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Our top choices for Montecastelli hotels

Villa Montarioso

Villa Montarioso
Montarioso
8.6 out of 10, Excellent, (134 reviews)
  • cleanliness
    Explore Tuscany's scenic trails from a peaceful countryside guesthouse with free breakfast.
"Quiet location not far from Siena. Has free parking and free light breakfast. "
United States
Aileen
The price is £72
includes taxes & fees
11 Mar - 12 Mar
Villa Montarioso

One Belvedere Tuscany

One Belvedere Tuscany
Poggibonsi
  • cleanliness
    Embrace Tuscan vineyard getaways with a rooftop terrace and pampering spa.
The price is £372
includes taxes & fees
6 Mar - 7 Mar
One Belvedere Tuscany

Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (1 review)
"Everything about this place is perfect, highly recommend."
United States
Ian
The price is £75
includes taxes & fees
15 Feb - 16 Feb
Historic Farmhouse Casa del Chiodo

Capanna 1826

Capanna 1826
San Gimignano
10.0 out of 10, Exceptional, (43 reviews)
  • cleanliness
    Scenic wine retreat in Tuscany with daily gourmet breakfast and lush gardens.
"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
Capanna 1826

Agriturismo il Poggiarello

Agriturismo il Poggiarello
Siena
9.4 out of 10, Exceptional, (22 reviews)
  • cleanliness
    Tuscan farm stay near Siena with seasonal pool and mountain biking trails.
"Mariangela, the hostess was so kind and attentive. Sara took care of our rooms and wonderful breakfasts everyday. This property has amazing views of the Siena/Tuscan courtside and an amazing pool that was so beautiful. Had no trouble getting a taxi to explore the area. Can't wait to come visit again!"
United States
Karen
The price is £178
includes taxes & fees
6 Mar - 7 Mar
Agriturismo il Poggiarello

Urban Stay Siena

Urban Stay Siena
Petriccio
The price is £68
includes taxes & fees
16 Mar - 17 Mar
Urban Stay Siena

Villa Sabolini

Villa Sabolini
4.0 star property
Colle di Val d'Elsa
9.2 out of 10, Wonderful, (189 reviews)
  • cleanliness
    Tranquil countryside retreat with panoramic views and poolside relaxation.
"Beautiful location and hotel Staff were excellent - thank you"
United Kingdom
Amit
The price is £85
includes taxes & fees
1 Mar - 2 Mar
Villa Sabolini

Hotiday Toscana Riparbella

Hotiday Toscana Riparbella
Riparbella
10.0 out of 10, Exceptional, (2 reviews)
"Personale"
Italy
Michael
The price is £33
includes taxes & fees
19 Feb - 20 Feb
Hotiday Toscana Riparbella

La Canonica di San Michele

La Canonica di San Michele
Monteriggioni
10.0 out of 10, Exceptional, (46 reviews)
  • cleanliness
    Contemporary Tuscan B&B with a scenic rooftop terrace and poolside relaxation.
"Fantastic hospitality and very welcoming. Very much worth staying at! "
United States
James
La Canonica di San Michele

Agriturismo Pelagaccio

Agriturismo Pelagaccio
Peccioli
  • cleanliness
    Savour Italian countryside charm with a seasonal outdoor pool in scenic Peccioli.
The price is £128
additional charges may apply
28 Feb - 1 Mar
Agriturismo Pelagaccio

Relais dei Molini

Relais dei Molini
Castagneto Carducci
10.0 out of 10, Exceptional, (7 reviews)
  • cleanliness
    Tuscan coast B&B offers hiking trails, hot tubs, and complimentary breakfast.
"We were upgraded to a suite which was great. We were the only guests at the resort and got extra attention. The accommodations and breakfast were next level - we would definitely stay again. Luca was a pleasure to speak with and very knowledgeable."
Canada
DOUG
Relais dei Molini

Albergo Etruria

Albergo Etruria
3.0 star property
Volterra
9.6 out of 10, Exceptional, (169 reviews)
  • cleanliness
    Experience Volterra's beauty with a view from the rooftop terrace.
"Lovely staff. Excellent location."
United States
vicky
The price is £74
includes taxes & fees
1 Mar - 2 Mar
Albergo Etruria

B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.4 out of 10, Exceptional, (16 reviews)
  • cleanliness
    Rustic Tuscan B&B near Sassoforte Castle with on-site dining and free breakfast.
"Ras"
France
jean
The price is £49
includes taxes & fees
8 Mar - 9 Mar
B&B da Nada Locanda Toscana

Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (33 reviews)
  • cleanliness
    Tuscan countryside retreat with vineyard views and authentic Italian dining in Monteriggioni.
"Very nice staff and very nice place to stay."
United Kingdom
Ryan
The price is £88
includes taxes & fees
9 Mar - 10 Mar
Hotel Ristorante La Dama nella Vigna

B&B Suvereto

B&B Suvereto
Suvereto
The price is £89
includes taxes & fees
20 Feb - 21 Feb
B&B Suvereto

Relais Le Macine di Stigliano

Relais Le Macine di Stigliano
4.0 star property
Sovicille
10.0 out of 10, Exceptional, (15 reviews)
  • cleanliness
    Unwind at this Tuscan gem with a rooftop terrace and seasonal outdoor pool.
"Excellent hotel in a beautiful picturesque little town Hotel was very nice and comfortable, beautiful decor to the the smallest detail Views were beautiful, air was crisp Breakfast was delicious Free parking on site Would definitely stay here again "
United States
Susan
The price is £149
includes taxes & fees
8 Mar - 9 Mar
Relais Le Macine di Stigliano

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
  • cleanliness
    Enjoy a seasonal pool and complimentary breakfast at this charming Siena retreat.
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea

Mormoraia

Mormoraia
San Gimignano
9.6 out of 10, Exceptional, (209 reviews)
  • cleanliness
    Tuscan farm stay with winery, spa, and stunning San Gimignano views.
"Beautiful property! "
United States
Karen
The price is £215
includes taxes & fees
11 Mar - 12 Mar
Mormoraia

Agriturismo Cotorniano

Agriturismo Cotorniano
Casole d'Elsa
The price is £152
includes taxes & fees
14 Feb - 15 Feb
Agriturismo Cotorniano

Castel Pietraio

Castel Pietraio
Monteriggioni
9.2 out of 10, Wonderful, (33 reviews)
  • cleanliness
    Charming farmhouse stay in Monteriggioni with pool and restaurant on-site.
"Beautiful grounds, friendly staff."
United States
austin
Castel Pietraio
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

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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 £42 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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