Capezzano San Gimignano SI
$108 nightly
The price is $124 total per night from Nov 8 to Nov 9
$124 total
Nov 8 - Nov 9
Total with taxes and fees
Book a stay at this family-friendly farm stay in San Gimignano. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our ...
9/10 Wonderful! (379 reviews)
"Beautiful property, nice and helping staff. We enjoy our stay ."

Reviewed on Oct 1, 2026

Poderi Arcangelo
Hotel Italia

Hotel Italia

3 out of 5
Viale Camillo Benso Conte di Cavour, 67 Siena SI
$83 nightly
The price is $95 total per night from Nov 1 to Nov 2
$95 total
Nov 1 - Nov 2
Total with taxes and fees
Stay at this hotel in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,001 reviews)
"We stayed here for three nights and absolutely loved it. The hotel is charming, convenient and comfortable. Breakfast was very good, with a nice choice of foods, and the lounge/bar is a great place to relax. The staff were very helpful with directions and bookings. We would gladly stay here ..."

Reviewed on Oct 10, 2026

Hotel Italia
Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

4 out of 5
Via Custoza 2 Siena SI
$153 nightly
The price is $171 total per night from Nov 3 to Nov 4
$171 total
Nov 3 - Nov 4
Total with taxes and fees
Book a stay at this family-friendly hotel in Siena. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Villa Ermellina Siena, a Tribute Portfolio Hotel
See all 4,306 properties in Montecastelli
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.
ApartHotel Anghel

ApartHotel Anghel

via Paolo Frajese 71 Siena SI
Book a stay at this business-friendly apartment in Siena. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Piazza del Campo and National ...
ApartHotel Anghel
Camping Boschetto Di Piemma

Camping Boschetto Di Piemma

3 out of 5
Localita' Santa Lucia 38C San Gimignano SI
Stay at this campground in San Gimignano. Enjoy free parking, 2 bars/lounges, and a garden. Popular attractions Sovestro in Poggio Winery and Tenuta Sovestro ...
8.8/10 Excellent! (91 reviews)
"The mobile homes were a great alternative when Via Francigena hostels were full. Friendly people, swimming pool was wonderful , and an easy walk back and forth to San Gimignano."

Reviewed on Jun 24, 2025

Camping Boschetto Di Piemma
Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

Siena Tuscany
Book a stay at this family-friendly vacation home in Castellina in Chianti. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Lilliano Estate ...
9.6/10 Exceptional! (82 reviews)
"Wir waren als Familie mit 2 Teenager-Kindern eine gute Woche hier und fanden es super! Das Haus und vorallem der Garten sind traumhaft. Der Pool ist ein paar Schritte entfernt und wird mit anderen geteilt, was völlig okay war. Zum Haus gehört eine Katze, die jeden Morgen an der Terrassentür wartet, ..."

Reviewed on Aug 31, 2026

Villa with large garden in the Chianti hills
See all properties in Montecastelli
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

When is the best time to visit Montecastelli?
The best time to visit Montecastelli is from May through September, when the climate is most pleasant for travelers. For fewer crowds and better value, the quieter months of November through February are a good option, offering a more relaxed experience with cooler temperatures.
Can I book a refundable hotel in Montecastelli?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Montecastelli by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Montecastelli with Expedia?
Expedia makes it easier to plan your Montecastelli trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Montecastelli?
The best choice depends on your travel style. Hotels in Montecastelli can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Montecastelli trip on Expedia?
Once you've booked your Montecastelli trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Montecastelli trip?
Expedia offers customer support before, during, and after your Montecastelli trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Montecastelli?
If it's your first trip to Montecastelli, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Montecastelli hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Montecastelli hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Montecastelli

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