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22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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Our top choices for Montecastelli hotels

Breakfast, dinner served; Regional cuisine, garden views
Poderi Arcangelo

Poderi Arcangelo

Poderi Arcangelo
San Gimignano
9.0 out of 10, Wonderful, (326)
Immerse yourself in authentic Tuscany at this San Gimignano farm stay featuring 3 refreshing outdoor pools. Sample regional cuisine at the on-site restaurant after exploring nearby Casa del Boccaccio. Enjoy free WiFi, convenient parking, and service from the highly-praised staff.
"The staff was very knowledgeable and fantastic. The location is beautiful and we will definitely be booking again. "
United States
justin
Poderi Arcangelo
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Tenuta Sovestro - Agriturismo e Winery

Tenuta Sovestro - Agriturismo e Winery

Tenuta Sovestro - Agriturismo e Winery
San Gimignano
9.6 out of 10, Exceptional, (43)
Set among San Gimignano's rolling hills, this charming agriturismo offers wine tastings from its own winery and relaxing days by the seasonal pool. Enjoy free breakfast and WiFi while being just a short drive from Poggibonsi-San Gimignano Station.
"Beautiful property with the most wonderful staff!!!!"
United States
dana
The price is ฿4,129
฿4,726 total
includes taxes & fees
19 Jan - 20 Jan 2026
Tenuta Sovestro - Agriturismo e Winery
Exterior
Duccio Nacci Rooms - guest house

Duccio Nacci Rooms - guest house

Duccio Nacci Rooms - guest house
San Gimignano City Centre
9.8 out of 10, Exceptional, (6)
Steps from Galleria Continua and Medieval Criminal and Torture Museum, this guesthouse offers a charming Italian retreat. Free WiFi and housekeeping services ensure a comfortable, convenient stay in the heart of Tuscany.
The price is ฿3,641
฿4,189 total
includes taxes & fees
23 Dec - 24 Dec
Duccio Nacci Rooms - guest house
Garden
Podere La Quercia

Podere La Quercia

Podere La Quercia
San Gimignano
10.0 out of 10, Exceptional, (15)
Immerse yourself in the Italian countryside at this charming San Gimignano farm stay. Enjoy active pursuits with on-site mountain biking, then refuel with daily buffet breakfast. Near Tenuta Torciano Winery and just a 13-minute drive from Certaldo Station.
"Amazing stay! Clean and new rooms, and wonderful surroundings and friendly host!"
Hong Kong SAR China
So Wei
The price is ฿5,917
฿6,693 total
includes taxes & fees
14 Jan - 15 Jan 2026
Podere La Quercia
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)
Discover rural Tuscan charm at this countryside retreat with a refreshing seasonal pool, free bike rentals, and volleyball court. Perfectly positioned near Archaeological Museum and Il Palagio Winery, with convenient parking for day trips.
"Very nice place"
United States
JULISSA
The price is ฿3,045
฿3,423 total
includes taxes & fees
23 Dec - 24 Dec
Agriturismo Nerbona
Lobby lounge
Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.4 out of 10, Exceptional, (28)
Immerse yourself in wine country at this Roccastrada farmhouse featuring an on-site winery and restaurant. Enjoy complimentary breakfast before relaxing by the seasonal outdoor pool or scheduling a massage at the spa. The bar, terrace, and free WiFi enhance your Tuscan retreat.
"pretty setting"
Canada
ed
Valdonica Winery & Vineyard Residence
Front of property – evening/night
Relais Le Macine di Stigliano

Relais Le Macine di Stigliano

Relais Le Macine di Stigliano
4.0 star property
Sovicille
10.0 out of 10, Exceptional, (15)
Located near Val di Merse, this Sovicille hotel offers a hot tub and sauna alongside elegant dining options. Enjoy complimentary breakfast, WiFi, and parking while exploring nearby attractions from this serene countryside retreat.
"Amazing staff. Beautiful views and facilities. Treated like friends. "
United States
Josh
The price is ฿4,173
฿4,774 total
includes taxes & fees
23 Dec - 24 Dec
Relais Le Macine di Stigliano
Front of property
Villa Nencini

Villa Nencini

Villa Nencini
Volterra
8.4 out of 10, Very good, (56)
Experience panoramic views from the terrace of this Volterra hotel, complete with a refreshing seasonal outdoor pool and convenient bar. Enjoy Italian cuisine at the restaurant after exploring nearby Rossi Alabastri Volterra and Alabaster Ecomuseum attractions.
"Beautiful property, plenty of parking spaces, walkable very to close to Volterra historic town. "
United States
Juan
The price is ฿2,377
฿2,799 total
includes taxes & fees
23 Dec - 24 Dec
Villa Nencini
Terrace/patio
Albergo Etruria

Albergo Etruria

Albergo Etruria
3.0 star property
Volterra
9.6 out of 10, Exceptional, (168)
Located in historic Volterra, this charming hotel offers a rooftop terrace with stunning views. Unwind at the bar or visit the café for a bite. Near Torre del Porcellino and Palazzo Incontri Viti, guests enjoy free breakfast, WiFi, and parking.
"Beautiful hotel, you have to stay here. Rooms are immaculate, staff go above and beyond, from reception to roof terrace. Absolutely love love this hotel."
United Kingdom
Rose
The price is ฿2,795
฿3,258 total
includes taxes & fees
23 Dec - 24 Dec
Albergo Etruria
Front of property
Relais Della Rovere

Relais Della Rovere

Relais Della Rovere
4.0 star property
Colle di Val d'Elsa
9.0 out of 10, Wonderful, (243)
Elegant Italian hotel adjacent to golf course featuring outdoor pool and authentic cuisine at Il Cardinale restaurant. Enjoy free breakfast, WiFi and parking while exploring nearby Sentierelsa Trail and Piazza Arnolfo di Cambio, just minutes from Monteriggioni.
"Quietly located hotel with modern rooms and very good dinner option in the courtyard. Spacious pool to relax after long sightseeing days in the countryside."
Germany
Alexander
Relais Della Rovere
Front of property
Hotel Borgo San Luigi

Hotel Borgo San Luigi

Hotel Borgo San Luigi
4.0 star property
Monteriggioni
9.2 out of 10, Wonderful, (405)
Set among Monteriggioni's rolling hills, this Tuscan hotel offers Italian dining at LA BIANCA RESTAURANT and a poolside bar. Tennis courts, free breakfast, and helpful staff create a memorable stay near Le Caldane Thermal Baths.
"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "
United States
Allyson
Hotel Borgo San Luigi
Exterior
Villa le Camelie Siena

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8)
Located just a 16-minute walk from Siena Station, this welcoming villa offers free WiFi and daily housekeeping. Enjoy satellite TV while staying near popular attractions like Siena Stadium and Palasport Mens Sana.
"Personal people are very good. "
Switzerland
Wenjuan
The price is ฿2,858
฿3,291 total
includes taxes & fees
23 Dec - 24 Dec
Villa le Camelie Siena
Balcony
Palazzo al Torrione 2

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (107)
Located steps from Historical Torture Museum and Museum San Gimignano 1300, this affittacamere offers free WiFi and comfortable rooms with daily housekeeping. Enjoy easy access to Florence Airport and Poggibonsi-San Gimignano Station.
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is ฿2,959
฿4,358 total
includes taxes & fees
19 Jan - 20 Jan 2026
Palazzo al Torrione 2
Deluxe Apartment, 1 Bedroom, Non Smoking, Hot Tub | In-room safe, blackout curtains, iron/ironing board
San Sebastiano Suite & Luxury

San Sebastiano Suite & Luxury

San Sebastiano Suite & Luxury
Colle di Val d'Elsa
8.6 out of 10, Excellent, (7)
Experience the heart of Tuscany at this intimate B&B, steps from Museo del Cristallo and historic Piazza Arnolfo di Cambio. Enjoy modern comforts with free WiFi and climate control while exploring this medieval gem between Florence and Poggibonsi.
"Great location and beautiful place to stay. Loved the interior decorating and host was good too. Would stay again. "
Canada
Nadia
San Sebastiano Suite & Luxury
Double Room | Desk, iron/ironing board, rollaway beds, free WiFi
Palazzo Mari

Palazzo Mari

Palazzo Mari
San Gimignano City Centre
9.8 out of 10, Exceptional, (77)
Located near Archaeological Museum and Piazza delle Erbe, this cosy B&B offers thoughtful amenities including slippers and daily housekeeping. Enjoy complimentary WiFi while exploring the enchanting medieval surroundings of San Gimignano.
"Great location in a wonderful medieval town.. Just keep in mind that there are stairs and hills in this amazing destination."
Canada
Denis
Palazzo Mari
Terrace/patio
Casa di Campagna in Toscana

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (19)
Unwind at this rustic Sovicille retreat offering regional cuisine at Grillo Moro restaurant. Splash in the seasonal pool, borrow free bikes to explore, or sip drinks at the bar. San Leonardo al Lago and Porta Tufi attractions are just a short drive away.
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana
Restaurant
Locanda dell'Aioncino

Locanda dell'Aioncino

Locanda dell'Aioncino
Bibbona
10.0 out of 10, Exceptional, (23)
Immerse in coastal tranquility at this Bibbona B&B offering complimentary breakfast, WiFi, and parking. Explore nearby Bolgheri Castle or tee off at Golf Club Le Capanne before returning to this relaxing countryside retreat just 15 minutes from the station.
"beautiful location, friendly staff, comfortable room, excellent breakfast, i look forward to coming back!"
United States
Anonymous traveller
Locanda dell'Aioncino
Daily self-service breakfast (EUR 6 per person)
Beatabb

Beatabb

Beatabb
Guardistallo
9.0 out of 10, Wonderful, (7)
Experience Italian charm at this aparthotel near La Regola Azienda Vitivinicola. Apartments include LCD TVs, dressing gowns, and free WiFi. Enjoy breakfast options and daily housekeeping while exploring nearby attractions and Parco Gallorose.
"The host was lovely and this was the most beautiful place to stay and wish we had stayed longer "
United Kingdom
Sheena
Beatabb
Terrace/patio
B&B Poggiobonizio

B&B Poggiobonizio

B&B Poggiobonizio
Poggibonsi
9.2 out of 10, Wonderful, (62)
Wake up to continental breakfast at this welcoming Poggibonsi retreat. Just 4 minutes from the train station, with free WiFi and parking. Explore nearby Archeodromo di Poggibonsi and Fountain of Fate during your business or leisure stay.
"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
Comfort Apartment, 1 Bedroom (Le Viole) | Terrace/patio
Affittacamere Le Ginestre

Affittacamere Le Ginestre

Affittacamere Le Ginestre
San Gimignano City Centre
7.8 out of 10, Good, (6)
Steps from the Ornithological Museum, this inviting affittacamere welcomes adventurers with free WiFi and convenient laundry facilities. Explore local trails or stroll to Museum San Gimignano 1300, then relax in rooms serviced by daily housekeeping.
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
Affittacamere Le Ginestre
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 Borgo San Luigi

Hotel Borgo San Luigi

10/10 Excellent
"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "
Allyson 3-night trip
Posted 3 weeks ago
Hotel Borgo San Luigi

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 traveller 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.
If I need to cancel my hotel reservation in Montecastelli, will I receive a refund?
Yes, the majority of hotel reservations are refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If you have a non-refundable reservation, you might still have the option to cancel and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Montecastelli.
What are some accommodation options 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 on-site pool. View all hotels with pools in Montecastelli.
What's it like to stay in Montecastelli?
Visitors to Montecastelli will definitely find plenty to explore and enjoy. In Montecastelli, there are 30 hotels and other accommodation options 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 Porta all'Arco. You'll also find Palazzo dei Priori and Cathedral of Volterra in the area. Take a look at what more there is to see and do in Expedia's Montecastelli guide.
What's the seasonal weather like in Montecastelli?
The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Montecastelli is 935 mm.