Find hotels in Montecastelli from ￥11,953

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Check prices for these dates

Tonight
Dec 30 - Dec 31
Tomorrow
Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

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Our top choices for Montecastelli hotels

Royal Room, Balcony, Mountain View | Individually decorated, individually furnished, desk, cribs/infant beds
Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (1)
"Everything about this place is perfect, highly recommend."
United States
Ian
The price is ￥14,046
￥15,451 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Historic Farmhouse Casa del Chiodo
Outdoor pool, pool umbrellas, sun loungers
Agriturismo Podere Diacceroni

Agriturismo Podere Diacceroni

Agriturismo Podere Diacceroni
Peccioli
9.4 out of 10, Exceptional, (20)
"It was an incredible stay! The staff were so polite and personable. "
Canada
Lynn
The price is ￥21,400
￥23,540 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Agriturismo Podere Diacceroni
Exterior
B&B Poggiobonizio

B&B Poggiobonizio

B&B Poggiobonizio
Poggibonsi
9.2 out of 10, Wonderful, (62)
"Simone is a really nice person, he help us a lot, very friendly, room was clean, breakfast was good. "
United States
Odalis
B&B Poggiobonizio
Reception
Hotel La Magione

Hotel La Magione

Hotel La Magione
Poggibonsi
6.0 out of 10, (3)
"La vista sulle colline è bella,le camere pulite e il personale accogliente "
Italy
Gerardo
The price is ￥8,846
￥9,731 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hotel La Magione
Exterior
Hotel Albergo Italia

Hotel Albergo Italia

Hotel Albergo Italia
2.0 star property
Poggibonsi
8.4 out of 10, Very Good, (46)
"When I arrived the hotel was closed. I have had to sleep in the car"
United States
Martin
Hotel Albergo Italia
Front of property - evening/night
Hotel Toscana Ambassador

Hotel Toscana Ambassador

Hotel Toscana Ambassador
4.0 star property
Poggibonsi
8.2 out of 10, Very Good, (317)
"Wonderful breakfast. Good location!"
Canada
Karen
The price is ￥10,529
￥11,582 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hotel Toscana Ambassador
View from room
Hotel Ristorante Alcide

Hotel Ristorante Alcide

Hotel Ristorante Alcide
4.0 star property
Poggibonsi
8.0 out of 10, Very Good, (479)
"I highly recommended "
Canada
George
The price is ￥7,325
￥8,058 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hotel Ristorante Alcide
Seasonal outdoor pool, open 7 AM to 8:30 PM, pool umbrellas
Villa San Lucchese

Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (336)
"Beautiful place Great service "
United States
patricia
Villa San Lucchese
Property entrance
Le Dame del Borgo

Le Dame del Borgo

Le Dame del Borgo
Sassetta
10.0 out of 10, Exceptional, (4)
"Bellissimo appartamento in un bellissimo borgo medievale, tranquillità assoluta, la titolare disponibile per ogni vostra esigenza."
Italy
Anonymous traveler
Le Dame del Borgo
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Agriturismo Nerbona

Agriturismo Nerbona

Agriturismo Nerbona
Colle di Val d'Elsa
9.6 out of 10, Exceptional, (18)
"Very nice place"
United States
JULISSA
The price is ￥27,100
￥30,177 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Agriturismo Nerbona
Dining
Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.4 out of 10, Exceptional, (28)
"pretty setting"
Canada
ed
Valdonica Winery & Vineyard Residence
Reception
Palazzo delle Erbe

Palazzo delle Erbe

Palazzo delle Erbe
Casole d'Elsa
10.0 out of 10, Exceptional, (2)
"Very clean, nice area and excellent staff!"
United States
Bijan
The price is ￥15,791
￥17,738 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Palazzo delle Erbe
Outdoor pool, open 9:00 AM to 7:30 PM, pool umbrellas, sun loungers
B&B Ponte a Nappo

B&B Ponte a Nappo

B&B Ponte a Nappo
San Gimignano
9.4 out of 10, Exceptional, (56)
"Beautiful private property with very comfortable suites with awesome views of San Gimignano and the breathtaking valley. Highly recommend, staff was very accommodating and friendly. "
United States
Mary
The price is ￥22,574
￥25,749 total
includes taxes & fees
Jan 2 - Jan 3, 2026
B&B Ponte a Nappo
Exterior
Podere La Quercia

Podere La Quercia

Podere La Quercia
San Gimignano
10.0 out of 10, Exceptional, (15)
"Amazing stay! Clean and new rooms, and wonderful surroundings and friendly host!"
Hong Kong SAR China
So Wei
The price is ￥29,541
￥33,413 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Podere La Quercia
Seasonal outdoor pool
Agriturismo San Galgano

Agriturismo San Galgano

Agriturismo San Galgano
Chiusdino
9.0 out of 10, Wonderful, (43)
"Absolutely amazing. Even the morning was cloudy and overwhelmed with fogs, the view was spectacular with view of 'Abbaye de San Galgano'. The breakfast buffet was also more than delicious. Specifically, the salamis were cut from the staffs, not those bought from manufactured products, which also tasted great. The person who helped our check-in and -out was the only person fluent in English, but you can conversate with other staffs with no problem using your body language, don't worry about this....
Ireland
Siwoo
The price is ￥16,099
￥18,260 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Agriturismo San Galgano
Exterior
Hotel Torciano Vecchio Asilo

Hotel Torciano Vecchio Asilo

Hotel Torciano Vecchio Asilo
San Gimignano
9.6 out of 10, Exceptional, (54)
"Great boutique hotel in the middle of Tuscany. Wonderful views. The staff was very friendly and accommodating. We really loved the complimentary wine tasting at their nearby winery! We only wish their rooftop deck would’ve been open for even better views. The hotel and winery are family owned and it’s very clear that they value every guest!"
United States
Necola
Hotel Torciano Vecchio Asilo
Local cuisine
Casale San Galgano

Casale San Galgano

Casale San Galgano
Chiusdino
10.0 out of 10, Exceptional, (20)
"Peace and nature at its best"
United States
Jose Manuel
Casale San Galgano
Outdoor pool, open 8 AM to 7 PM, sun loungers
Tenuta Decimo

Tenuta Decimo

Tenuta Decimo
San Gimignano
8.2 out of 10, Very Good, (47)
"The amenities are great- pool, spa, wine tasting. The staff are friendly and were very helpful getting reservations set up."
United States
Lindsay
Tenuta Decimo
Garden
Arnolfo B&B

Arnolfo B&B

Arnolfo B&B
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (26)
"Stunning property in a cute hilltop town. Garden with tables and lounge chairs to have breakfast or hang out in the evenings. The rooms have nice details and good quality beds. "
France
Elsa
The price is ￥14,646
￥16,480 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Arnolfo B&B
Outdoor pool
Casa Vacanze Le Case

Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.0 out of 10, Wonderful, (8)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is ￥16,570
￥19,145 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Casa Vacanze Le Case
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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Top Montecastelli Hotel Reviews

Hotel Palazzo San Lorenzo & SPA

Hotel Palazzo San Lorenzo & SPA

10/10 Excellent
"Livia was amazing and made me feel very welcomed. She has great customer service skills and showed me where places were on the map. The room and bathroom was spacious."
Jillian 3-night trip
Posted 3 days ago
Hotel Palazzo San Lorenzo & SPA

More cheap stays in Montecastelli

Hotel Massa Vecchia

Hotel Massa Vecchia

Massa Vecchia, 23 Massa Marittima GR
Get rates

Frequently asked questions

What's the best place for a stay in Montecastelli?
Hotel Ristorante Alcide, located 17.1 mi (27.5 km) from the heart of Montecastelli, is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Hotel Borgo San Luigi and Hotel Italia. See all available top hotels, or vacation rentals in Montecastelli.
What are some of the best vacation home rentals in Montecastelli?
Villa with large garden in the Chianti hills: This vacation home rental outside of Montecastelli is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books. See all vacation rentals in Montecastelli.
If I need to cancel my hotel reservation in Montecastelli, will I receive a refund?
Yes! You'll find that most room reservations are refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Montecastelli.
Where can I learn more about changing or cancelling my trip to Montecastelli?
For additional details about updating your trip to Montecastelli or cancelling it, head over to our customer service page.
What's the best pet-friendly accommodation in Montecastelli?
Holiday House in Montecastelli Pisano with Private Parking is a top pet-friendly option for your stay. See more pet-friendly hotel accommodations in Montecastelli.
What are some accommodations with pools in Montecastelli?
Hotel Borgo San Luigi: Offers a children's pool, a seasonal outdoor pool, and a rooftop terrace. Poderi Arcangelo and Villa Ermellina Siena, a Tribute Portfolio Hotel are two additional hotels with an onsite pool. View all hotels with pools in Montecastelli.
What's the best hotel for staying near Peretola Airport (FLR)?
Hotel Cosmopolitan is a popular 4-star hotel featuring free WiFi and a bar. It's located a short 0.7 mi (1.2 km) from Peretola Airport. Other good choices close to the airport are Best Western Plus CHC Florence and Hotel Mirage.
How is it staying in Montecastelli?
Visitors to Montecastelli are sure to find plenty to explore and enjoy. In Montecastelli, there are 29 hotels and other accommodations to choose from. Find out more about Montecastelli.
What should I do while I'm visiting Montecastelli?
Places to visit in the wider area include Medici Fortress, Etruscan Museum, and Palazzo dei Priori. You'll also find Cathedral of Volterra and Roman Theatre in the area. Check out what more to see and do in Expedia's Montecastelli guide.
What's the weather like in Montecastelli?
The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Montecastelli is 37 inches.

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