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Our top choices for Montecastelli hotels

Hotiday Massa Marittima

Hotiday Massa Marittima
Massa Marittima
The price is CA $60
CA $78 total
includes taxes & fees
Apr 14 - Apr 15
Hotiday Massa Marittima

Locanda Casalta

Locanda Casalta
Strove
The price is CA $170
CA $187 total
includes taxes & fees
Apr 14 - Apr 15
Locanda Casalta

agriturismo e maneggio Poggio Leone

agriturismo e maneggio Poggio Leone
Gambassi Terme
The price is CA $252
CA $282 total
includes taxes & fees
Apr 14 - Apr 15
agriturismo e maneggio Poggio Leone

AGRITURISMO CESANI

AGRITURISMO CESANI
San Gimignano
The price is CA $168
CA $193 total
includes taxes & fees
Apr 14 - Apr 15
AGRITURISMO CESANI

B&B Suvereto

B&B Suvereto
Suvereto
The price is CA $144
CA $162 total
includes taxes & fees
Apr 21 - Apr 22
B&B Suvereto

Villa Sabolini

Villa Sabolini
4.0 star property
Colle di Val d'Elsa
9.2 out of 10, Wonderful, (196 reviews)
"Beautiful Tuscan estate, lovely room, excellent breakfast "
Canada
Ariel
The price is CA $194
CA $220 total
includes taxes & fees
Apr 28 - Apr 29
Villa Sabolini

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (35 reviews)
"Very nice staff and very nice place to stay."
United Kingdom
Ryan
The price is CA $174
CA $199 total
includes taxes & fees
May 3 - May 4
Hotel Ristorante La Dama nella Vigna

Villa Montarioso

Villa Montarioso
Montarioso
8.6 out of 10, Excellent, (135 reviews)
"Quiet location not far from Siena. Has free parking and free light breakfast. "
United States
Aileen
The price is CA $115
CA $135 total
includes taxes & fees
May 12 - May 13
Villa Montarioso

Capanna 1826

Capanna 1826
San Gimignano
10.0 out of 10, Exceptional, (43 reviews)
"It’s a great place to serve as a base if you plan to see San Gimignano, Siena, Voltaire, Florence, Lucca, and Pisa. The service was outstanding and the room was very clean. "
United States
Jim
The price is CA $151
CA $183 total
includes taxes & fees
Apr 15 - Apr 16
Capanna 1826

B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.4 out of 10, Exceptional, (16 reviews)
"Ras"
France
jean
The price is CA $85
CA $97 total
includes taxes & fees
Apr 14 - Apr 15
B&B da Nada Locanda Toscana

Hotiday Toscana Riparbella

Hotiday Toscana Riparbella
Riparbella
9.0 out of 10, Wonderful, (10 reviews)
"It was nice. The staff was friendly, but the brochures need to be updated with the correct pricing, also it would be nice to know that they don’t provide certain spa services when you’re the only one asking for it. If I had know that and that the restaurants were closed most of the time, I probably would’ve gone where it was more consistent."
United States
Zi'yah
The price is CA $80
CA $88 total
includes taxes & fees
Apr 14 - Apr 15
Hotiday Toscana Riparbella

One Belvedere Tuscany

One Belvedere Tuscany
Poggibonsi
The price is CA $679
CA $754 total
includes taxes & fees
May 12 - May 13
One Belvedere Tuscany

Albergo Etruria

Albergo Etruria
3.0 star property
Volterra
9.6 out of 10, Exceptional, (173 reviews)
"Lovely hotel. The owners are very kind and helpful. They offered great recommendations for the area. Paola and Danielle were so kind. The rooms were well appointed and the daily breakfast was delicious! Would definitely stay here again!"
United States
Jeanne
The price is CA $165
CA $190 total
includes taxes & fees
Apr 15 - Apr 16
Albergo Etruria

Hotel Torciano Vecchio Asilo

Hotel Torciano Vecchio Asilo
San Gimignano
9.6 out of 10, Exceptional, (54 reviews)
"Cute hotel, breakfast was okay, the winery is incredible (not located at the hotel, but very close). Overall, would come back. "
United States
Devin Jordan
The price is CA $335
CA $378 total
includes taxes & fees
Apr 21 - Apr 22
Hotel Torciano Vecchio Asilo

Agrihotel Il Palagetto

Agrihotel Il Palagetto
3.0 star property
Volterra
8.6 out of 10, Excellent, (84 reviews)
"Amazing views, very nice staff and good food. Room was ok. A little dark and humid. "
United States
Patrick
The price is CA $119
CA $139 total
includes taxes & fees
Apr 14 - Apr 15
Agrihotel Il Palagetto

Borgo Pignano Volterra Tuscany

Borgo Pignano Volterra Tuscany
5.0 star property
Volterra
10.0 out of 10, Exceptional, (89 reviews)
"Great breakfast and dining options offered. Enjoyed the activities and the gym. "
South Korea
Jae Wook
The price is CA $609
CA $678 total
includes taxes & fees
Apr 15 - Apr 16
Borgo Pignano Volterra Tuscany

Locanda Il Pino

Locanda Il Pino
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
The price is CA $114
CA $133 total
includes taxes & fees
Apr 15 - Apr 16
Locanda Il Pino

Il Defizio

Il Defizio
Gambassi Terme
9.8 out of 10, Exceptional, (60 reviews)
"Fantastic place. The dinner was tve best we had all week"
Denmark
Leif
The price is CA $179
CA $202 total
includes taxes & fees
May 4 - May 5
Il Defizio

GLAMPING PIAN DELLE GINESTRE

GLAMPING PIAN DELLE GINESTRE
Sassetta
The price is CA $176
CA $202 total
includes taxes & fees
Apr 19 - Apr 20
GLAMPING PIAN DELLE GINESTRE

Urban Stay Siena

Urban Stay Siena
Petriccio
9.0 out of 10, Wonderful, (2 reviews)
"Il massimo del confort "
Italy
Fabio
The price is CA $116
CA $135 total
includes taxes & fees
Apr 24 - Apr 25
Urban Stay Siena
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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Frequently asked questions

What is the best area to stay in Montecastelli?
The best area to stay in Montecastelli is directly within the village of Montecastelli Pisano itself, or in the immediate surrounding countryside.

Montecastelli Pisano is a small, historic hilltop village that offers a truly authentic Tuscan experience. It's built around a medieval castle and features narrow, cobbled streets, stone houses, and stunning views of the countryside. The village is compact and can be explored on foot, with a few local eateries and a church at its heart.

For couples seeking a romantic and peaceful retreat, staying within the village provides a unique opportunity to experience Tuscan life. You'll wake up to the sounds of the village and enjoy evenings strolling the quiet streets, perhaps enjoying a local meal with panoramic views. The sense of history and the relaxed pace are particularly appealing here.

Alternatively, for families or those who prefer more space and amenities, the countryside immediately surrounding Montecastelli offers excellent options. Many renovated farmhouses and villas (often called 'agriturismi') are available, typically offering private pools, extensive gardens, and more room for children to play.
When is the best time to go to Montecastelli?
The best time to visit Montecastelli is typically during the shoulder seasons of late April to early June and September to early October.

During these months, you'll experience pleasant weather, ideal for exploring the Tuscan countryside without the intense heat of summer. The landscapes are particularly beautiful, with blooming wildflowers in spring and the colours of the harvest season in autumn. This period also avoids the busiest tourist crowds, making for a more peaceful and enjoyable visit.

For those prioritising outdoor activities like hiking, cycling, or enjoying al fresco dining, these shoulder months offer comfortable temperatures. The vineyards are either budding with new growth or heavy with ripe grapes, providing excellent photo opportunities and a chance to experience the region's agricultural rhythm.

While July and August offer consistently warm weather for poolside relaxation, they can be very hot and busier, especially at popular attractions.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Montecastelli.
How can I save on a Montecastelli hotel booking with Expedia?
Members always get our best prices. Find our best Montecastelli hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Montecastelli hotel?
Prices for hotels in Montecastelli often vary, but you can find a great deal from CA $88 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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